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Holiday Rentals near Key West Intl Airport

3491 S Roosevelt Blvd, Key West, Florida 33040
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 25 Rentals in Key West
    Key West Beachfront Luxury 2/2 Condo  A212 No Hurricane Damage1 / 38
    (43)Excellent
    1.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Top floor, two bedroom,two bath condo with private balcony,close to the Ocean1 / 47
    (4)Excellent
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Oceanfront 2 Bedroom 2 Bath Condo Key West Florida1 / 34
    (14)Excellent
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Welcome Aboard!  Relax, unwind, enjoy the water! in key west1 / 50
    (2)Excellent
    0.4 kilometres from Key West Intl Airport
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 July 2018
    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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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    Ocean Vista1 / 13
    (1)Excellent
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Terrace
    • Ocean Views
    • Sauna
    • Hot Tub
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 January 2021
    We had an excellent time here! Not only was checking in easy, but the place was equipped with hand sanitizer on the wall and in the guest binder was a note from the cleaners...
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    About this property
    Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flair. Full kitchen with all...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps to the Beach and Sunrise Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnished with all of the comforts of home. Large flat screen tv, ensuite bath, full laundry center, fully stocked kitchen, assigned parking bay and...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2.1 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Waterfront
    • Patio
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southern Crosser is the latest luxuriously designed cruising catamaran from world renowned French boat builder Fountaine Pajot. ​Following her initial voyage from France to Ft. Lauderdale for commissioning, she was delivered to her new Key West home in January 2018. This brand new vessel is 3.85...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    1.9 kilometres from Key West Intl Airport
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. La Brisa is a two bedroom two bath condo on the third floor. The master bedroom has a king size bed with a walk in closet, a desk...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.3 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Washer
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private home located in New Town available for 4 week minimum rental. Beautifully landscaped yard with secure private back yard and pool. Use of bicycles and four passenger electric car provide flexible transportation all over the island. The home features a modern kitchen with all appliances...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Seaside Condo 2 pools. sunny, quiet, near Old Town1 / 17
    (2)Excellent
    1.5 kilometres from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Secure Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2016
    This apartment was the perfect place to experience Key West, it was sunny and quiet, right across the street from the beach and just minutes away to Old Town with it's great...
    Reviewed 12 March 2016
    This Key West getaway condo is a wonderful escape from the freezing temperatures of the northeast. I was here other years and noticed this time that there is a beautiful new...
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    About this property
    This delightful sunny, quiet apartment is located across the street from Smathers beach and just a ten minute drive to Old Town. The apartment is set in a large lush tropical garden with two Olympic size swimming tools, tennis court, shuffle board court and outdoor lounging and dining areas, It is...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Henry's Piece Of Paradise On The Ocean In Key West1 / 20
    (36)Excellent
    1.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Hot Tub
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2018
    We stayed 5 nights. It was even better than I anticipated. The condo was secure with private parking. The kitchen had everything we needed. Loved the Key West color scheme in...
    Reviewed 4 March 2018
    Henry's Piece of Paradise is just that. Beautiful condo w lovely furnishings, created w whimsy & color. Comfortable and well equipped kitchen & large balcony. The pool...
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    About this property
    Key West Vacation Rentals 2 Bed 2 Bath Condo On The Ocean with partial ocean views - rent weekly or nightly. Thirteen-hundred-fifty square feet of fabulous living space located on the second floor with garden and partial ocean views from a 38-foot private balcony accessible from the living and...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    1.3 kilometres from Key West Intl Airport
    8 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Air Conditioning
    • Private Garden
    • Parking
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In 1926, one of the richest men in South Florida, his family owned 45 percent of the land in Key West and most all of the shrimp and fishing boats in the Keys, married a beautiful young New York socialite and wanted her to move to Key West to live with him. 'Honey', I will only move to Key West if...
