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Holiday Rentals with Pools in Florida Keys, FL

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    1 / 17
    4.5 of 5 bubbles (33) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 14
    4.5 of 5 bubbles (37) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 23
    5 of 5 bubbles (4) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 17
    5 of 5 bubbles (15) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 1 week ago
    Best location, price, and amenities with simplistic booking,..will definitely return to The Key West Bahama House!
    3 of 5 bubbles Reviewed 1 February 2017
    Walking distance to Duval but on a quiet street. Arrival and departure procedures were simple. The parking situation isn't the best, but we weren't bothered by it since we like to...
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    1 / 39
    5 of 5 bubbles (36) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Waterfront
    • Air Conditioning
    • Sauna
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    • Hot Tub
    • Satellite TV
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    • Pet-friendly
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    • x
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    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 22 November 2016
    We were so thrilled to stay in this vacation rental, My mom is in a wheelchair full time and there was enough room for her to get around, the bathroom was perfect for her. My 2...
    5 of 5 bubbles Reviewed 6 August 2016
    Best aspect: owner Kathy W. communicated as stay got closer. She even asked how we were doing the day of travel and invited us to call her with any concerns or questions. We...
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    1 / 17
    5 of 5 bubbles (15) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Waterfront
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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... View all property information
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 bubbles Reviewed 31 August 2016
    The property manager was very helpful. The property was recently remodeled and very clean. It was spacious enough for two couples. Two bathrooms were ideal since there were two...
    5 of 5 bubbles Reviewed 17 August 2015
    The apt. Was beautiful in an awesome location. Close to shopping areas. Marina was great. Fishing was awesome. There were lots of people diving. Lots to do too little time...
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    1 / 30
    5 of 5 bubbles (7) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Satellite TV
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    • Hot Tub
    • Waterfront
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2,000 square feet on 2 levels with under cover parking. It is located in the... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 bubbles Reviewed 27 July 2016
    I stayed in this condo for a week with my 3 children (ages 12, 19, and 20) and a friend and her child (age 20). The condo was located near all that we wanted to explore in...
    5 of 5 bubbles Reviewed 23 November 2014
    Really enjoyed this home, clean,secure, owner answered all questions in a timely fashion. Highly recommended!
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    1 / 21
    5 of 5 bubbles (5) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Washer
    • Waterfront
    • Ocean Views
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    We are offering for rent our beautiful, 2/2 condominium located directly on the ocean in Key Largo (Tavernier), Florida. As this is 4th floor "END" unit there are many windows that provide an open, bright feel and offer views of the ocean throughout. Our location provides direct ocean access in... View all property information
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 bubbles Reviewed 16 February 2017
    We have been renting this condo for 12 years. We are extremely happy with this condo. The condo has everything you need whether it be for a week or a month. The condo is very...
    5 of 5 bubbles Reviewed 24 October 2016
    The Condo was Excellent, and we had a great time . The pool and hot tub were very refreshing,The water was so clear we could not bleive it
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    1 / 96
    5 of 5 bubbles (11) Excellent
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Satellite TV
    • Patio
    • Waterfront
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Key Colony Beach house (duplex) description SPECIAL rate of $1100 for 4 guests (may have 6) $10 per extra person per day, 6 max total) Valid for Spring ( check rates) Summer is $1200 per week, excluding lobster weeks which are $1700. 2018 Winter rates are $5200 per month for Jan Feb Mar, only... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    5 of 5 bubbles Reviewed 1 week ago
    We had the pleasure of staying the month of January at Key Colony beach in the Florida keys. We stayed at 591 9th Street, a cute house on the canal. We could walk, run or bike...
    5 of 5 bubbles Reviewed 28 November 2016
    Because we are getting ready to leave. Dee was wonderful and the house is as advertised and more!! Beautiful house and grounds, more than enough room for a couple and perfect...
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    1 / 14
    5 of 5 bubbles (25) Excellent
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 15 February 2017
    Rented this place for my sister's bachelorette party and we had an amazing stay. It really is walking distance to everything and the shared pool was great. It was such a bonus...
    4 of 5 bubbles Reviewed 15 February 2017
    Key West Bahama House is located in the perfect spot. Rooms are very nice and clean. The only downside in April of 2016, there was construction at the building behind and beside...
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    1 / 12
    4.5 of 5 bubbles (16) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Washer
    • Balcony
    • Internet Access
    • Air Conditioning
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    • Grill
    • Outdoor Dining Area
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 25 October 2016
    Really enjoyed my stayed, I Will definitely will stay hear again, everything was just as expected, location was great, owner was fantastic and very helpful, apartment was very...
    4 of 5 bubbles Reviewed 18 August 2016
    Two bedroom, two bathroom condo suite with patio, across the street from the water. Each bathroom is connected to a bedroom, with the master bedroom having private access, of...
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    1 / 19
    5 of 5 bubbles (3) Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
    • Patio
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Children's Pool
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 bubbles Reviewed 6 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...
    5 of 5 bubbles Reviewed 7 April 2016
    Very nice, quiet, low key place to stay. Great location, in walking distance of many restaurants. Would love to stay again in the near future!
