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Holiday Rentals with Pools in Matecumbe Key

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    Travellers to Matecumbe Key are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    191 Matching Rentals in the Matecumbe Key AreaView all 324 rentals
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    75731 Overseas Highway1 / 32
    (13)Very good
    Matecumbe Key
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Private Beachfront Paradise1 / 45
    (12)Very good
    Matecumbe Key
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Matecumbe Key
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Matecumbe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this...
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    33036, Matecumbe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Matecumbe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relaxation at its best awaits you in our beautiful, Keys townhome on mile marker 87. Executive Bay Club is located in Islamorada, the Sports Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a heated swimming pool, a clubhouse, a private beach...
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    33036, Matecumbe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Matecumbe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Grill
    • Hot Tub
    • Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. 'Beacon Reef 406' is an excellent choice for your vacation getaway, whether you're planning on staying a month or the entire season, this is a great unit. Beacon Reef is centrally located in the Heart of Islamorada making it convenient to...
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    33036, Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Matecumbe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Hot Tub
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 28 Days NEW ON THE RENTAL MARKET. 'Beacon Reef 522' offers magnificent 180 degree oceanfront views. Enjoy the sea breezes as your relax on your private balcony and gaze at the water. Whether staying one month or more you will be more than happy with your choice to stay here....
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    33036, Matecumbe Key, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Matecumbe Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Washer
    • Grill
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come and relax at our beautiful town home in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a fishing/boat dock. This...
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    33036, Matecumbe Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Matecumbe Key
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 1 bedroom/1 bath condominium is located in Summer Sea in Tavernier. This is a gated complex located directly on the Florida Bay at Mile Marker 88.5, which is within the Village of Islamorada. The unit has a stunning view of the bay from the living room, master bedroom and the balcony. It...
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    Location Information
    33036, Matecumbe Key, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    The following rentals are within 10 kilometres of Matecumbe Key.
    Oceanfront Condo - Pool, Beach, Tennis & Marina1 / 28
    (9)Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Washer
    • Waterfront
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 April 2018
    This condo was a perfect home base for our family to explore the Keys. The pool was beautiful and there was new landscaping across the condo complex. Craig (the owner) was...
    Reviewed 12 August 2017
    We are a fam of 4 with two teen boys and we found the condo perfect for us as a base for our trip to Key Largo. It has everything you need, is close to groc. stores...
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    About this property
    April, 2018 Update! We have now completed many upgrades and look forward to hosting your stay in the Florida Keys. Our beautiful, 2/2 condominium located is directly on the ocean in Key Largo (Tavernier), Florida. As this is 4th floor 'END' unit there are many windows that provide an open,...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean pointe  island retreat1 / 23
    (6)Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2017
    Ocean pointe is just to the south of Ke Largo and only an hour and a half to two hours from Key West. The retreat itself has good security with each car stopped at the gate on...
    Reviewed 25 March 2017
    This is a very nice condo and very adequate for 4 people although you can't get more than 2 people on the balcony at one time. It is pretty small but does look right out at the...
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    About this property
    The newly renovated oceanfront condo is located in Tavernier Key, a community situated along the southern border to Key Largo. The grounds encompass over 60 acres and is situated in a tropical paradise surrounded by mangrove forest, coconut trees and the pristine turquoise waters of the Florida...
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    33070 3100, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Ocean View Penthouse1 / 7
    (18)Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2018
    We was a family of 5 staying in this condo & was worried it would be a squeeze to fit us all in but I didn’t need to worry as the condo is very spacious.Lovely kitchen area...
    Reviewed 6 July 2018
    Beautiful clean condo with a great ocean view. Centrally located to many restaurants and shops. Joe answered all of our questions promptly and texted us periodically to see if...
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    About this property
    This totally updated condo features full ocean views from almost every room. Watch the sun rise from the balcony as you enjoy your morning coffee. Enjoy an evening cocktail out on the jetty. Take it easy by the pool or enjoy the water sports and fine local seafood restaurants in the area. The...
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    33037, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Come relax in Islamorada, the tropical jewel of the Florida Keys!!1 / 9
    (3)Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Private Garden
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 June 2018
    It was perfect! Super clean, tasteful, & just the right size for what I needed! I absolutely loved it & would definitely stay again!!
    Reviewed 6 March 2018
    Tastefully decorated and very neat and clean. Comfortable throughout, beautiful setting & perfect to relax & get away from it all!!
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    About this property
    Beautiful 1 BDRM apartment located in Islamorada. Full kitchen and 1 full bath. Home is located on canal within 100 yards of the ocean. You will enjoy access to fully screened and heated pool. WiFi and cable TV included. Close proximity to shopping, restaurants and all the best the Keys have to...
