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Holiday Rentals with Pools in Key West

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    268 Matching Rentals in Key WestView all 331 rentals
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    1/2 Block to Duval, World of its own -Nassau Suite1 / 17
    (32)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Best Location, 1/2 Block to Duval, Bimini Suite1 / 17
    (48)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Center of It All - Paradise Island Suite1 / 14
    (31)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Steps to Duval, Old Town Charm -Grand Bahama Suite1 / 11
    (60)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    • Balcony
    • Parking
    • Washer
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 June 2018
    We stayed 3 nights in the Grand Bahama Suite. There were 3 couples. We had an awesome time! Steps to Duval Street and the pool was awesome!! We were fortunate enough to work...
    Reviewed 24 May 2018
    We love, love, love this place. Comfortable beds, everything we needed we had. Pool was perfect temperature and kept pristine. We liked having a washer and dryer. We were close...
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    About this property
    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable...
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    33040, Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sunrise Suite Key West 2 Bed Rooms 2 Full Baths1 / 25
    (67)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The unit was just as advertised, clean, easy check in. We had a great time and would definitely book this again.
    Reviewed 3 weeks ago
    Great location! In the action but out of sight! Plenty of room for our family and kid friendly and safe! Clean and maintained. Close enough to all locations (5-10 min drive...
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    About this property
    Our unit is a 2 bedroom 2 bathroom condominium with a full kitchen. Located in Key West, FL for Nightly, Weekly, vacation rental. The price of a hotel with the comforts of home. Sunrise Suite Key West is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a...
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage1 / 39
    (39)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Waterfront
    • Air Conditioning
    • Sauna
    • Washer
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2017
    Kathy and Bob have a great large two bedroom condo with generous resources; tv in each room, radios, games, wet bar, great space for cooking and lots of beach supplies: bikes...
    Reviewed 17 June 2017
    Everything with this rental was first rate from start to finish. Kathy, the owner, checked in with us multiple times in the weeks leading up to our arrival to make sure we knew...
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    About this property
    This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is oceanfront with an Olympic...
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Isle Of View II1 / 24
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • DVD Player
    • Secure Parking
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    First, I would like to apologize to both Jeff and Kelly for taking so long to write this review. The experience could not have been better. It was extremely easy to get...
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    About this property
    Luxurious and spacious accommodations aboard this elegantly designed 45' Morgan Nelson Marek sailing vessel. Moored on first class dock space in front of the newly constructed Key West Perry Hotel, your stay will begin with welcome and cocktails as you board. Once you've settled, make your way to...
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunrise At Seaside Condo 2 bedroom 2 bath1 / 12
    (29)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    • Terrace
    • Hot Tub
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Love this place and the property manager she was real nice and helpful the view of the airport and the ocean was amazing
    Reviewed 7 July 2018
    The condo was convinced to everything full kitchen loved it saved lots of doe cooking in instead of going out for every meal forth floor was a good work out elevators worked...
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    About this property
    Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small boats on trailer allowed....
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Key West Condo close to the Ocean1 / 26
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Balcony
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 March 2018
    This is the second time we have stayed at this property, the first being in 2016. It still is a conveniently located, quiet and peaceful condo with reserved parking. It is...
    Reviewed 25 January 2017
    Found Key West absolutely enchanting, and this little condo was in a perfect location to get to the hustle and bustle of downtown Key West, but be able to retire to a quieter...
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    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach. This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony...
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Escape1 / 26
    (85)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2017
    This place is just perfect! Nice and clean, and check in was a breeze! But what I really loved about it is the location! You are in Key West, but you are far enough away from...
    Reviewed 7 July 2017
    Owners were great and very accommodating. The condo is beautiful. Has everything you need. Pool was great to use. We would rent again when we come to key West. We had a great...
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    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Shelleys Rooftop Hideaway1 / 15
    (7)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Porch
    • Balcony
    • Parking
    • Outdoor Dining Area
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2018
    This is a really good location! Really nice accommodations and a really nice porch to relax on. The family enjoyed how close we were to the beach at the southern most point...
    Reviewed 17 November 2017
    We thoroughly enjoyed our stay in this location. It was a roomy, clean, convenient condo. It was comfortable and felt like our home. Will definitely stay again if the...
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    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Keys Yacht Vacations! 3 BR (4bed) 2 BA Luxury Yacht-Sunset Cruise avail1 / 18
    (8)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Washer
    • Waterfront
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2018
    We had such a wonderful time! The yacht is very nicely equipped & we all slept very comfortably! The marina is top notch too! The first day we arrived, a manatee came right...