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    Key West, Florida Keys
    Holiday Rental House - 8 Bedrooms, 8 Bathrooms, Sleeps 20
    2.2 kilometres from Key West Intl Airport
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Housekeeping Included
    • Grill
    • Hot Tub
    • DVD Player
    • Ocean Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    80 foot yacht with a crew of three, Captain, first mate and chef. There are 3 staterooms all with ensuite baths. The master has king bed and double baths w/ a connecting shower between .Second bedroom has a queen bed and the third has 2 twins - -convertible to a large queen . Luxury yet...
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    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
    0.6 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Parking
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An ideal choice for your coastal getaway, this waterfront 3BR/2BA home on Big Coppitt Key is situated on a canal with a floating dock, perfect for days of boating and sunbathing. The interior offers an updated kitchen, two TVs, and canal views. LIVING AREA Kick back and watch a movie on the TV in...
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    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Private Outdoor Pool (Unheated)
    • Grill
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bask in complete privacy in this Key West tropical paradise with a lagoon style pool. This property is pet friendly. Flagler's Oasis is a two-bedroom, recently renovated private home with a brand-new kitchen with granite countertops, stainless-steel appliances, beautiful hardwood floors, and a...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Island Hideaway1 / 22
    (1)Excellent
    0.8 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    The condo was so cute and perfect! Miriam was very helpful and has excellent communication. I would highly recommend staying here. We had two bedrooms and two bath, nice...
    Reviewed 10 May 2021
    Miriam was an amazing host and great communication! This home was perfect for our stay and this location is close to everything.
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    About this property
    Welcome to Island Hideaway located in beautiful Sunrise Suites Resort. Come relax by the lagoon-shaped pool surrounded by lush tropical foliage overlooking a Salt Ponds Preserve, grill your fresh catch downstairs using the community BBQ grills, enjoy a sunset tennis match with your partner or break...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.9 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Salt Ponds Sanctuary! This beautifully adorned condo on the third floor of the Salt Ponds Condominium Complex in Key West boasts a private balcony to view the sunset while sipping your favorite cocktail. You are minutes from Duval Street where you can sample the many restaurants and...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    1.9 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Grill
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Atlantic Ocean is just at your reach when staying at Papaya Place! You can almost hear the waves of the ocean! This great 2 bedroom, 2 bath, waterfront Key West condo at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve. Enjoy the peace and...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy spectacular ocean views from this lovely rental! This two bedroom, two bath condominium is located oceanfront in a gated community with a direct view of the Atlantic Ocean. Enjoy amazing views from this waterfront rental condo of the sparkling blue-green waters from your private balcony...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2.3 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to a golfer’s paradise at Spa Oasis! Located in the Sanctuary of the gated and exclusive Key West Golf Club, this spacious single-family home welcomes you to the laid-back island life with the ease of everything on one floor. You and your guests will enjoy being close to the best that Key...
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    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.5 kilometres from Key West Intl Airport
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • DVD Player
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Coconut Mallory #411 This beautiful condo is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina with boat dockage (additional fee), as well as, one of the locals' favorite...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.9 kilometres from Key West Intl Airport
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
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    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Lotus Blossom! This tropical home is located in Key West. This private retreat offers peaceful tranquility while still close enough to enjoy the action of Duval Street! The tropically landscaped courtyard boasts a hot tub and plenty of seating to relax and enjoy your morning coffee and...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.7 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An exceptional stay awaits at this 2BR/2BA vacation home. Highlights include a Resort-style community pool with chaises, cabana, clubhouse, and tennis courts. Picnic area with BBQs for cookout gatherings. You'll love being located in Key West. THE TURNKEY PROMISE With TurnKey, you’ll always find...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.9 kilometres from Key West Intl Airport
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Balcony
    • Washer
    • Sauna
    • Internet Access
    • Grill
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautifully renovated high end luxurious monthly rental at 1800 Atlantic. The moment you walk in you will appreciate the attention to detail. Enjoy the lovely views of the complex and Atlantic ocean from the private balcony. The master bedroom suite has a king size bed. The renovated...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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