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    Location Information
    33070, Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Large Townhouse in Mariner's Club Resort - 3 BR/3.5 Bath1 / 26
    (5)Very good
    Tavernier
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Children's Pool
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    My family and a couple of close friends spend Thanksgiving weekend here. The layout was perfect for us. The first floor has a master bedroom, kitchenette, and a small living...
    Reviewed 26 August 2018
    Every year near the end of summer, I plan a Keys vacation. It did not matter which part of the Keys my family and I would visit. I know this would break the bank vacation. After...
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    About this property
    There is room for the whole family in this 2,200 sq. ft. townhouse with In-Laws quarters. As you enter the first floor you will find an open floor plan with living room, full bathroom and kitchenette with microwave, toaster, coffee maker, portable induction single-burner cooktop, and refrigerator....
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    33037, Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    OCEANFRONT CONDO WITH ALL AMMENITIES!1 / 85
    (22)Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Waterfront
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 September 2018
    The info provided by the owner was right on the nose. The condo was clean and well maintained. The pool was very nice and clean. The beach had a little to much seaweed for me...
    Reviewed 9 July 2018
    My family stayed the 4th of July week. The community is very safe and clean with great amenities. Pool is large with plenty of room for the residents. It’s a great location that...
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    About this property
    Ocean Pointe Suites is located directly on the Atlantic Ocean. This unit is completely renovated and is located in building 4 which is the most desirable building. Featuring magnificent ocean views from the living room, master bedroom and porch. This unit offers 1 King bed in master bedroom, 1...
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    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tarpon Cove at Ocean Pointe Resort1 / 17
    (3)Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Waterfront
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 August 2018
    We stay from July 28 to August 10 , the apartment is outstanding, great pool . If you have a boat the marina is very good ,will be back next year for sure.thanks
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    About this property
    Take a trip to the Fabulous Florida Keys and stay at Tarpon Cove at OCEAN POINTE RESORT CONDOS, a private 65 acre tropical resort. Our totally renovated 2 bedroom/ 2 bath beautifully furnished apartment. Sleeps 6 and is ready for you and your family. Tropical landscaping, sandy oceanfront beach,...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    FLORIDA KEYS OASIS # The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 31
    (5)Excellent
    Islamorada
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Ocean Views
    • Patio
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2018
    Despite our rainy week in Islandmorada, Sean helded to make our vacation seemless! We had 10 people staying with us to help celebrate my husbands 50th birthday. The house had...
    Reviewed 13 July 2017
    The property manager was super helpful and walked us through the entire house showing us all the nooks and crannies. I must say I've never had someone take close to 45-an hr to...
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    About this property
    ***7 day minimum rental - notwithstanding anything in the rates page the MINIMUM rental is 7 days ****This custom built 5 bedroom house has been immaculately taken care of and has a proper size elevator and is fully wheel chair accessible. Enjoy your stay in Sereni-key looking out to an endless...
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    33036, Islamorada, Florida Keys
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    All NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!1 / 31
    (3)Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 September 2018
    Simply an amazing condo. Location was perfect, made a great trip AMAZING. Owner was very accessible and friendly. Sunrise and set, along with the full moon views , just...
    Reviewed 28 April 2018
    Totally renevated condo with gorgeous views of ocean It was so nice to stay here! So cozyNice pool area! Co-owners were very friendly and made you feel at “home”Condo...
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    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. And new this year, a sandy beach. For two couples or a family with 2 kids. The two new extra long twin Pillow Top beds in 2nd bedroom convert to a comfy King Bed! Master bedroom has new Simmons Beautyrest Pillow Top...
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    33070, Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    **Winter Promo**  Modern Executive Bay Club Condo with Pool & Beach1 / 29
    (3)Very good
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Terrace
    • Wi-Fi
    • Grill
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2015
    Our townhouse was clean, spacious, & quiet. Lovely updated kitchen and laundry. The pool was delightful, and the beach & dock were very enjoyable as well. Very peaceful...
    Reviewed 28 March 2015
    I really enjoyed my stay! The place was great. I loved the layout. Very roomy. Enough space for everyone. The pool was great and even played a little tennis.
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Come and relax at our beautiful town home on...
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    Location Information
    33036, Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Islamorada
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for an amazing home in Venetian Shores?  This home has everything - 4 bedroom, 4 bath home that has been updated.  The kitchen is amazing, suited for any type of entertaining.  The 3rd floor floor is a lofted master bedroom suite with a walk-in closet.  Two guest bedrooms are located on the...