    Reviewed 19 January 2016
    We had such a great time staying on the Key West Yacht and Breakfast, It was definitely a different experience staying on a boat but we had such an amazing time. It was so...
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    About this property
    Tourism permitted again starting Oct 1! Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. IF TRAVELING WITHIN 10 days please contact us for reduced rates! Cruises can be added on for additional fee. Fully equipped from bow to stern -- Galley (kitchen to the...
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Oceanfront 2 Bedroom 2 Bath Condo Key West Florida1 / 34
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Waterfront
    • Sauna
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2018
    Great super clean condo located directly across from Smathers Beach for those who want walking access to beach OR hot tub and pool access directly in secure gated community. You...
    Reviewed 18 March 2018
    This condo is everything we were looking for and more. The beachfront location was a prefect place to watch the sunrise. Nights were quiet and peaceful. The pool area was great...
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    About this property
    The 'SeaJay' at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers...
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Coral Hammock was built in 2004. This home is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 1 king size beds and 2 queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils. There is a new Whirlpool Duet washer/dryer...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Truman Annex Shipyard with Tropical Garden1 / 8
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2017
    We love staying here. There was plenty of room and the condo was nicely decorated. We walked and biked all over with ease -- great location.
    Reviewed 16 May 2017
    Love love loved the town house. Beautiful. Love cation was perfect. Was able to walk most everywhere. Felt safe walking late at night also. Beautiful location. Can't wait to...
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    About this property
    Decorated in shade of sea foam and coral, this property is located in the Truman Annex and puts all of Key West's top attraction within easy walking distance. French doors open to a garden with hibiscus and cat palms framing a comfortable patio. Both bedrooms have queen beds, with a sofa bed in...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Key West Florida Beachfront Condo1 / 22
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Sauna
    • Ocean Views
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 June 2018
    Mrs Carol thank you for the beautiful place to stay in for a beautiful trip. The views were awesome from the room. The sunsets you can watch from balcony was dream like. Highly...
    Reviewed 24 October 2017
    I went to Key West with four other childhood friends for a 50th celebration! We booked our week five months prior, and of course hurricane Irma ravaged the Island. We...
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    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sunrise at Seaside Condo 2 Bedroom1 / 13
    (24)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Washer
    • Balcony
    • Internet Access
    • Air Conditioning
    • Parking
    • Grill
    • Outdoor Dining Area
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2018
    Condo was wonderful. Pool beautiful. We were far enough from Duval St. to have plenty of peace and quiet and near enough to be there whenever we wanted. Condo had everything we...
    Reviewed 18 November 2017
    I would stay there again. Pool was also nice. Bonnie was always assessable And Easy to talk to. Plenty of room inside. Washer and dryer and full kitchen
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    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    SPECIAL DISCOUNT!  45' Luxury Sailing Yacht and Other Yachts & Boats1 / 19
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Balcony
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2018
    Husband and I enjoyed our recent five-day stay on The Lion’s Paw - a new and unique experience for us compared to the typical lodging options we normally choose. It was really...
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    About this property
    This yacht is very spacious and bright with windows surrounding it making views of the ocean amazing. The marina and its grounds are meticulous and located in the middle of a turquoise paradise with amazing water clarity. Your stay will include free access to the marina's private pool,...
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    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elegant, Two Bedroom Condo Close to the Ocean1 / 17
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • Washer
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2016
    Overall we were satisfied with our stay at this condo, but there were pros and cons. Pros: The layout was nice, almost like 2 separate hotel rooms joined by a shared kitchen...
    Reviewed 14 July 2016
    This condo was amazing. The service provided was excellent. I loved the location and it was just what i was looking for. Knowing we had a great place to stay made the trip even...
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    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This yacht is very spacious and bright with windows surrounding it making views of the ocean amazing. The marina and its grounds are meticulous and located in the middle of a turquoise paradise with amazing water clarity. Your stay will include free access to the marina's private pool,...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Welcome Aboard!  Relax, unwind, enjoy the water! in key west1 / 50
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Loved Jen and Mitch! Very welcoming! Made everything very comfortable and relaxing! Thier friends and neighbors are very nice and welcoming too! We enjoyed a cookout, a...
    Reviewed 13 April 2018
    My husband and I enjoyed a 3 day stay on the Fat and Sassy. The owners are welcoming and helpful with any questions or recommendations you it need. The marina is perfect, with a...