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    33036, Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    No dockage allowed. Florida Keys. Beautiful condo. Short walk to the beach area.1 / 18
    (7)Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2016
    This was our first trip to Florida, it was agreed that we would leave Orlando and the parks for a few years as our children are still quite young (4 and 1). We did extensive...
    Reviewed 18 January 2016
    We had very nice time staying in Ana's townhouse in Islamorada. It is nicely decorated, well equipped, comfortable and spotlessly clean. There is more than enough room for a...
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    About this property
    Our unit is a short walk to the beach and dock... No view of the ocean from our unit. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Bay Front Beauty/ Summer Sea Must See!!!!1 / 19
    (4)Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Ocean Views
    • Children's Pool
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    Everything was perfect. Weather was great, the unit was clean and fully furnished with everything we needed. The other vacationers and full-time residents were friendly and...
    Reviewed 5 May 2016
    This condo was to die for. The decor was fabulous and the location was perfect and close to many restaurants. The sunset from the balcony was breathtaking. The owner was a...
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    About this property
    Beautiful / tropical decorated one bedroom, one bath water front condo in Summer Sea Condominiums located at Mile Marker 88.5 Bayside Islamorada, FL. Bayside means amazing open water views & world famous Florida Keys sunsets from your own private balcony overlooking the Florida Bay. You can also...
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    Location Information
    33070, Islamorada, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Luxury 3 BR condo, boatslip, easy accces to ocean1 / 19
    (5)Excellent
    Islamorada
    3 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Air Conditioning
    • Ocean Views
    • Patio
    • Washer
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 June 2017
    We thoroughly enjoyed our stay in this beautiful, luxurious condo. It's roomy and clean and has all the amenities you could possibly want. I only wish we could've stayed longer...
    Reviewed 24 November 2016
    very neat and clean. Great location and views. Easy access to all of the Keys. Spacious nice size kitchen for cooking a meal if you feel like it. Nice location, because it's far...
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    About this property
    Luxurious end unit in Bay Harbour with a boat slip. Upon entering the unit you are greeted with the tranquil views of the harbor and ocean. Enjoy the ocean breeze from the large screen porch. Beautiful Bay Harbour gated condo community on lower Matecumbe, mm 74 1/2. Enjoy the sunrise or sunset...
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    Location Information
    33036, Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 6 Bathrooms, Sleeps 8
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    ISLAND STAY 2BR/2BA SUITE, PRIVATE BEACH, POOL, TENNIS COURTS, CAFE, KITCHEN1 / 35
    (1)Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Housekeeping Included
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Found it!! Get ready for the ultimate Florida Keys vacation! If Florida is a state apart from the USA, the Keys are the islands apart from Florida - in other words, it’s different down here. Enjoy sun-kissed beaches lapped by aquamarine waters, the only Coral Reef in the continental US and water...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    OCEAN VIEWS ALL ROOMS ! TOP FLOOR LARGEST CONDO1 / 128
    (24)Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2018
    Absolutely wonderful, with all facilities and views of the ocean from most rooms. Pool just across the way.Tony (owner) was thoughtful and considerate checking all was ok for...
    Reviewed 12 August 2017
    The condo is wonderful - the beach is on the doorstep and the view from all the windows is amazing! It is a great family-friendly condo with a great pool area, the area is super...
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    About this property
    We received Trip Advisor's 2017 & 2018 Certificate of Excellence 'Best Condo in the Keys' award! Its all about being tastefully decorated, on the top floor of the best building with the largest end unit with ocean views from all 12 windows. See a UTube walk through video of our condo: Go to...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Washer
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom and 2.5 Bath Villa, in Anglers Reef. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard terrace with barbecue, front porch seating, balcony, and dock....
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    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    THIS IS IT! Magnificent Oceanfront Paradise!  WE ARE OPEN!!1 / 17
    (5)Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Ocean Views
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 July 2018
    Great vacation. Received the much needed peace/quiet for rest that was well overdue. Room clean and relaxing. Visited Key West for a day trip while here and had a great time...
    Reviewed 2 June 2018
    The condo was fantastic, clean and with great facilities. The pool was excellent and fellow guest very friendly. The owner was in touch throughout our stay and could not have...
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    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 2-5 people. , large pool on the ocean, . many water-front restaurants and bars nearby. Oceanfront mm 90, Plantation Key. Books up very quickly. Reserve early! Note: We are licensed in Islamorada:...
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    Location Information
    33070, Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    FALL SPECIAL DISCOUNTED PRICING!!!1 / 70
    (17)Very good
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Balcony
    • Terrace
    • Outdoor Dining Area
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 May 2018
    We recently rented this condo unit for a week for our family of six. It accommodated us great, 3 bedrooms plus a pull out couch. Outside was beautiful, very clean and well...
    Reviewed 13 March 2018
    Love staying in this condo was our second year hoping to return next winter if available. already made request.. I would never leave if it were up to me but the location and the...
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    About this property
    Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, and dockage for...
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    Location Information
    33070, Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fabulous 6 Bedrooms /4 Bathrooms Tropical Waterfront Pool Home!1 / 15
    (1)Excellent
    Islamorada
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    We are one of two couples who each have rented a level for the past six winter seasons and we are so looking forward to returning in 2018. The location is perfect-within one...
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    About this property
    Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. Video of house and area available upon request. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. Our beautiful home is Great...
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    33070, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Pointe Suites in Tavernier mile marker 92, is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. From sunrise to sunset you can enjoy the many activities our...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    STUNNING 2 BEDROOM OCEANFRONT SUITE WITH MAGNIFICENT VIEWS1 / 23
    (1)Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Ocean Views
    • Air Conditioning
    • Grill
    • Waterfront
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 November 2016
    I booked this condo as a surprise for my husbands birthday and it was perfect, my only complaint is that i wish we would have made our stay longer! It was an hour and a half...
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    About this property
    Ocean Pointe Suites is located directly on the Atlantic Ocean, and is one of the finest destinations in the Florida Keys. This unit is located in building 3 which is a desirable building. Featuring magnificent ocean views from the living room, kitchen, master bedroom and 2 porches. This unit offers...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Ocean Views
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    WE OFFER 10% OFF TO ALL MILITARY, FIRST RESPONDERS, AND TEACHERS. PLEASE MESSAGE US BEFORE BOOKING SO WE CAN APPLY YOUR DISCOUNT! THANK YOU FOR YOUR SERVICE! Newly renovated ocean view condo in beautiful Tavernier, FL! Ideally situated in the Upper Keys, between Miami and Key West, this condo is...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Tropical 2 Bedroom Ocean View Suites - Minuets Away from World Class Fishing, Di1 / 66
    (17)Average
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2016
    With nearly 2,000 reviews, the Trip Advisor average rating of 3.5 is spot-on. If given that as a choice, that's what I'd give it.We stayed at Ocean Pointe six nights during...
    Reviewed 25 February 2016
    we had a great stay! the condo had plenty of room 2bed/2bath including a washer and dryer in the unit. We got there late and have no troubles finding it and the cheque in at the...
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    About this property
    Ocean Pointe Suites in Tavernier mile marker 92, is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. From sunrise to sunset you can enjoy the many activities our...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE KING MASTER BEDROOM IS DRESSED IN ISLAND FINERY WITH PRIVATE BATHROOM, COMBINATION SHOWER/TUB, AND FLAT SCREEN TV MAKES FOR THE PERFECT RETREAT. THE SECOND BEDROOM OFFERS A QUEEN SIZE BED, A FLAT SCREEN TV, AND AN ATTACHED BATHROOM. YOU CAN “COOK YOUR CATCH” IN THE FULLY EQUIPPED KITCHEN WITH...
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    Location Information
    33036, Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Venetian Tropics 3 bedroom pool home on sailboat canal weekly vacation rental1 / 38
    (28)Excellent
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Washer
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2016
    Over the years, we have stayed here 4 times, and each time gets better due to the improvements to the property. The location is perfect and relaxing for folks who like to fish...
    Reviewed 28 March 2016
    This is my fourth year at the property and it has only gotten better. There were some criticism of the deck conditions and lack of refrigerator at the outside Tiki hut. Those...
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    About this property
    Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email me for the application. Weekly vacation rental...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Oceanfront 2 Bedroom/2 Bathroom Well Maintained Condo with Large Balcony1 / 14
    (7)Very good
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 November 2018
    This was our first visit to the Keys. Although the area has mostly recovered from the hurricane, there were still a number of construction projects in progress. The condo was...
    Reviewed 20 October 2018
    Beautiful view from the 3rd floor. Located away from US1 traffic so very quiet. Centrally located between Islamorada and Key Largo.
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    About this property
    This condo has been completely restored after Hurricane Irma’s d is now ready for guests to return. There is new drywall, paint, carpets and new furniture and is safe to stay in. Paradise by the Atlantic Ocean and only 50' front the waters edge. Beautiful condominium complex with heated out door...