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    About this property
    Join us in Key West where we are docked at a beautiful Marina. Enjoy all the comforts of home and the added beauty of the Ocean. There are pools and a Waterfront Bar & Grill for your enjoyment. We will be Aboard in the private owner’s suite to make sure your stay is hassle free and exciting....
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access1 / 27
    (18)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Waterfront
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2017
    Perfect stay for all of us. The kitchen was perfect for our meals. We all slept very comfortable and we enjoyed the decorating that has been done. We enjoyed all the different...
    Reviewed 11 January 2017
    Very cool and unique lodging. Not luxury but very nice and clean. Great communication with host. Very friendly. Great decks/outdoor spaces on boat.
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    About this property
    The M/V Coconuts is a completely unique home with 360 degree water views. It also happens to be an exceedingly rare 50-foot Florida Bay Coaster Trawler permanently docked at the Key West Harbour Yacht Club, featuring a restaurant, infinity pool and a private beach! This is more than a boat. It...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tee by the Sea - NO DAMAGE FROM HURRICANE IRMA , Plus 7 Bikes FREE1 / 30
    (67)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • DVD Player
    • Patio
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2017
    This lovely condo was great for our stay in Key West. Located on Stock Island just at the entry of Key West, it was perfect for staying "out of the frenzy" of town, but...
    Reviewed 13 May 2017
    We had a great three days on the island. Condo was well equipped although we ate out or got pizza - pizza place across the road served delicious pizzas. Ther were 5 of us so my...
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    About this property
    Very nice luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in very well maintained gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa with a 5' thick memory...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Botanical Island Delight C1201 / 45
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Washer
    • Sauna
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 January 2018
    It was a wonderful place to stay. We loved it. We had everything we needed. Was within walking distance to many things.. I definitely would stay there again
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    About this property
    This unit has a king in both bedrooms. 1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smathers Beach the City Beach with a variety of watersports activities available. The property itself features assigned secure parking spaces, 3 lighted tennis courts, one of which is...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families1 / 23
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 February 2018
    The Oasis is truly a bit of heaven on earth! We have been visiting Key West for a number of years and could not imagine staying anywhere else.This rental is fully equipped, in a...
    Reviewed 26 January 2018
    Recently spent 10 days at KWO. This property is superb and reflects a pride of ownership. KWO clearly exceeded the already impressive presentation on the website. Paula and...
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    PARKING,2bd/2bth,20yrd TO DUVAL,FREE OLD TOWN SHUTTLE,MAJOR ATTRACTIONS NEARBY1 / 41
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    • Patio
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2018
    Best part, it is right off of Duval and close to so many things to do. The beach is 5 minute walk and the community pool is an amazing unused gem. Free bus to lower Duval is...
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    About this property
    Check out the new 'Duval Loop' that ferries you around Old Town for free and is located at the corner of this homes block!!!!Map is included in pictures. Hemmingway House, Lighthouse, Butterfly World, Southern Most Point, Conch Tour Train, Beach, Galleries & Restaurants are all located within a 5...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Hammock - Comfortable 3 Bedroom Home1 / 15
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Terrace
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2018
    Thank you so much for the wonderful stay in your home Bob. We will defiantly stay here again if there is availability when we come. Everything from towels, beach towels, sand...
    Reviewed 27 March 2017
    Great times in key west coral hammock is about a fifteen minute drive to duval street. The place is real nice and quiet a lot of space for your whole group. Great trip all...
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    About this property
    This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Atlantic Paradise Found C2321 / 47
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
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    • Sauna
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 February 2018
    Great time in key west. The condo we rented was beautiful but, very pricey. We will look for a more economical option next time.
    Reviewed 9 September 2010
    The condo we stayed in had obviously been remodeled. It was gorgeous with plenty of space for 4 people! Also, the pool and jacuzzi were huge! We really enjoyed the accomodations...
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    About this property
    Atlantic Paradise Found C232 at 1800 Atlantic Condominiums is a beautifully appointed spacious condominium with a lovely view of the Atlantic Ocean Atlantic Paradise Found is one of the premium rental properties Condo's in the 1800 Atlantic Complex. Beautifully decorated with higher end...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations since I am not a real estate salesman or property manager allow me let the photos speak for themselves. My oversized two bedroom, one bathroom condominium is located on picturesque Southard...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Ocean Views
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    The Banyan Resort at Key West1 / 6
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Terrace
    • Internet Access
    • Outdoor Dining Area
    • Shared Garden
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
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    • Private Garden
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful, private home is located in a private, small subdivision with about 25 homes all on the open water, Gulf view. Its's a lovely home with 1 bedroom downstairs with a half bath and 2 large bedrooms upstairs with 2 full bathrooms. The master upstairs has a balcony with an exquisite view...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Grande Vista Penthouse on the Atlantic1 / 43
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Sauna
    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2017
    Beachfront condo, great pool, hot tub and grounds area. Poolside bathrooms have saunas, large rec room, library & a small gym that was a nice addition.Very secure with gated...