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    Location Information
    33070, Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Moon Bay A2041 / 33
    (1)Very good
    Tavernier
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 March 2018
    This condo was a perfect location for our vacation. Restaurants, shopping and parks close by. The most beautiful sunsets I have ever seen.
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    About this property
    Want to be close to the Mainland while still being in the Upper Keys? Look no further. This beautifully decorated condo at Moon Bay will not disappoint. The Master bedroom has a spacious King size bed. Guest bedroom has 2 twin beds and there is a bonus room with a trundle bed. Vibrant colors...
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    Location Information
    33037, Tavernier, Key Largo
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Patio
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
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    Location Information
    33036, Islamorada, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Pointe Suites in Tavernier mile marker 92, is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. From sunrise to sunset you can enjoy the many activities our...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Pointe Suites in Tavernier mile marker 92, is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. From sunrise to sunset you can enjoy the many activities our...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Enjoy the Florida Keys!1 / 33
    (5)Very good
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Sauna
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Balcony
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 February 2016
    Very relaxing, friendly environment, with an excellent view of the ocean, we had a great time during our stay.The owner "Tad" was very helpful, whenever we had questions...
    Reviewed 1 February 2016
    The location is in a very good position and permit to visit all the most important site of Keys, Everglades and Miami in a daily tour.The set up of the apartment is complete and...
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    About this property
    VILLAGE OF ISLAMORADA REQUIRES MINIMUM OF 29 NIGHT STAY Come enjoy our home away from home. Perfect for a couples retreat. Enjoy your own fully equipped condo. Sip coffee on the balcony and watch the beautiful sunrise. Read one of our Jimmy Buffett books and dream of running away for a life on...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Tavernier
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Well appointed & spacious.3-level licensed Vacation Rental condo in t Kawama Yacht Club, a gated resort with 24x7 security on the Atlantic Ocean! Great exposure & beautiful sunsets. Separate private laundry room in the condo! Pools and lagoon Boasting an outdoor 2 swimming pools, Kawama Yacht Club...
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    Location Information
    33037, Tavernier, Key Largo
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedroom Tropical Partial Ocean View Suites- Pool, Dock & Marina - Near all Maj1 / 22
    (1)Very good
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Hot Tub
    • Washer
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    The location is great - the amenities are great - the pool very nice. These units are owned by individuals so be aware that not all units are up to par. The first two bedroom...
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    About this property
    Ocean Pointe Suites in Tavernier mile marker 92, is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. From sunrise to sunset you can enjoy the many activities our...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Pointe Suites in Tavernier mile marker 92, is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. From sunrise to sunset you can enjoy the many activities our...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury condo overlooking harbor with ocean view1 / 20
    (6)Excellent
    Islamorada
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Washer
    • Waterfront
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2018
    Luxurious surroundings, plush bath towels, great view, modern everything, cold central A/C, great soft pillow-top bed & nice quality linens. And, did I mention the...
    Reviewed 4 April 2018
    We are avid lovers of the keys and returned to vacation here about 20 times. We have stayed at Bay Harbor 3 times, but this condo is really superior. First, Lee is an...
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    About this property
    This premier luxury home is situated in a very quiet and peaceful gated community. All the rooms are very spacious with quality furnishings. A large double wide lanai with breathtaking views will make your getaway in the Keys. For your enjoyment it comes with private boat dockage, covered parking,...
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    Location Information
    33036, Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    **Winter Promo** Spacious Condo in Futura Yacht Club w/Pool, Tennis, Marina; Bri1 / 25
    (1)Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Grill
    • Balcony
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 August 2016
    My husband and I love the Florida Keys and this condo made our stay very enjoyable. Everything was very clean, organized and modern. It has the perfect feel of a Florida Keys...
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Futura Yacht Club is located in the Upper...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Washer
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Pointe Suites in Tavernier mile marker 92, is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. From sunrise to sunset you can enjoy the many activities our...
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    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tavernier
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Patio
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Owner is highly motivated to rent! Contact us to inquire about your stay *** Live like a local at this private oasis on mile marker 103 in the Keys. Enjoy your private pool and private beach, or soak up the rays on your own sandy sun deck, while overlooking the vast ocean views. John Pennekamp...
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    Location Information
    33037, Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Pointe Suites in Tavernier mile marker 92, is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. From sunrise to sunset you can enjoy the many activities our...
    View all property information
    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Grill
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ocean Pointe Suites in Tavernier mile marker 92, is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private road and gatehouse. From sunrise to sunset you can enjoy the many activities our...
    View all property information
    Location Information
    33070, Tavernier, Key Largo
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
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