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    About this property
    The Grand Vista - 2 bedroom suite 2 Bedroom 2 bath suite, Totally renovated with flat screen plasma TV's in both bedrooms and the living room. All brand new furniture in Jan 2010, King bed in the Master bedroom, queen in the guest bedroom and a queen sleeper sofa in the living room. Full size...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
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    • Ocean Views
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    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2018
    Great location!!! They supplied many extras beach chairs and beach towels. Loved that they had bikes right at the condo. We would definitely book this condo again
    Reviewed 22 June 2017
    Great place to stay. Wonderful amenities! Would highly recommend. Location is great for beach, Mallory square and Duval Street.
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    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table and...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Key West Living-Oceanside Catamaran Esprit du Vent1 / 9
    (1)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 31 December 2017
    Nice boat, nice marina with ok restaurant and nice gym and pool. However note that boat is at Key West Yacht Club which is not actually in Key West. Located in Stock Island...
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    About this property
    Steps from the Ocean, Esprit du Vent is a spacious catamaran within minutes of Key West on Stock Island in a yacht club setting with a pool, beach and restaurant. The catamaran has 3 cabins, 1 head, and is bright, airy and spacious. Fully equipped with galley kitchen, oven, stove, coffee maker,...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Air Conditioning
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    • Sauna
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This wonderful property has brand new living and bedroom furniture in 2016, King bed in the master bedroom, 2 twins in the 2nd bedroom and a memory foam luxury queen sleeper in the living room will comfortably accommodate your party. Watch the sunrise from your private balcony. Enjoy the balmy...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Spectacular Atlantic Ocean View Condo (MONTHLY)1 / 26
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 May 2016
    When we arrived at the condo there was construction going on around it and it was a little confusing. However, when we got in the room it was breath taking !! The view is...
    Reviewed 27 December 2015
    This place was awesome. The pictures are not misleading. The balcony is right on the water, You are sitting on the porch with a morning cup of coffee and a great, unobstructed...
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    About this property
    ************************************************************************************************************************ NOTE: We are currently accepting only monthly rentals (28 days or longer). Please inquire for a quote....
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bimini Key West Penthouse C4241 / 39
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Private Outdoor Pool (Heated)
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    • Hot Tub
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2012
    We had an enjoyable experience from the time we arrived at 1800 Atlantic until we left. The nice security guard on duty on Sunday night couldn't have been more helpful. The...
    Reviewed 15 July 2010
    Every facet of our stay was perfect. We have stayed in many other places in Key West, and this is by far our favorite! We have stayed in this particular unit several times, and...
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    About this property
    Fantastic 1800 Atlantic Penthouse in the highly desirable East building of the facility 2 bedroom 2 bath top floor ocean-view condo at 1800 Atlantic. This unit has been totally renovated and no attention to detail spared, previously owned by the VP of Sony his taste was impeccable. The Master...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    A Touch of Bermuda in Key West1 / 19
    (17)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 October 2017
    By the time you arrive, you will already feel like you are part of Jack's family. He will literally bend over backward to accommodate you. We have vacationed in Key West for...
    Reviewed 14 July 2017
    I stayed in Jack's condo (a touch of Cuba in Key West) this past week and we enjoyed every aspect of it. The condo is two bedroom one bath and was perfect for my party of three...
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    About this property
    Envision yourself unwinding and getting into the casual clothes we wear in Key West while you look around and know you are in Paradise as our island is called. Then ask anyone and they will tell you the best place to stay in Key West is the Truman Annex. My Bermuda-style cottage is just past the...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Casita1 / 24
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Terrace
    • Grill
    • Balcony
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2017
    We stayed at Coral Casita for two weeks with our extended family. We were very happy with the rental accommodation from start to finish. The property was very clean and well...
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    About this property
    Coral Casita - Weekly Vacation Rental Completely re-designed, re-decorated and ready for your island adventures! When Key West is calling your name and nothing else will do, Coral Casita is the perfect mix of location, price and room for your large group to gather. A spacious 3 bedroom...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Anchor Drop Key West A3071 / 55
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Washer
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    • Sauna
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 December 2017
    The condo was exactly as it was pictured. Love the way the balcony was accessible from the living room or the bedrooms. I absolutely fell in love with the shower. The owners...
    Reviewed 15 July 2015
    We really enjoyed our stay. The condo was very spacious, clean and updated. It was far more comfortable than a cramped hotel room and actually cost less. We were there for...
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    About this property
    Anchor Drop A307 is a totally renovated top of the the line unit. King bed in the master bedroom, 2 twins in the guest bedroom and a queen sleeper sofa in the living room. Anchor Drop is beautifully renovated and decorated by an interior designer. Custom bathrooms and modern kitchen with...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    LAST MINUTE DISCOUNT! 48' Sailing Yacht. Other Yachts & Boats Available!1 / 31
    (29)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 May 2018
    The best AirBnB experience I’ve had! This yacht was a dream come true! I imagined everything I wanted for my bachelor party and medical school graduation and found it on this...
    Reviewed 24 April 2018
    Such a cool, unique experience! Anyone can go to Key West... But staying on a boat like this really sets the trip apart. Everything in this listing is spot-on. Here is a pretty...
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    About this property
    Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class marinas giving you full access to its restaurant and private pool during your stay. The marina is located close to...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Garden Oasis is a first floor condo in the Shipyard Condos in Truman Annex. We are ideally located 2 blocks from the action (restaurants, shops, clubs) of Duval St., and very short walks to sunsets at Mallory Sq, and the beaches of Ft. Zachary Tayler Park. The Shipyard is a lushly landscaped...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (55)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
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    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2018
    This is either the second or third time we've stayed here so that should tell you its quality. Beautiful condo with everything you need for a comfortable home away from home...
    Reviewed 26 May 2018
    Joanne and Jim were very nice and helpful! I loved the house and the location is superb! Beautifully furnished and comfortable. My only concern was the lack of hot water in...
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Penthouse property with vaulted ceilings at the famous 1800 Atlantic. Both bedrooms and the living room have access to your private balcony with great views of the property and Atlantic Ocean. The Owners are fishing enthusiasts as you will see when you relax in the comforts of home away from home....
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6 This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is a...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Truman Annex Irish Condo Innisfree1 / 33
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • DVD Player
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2016
    This was my 2nd time staying in the Shipyard section of the Truman Annex. Each time was in a different 2BR condo. this condo was clean, well equipped with kitchen, bath...
    Reviewed 24 January 2016
    I attended college at a later age and upon graduation took 2 friends and my sister to Truman Annex for a 10 day vacation!!! We had the best time. As a matter of fact I am back...
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    About this property
    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Downtown Nassau Oasis 1 Bedroom Townhouse steps to Duval1 / 22
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    • Balcony
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2015
    My (adult) daughter and I drove down to Key West for 4 days/nights - I had only been there once; she had never been there. We are from the midwest - it was hard to choose a...
    Reviewed 18 August 2014
    This small townhouse was absolutely the most convenient thing we could have asked for in Key West. 1/2 block off Duval Street at Truman. We literally parked the car and walked...
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    About this property
    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Real World MTV House Key West1 / 247
    (49)Very good
    10 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    • Waterfront
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 October 2017
    This house was really cool rooms were spacious and massive , the master room was so lavish . Jacuzzi in living room was a great feature and the games room . Only downside was it...
    Reviewed 29 March 2017
    What would you expect when you first see this colorful place? Party?Well, you might bring your group here and party all night long. Or you can take them here to have an...
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    About this property
    THIS ISN'T JUST A HOUSE, THIS IS YOUR OWN PRIVATE MINI RESORT IN KEY WEST, FLORIDA. THIS IS THE PROPERTY USED BY MTV TO FILM THE 2006 REAL WORLD KEY WEST. 500 FEET OF OCEANFRONT, 8 to 10 BEDROOMS are available (sleeps up to 20) , 5 1/2 baths, 11 plasma TVs, pool table (and Ping Pong), tennis...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 10 Bedrooms, 6 Bathrooms, Sleeps 22
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Parking
    • Private Outdoor Pool (Heated)
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    KOKOMO (monthly rental): Everybody knows a little place like Kokomo. Now if you want to go and get away from it all go down to Kokomo. Tropical drinks melting in your hand, we'll be falling in love to the rhythm of a steel drum band down in Kokomo. It's not Bermuda or the Bahamas but better, a...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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