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    1 / 14
    4 of 5 bubbles (2) Very good
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautifully furnished and newly renovated condo is airy and offers all the comforts of your own home. Walk in to a spacious living room with an adjacent dining area and then onto a full kitchen with everything necessary to prepare and serve your meals. The kitchen has granite counter tops, a... View all property information
    Location Information
    Marathon, Florida Keys 33050
    4 of 5 bubbles Reviewed 1 December 2016
    Great location and beautifully decorated. We had all that we needed. We did have some trouble getting in to the unit since we arrived late in the evening, but it was resolved...
    4 of 5 bubbles Reviewed 10 November 2016
    Place was great one of the best I have in in the keys but when we left they tried to say we had left the house in a mess but every room was scrubbed clean and took photos in case...
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    1 / 22
    5 of 5 bubbles (3) Excellent
    Key West
    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
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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.<BR>This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 26 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...
    5 of 5 bubbles Reviewed 23 November 2016
    Lovely clean condo with great views of the salt ponds. Fully equipped with everything you need. Great having a supermarket on site too.
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    1 / 51
    5 of 5 bubbles (4) Excellent
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Satellite TV
    • Washer
    • Air Conditioning
    • Sauna
    • Private Outdoor...
    • Hot Tub
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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. Beautifully decorated by an interior designer. Custom bathrooms and modern kitchen with stainless appliances. Wireless Internet. This is your home... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 16 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 the...
    5 of 5 bubbles Reviewed 14 June 2014
    This vacation rental was huge, nicely decorated, and a great place to stay. The pool, jacuzi, pool house, and courtyard were all amazing - so nice, we spent one full day just...
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    1 / 55
    5 of 5 bubbles (16) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • Waterfront
    • Satellite TV
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Its all about being newly renovated, on the top floor of the best building with the largest end unit with the most windows - twelve. You will have the most magnificent unobstructed ocean views from the living room, kitchen, master & guest bedrooms and balcony. This unit sleeps four adults, (the... View all property information
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 bubbles Reviewed yesterday
    We've stayed at various units in the Ocean Point Complex and this building (400) and unit (4416) are by far the best! End unit on the top floor offers extra windows, all with...
    5 of 5 bubbles Reviewed 2 weeks ago
    We stayed in this beautiful condo for the second time, having visited last May. As before, every detail was perfect and our every need was addressed. The ocean view, overlooking...
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    1 / 15
    5 of 5 bubbles (8) Excellent
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • DVD Player
    • Parking
    • Shared Garden
    • Air Conditioning
    • Balcony
    • Terrace
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    When you arrive, you know you've come somewhere very special. This condo has the most spectacular views of the the Atlantic Ocean and a pristine heated pool. Located on Coco Plum Beach in Marathon, Florida Keys, you're in a secluded yet central base for all Keys sightseeing and activities, if you... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 bubbles Reviewed 24 April 2016
    We traveled with our adult children and 2 grandchildren. Condo #33 has everything you need, and is roomy. Screened in balcony keeps and bugs that may be around outside. View is...
    5 of 5 bubbles Reviewed 18 August 2015
    We had a great time on our first family vacation to the Keys. Marathon is perfectly situated right in the middle. Lots to do right in Marathon. A visit to the Sea Turtle...
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    1 / 9
    5 of 5 bubbles (5) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Parking
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This spacious 2/2 has a giant deck for lounging with pool, shuffleboard and horse shoes on property. Boat slips available and just 10 minutes by boat to the reef. Walk to Sharkeys pub for some awesome food. Dive and Charter boats are just 5 minutes away on foot! This is THE place to stay in Key... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 bubbles Reviewed 18 February 2017
    This is a great location; but, a bit secluded, so it's quiet. Right across the street is a great restaurant, "Sharkey's," that grilled to perfection the snapper we caught onthe...
    5 of 5 bubbles Reviewed 27 October 2016
    Stayed here with my husband and our friends (another couple). We go to Key Largo every year and have been getting hotels so we decided to share a condo this year. Cecil was...
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    1 / 15
    4.5 of 5 bubbles (79) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Air Conditioning
    • Hot Tub
    • Satellite TV
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 1 week ago
    Thanks Steve and Sue. You made our stay in the Keys so memorable. Your condo was so well stocked and wonderful. We came with 2 children under 3 and they had a blast in the pool...
    5 of 5 bubbles Reviewed 4 weeks ago
    This condo has everything you need, from beach chairs to all your kitchen supplies. It was clean and bright. The pool was wonderful, and the location was quiet. You won't be...
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    1 / 13
    4.5 of 5 bubbles (3) Very good
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Grill
    • Wi-Fi
    • Washer
    • Ocean Views
    • Balcony
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautifully refurbished 4th floor condo has great marina and ocean views from the living room, master bedroom & balcony! Gorgeous wood floors throughout and new furnishings lend an elegant atmosphere with lots of comfort in mind. Master bedroom has a king-sized bed, while guest bedroom has 2... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    4 of 5 bubbles Reviewed 25 February 2016
    Four of us rented this location for four days before leaving on a cruise. When we arrived to pick up our keys at the real estate office about an hour before check-in time, the...
    4 of 5 bubbles Reviewed 14 June 2015
    The view was beautiful, the condo was nicely appointed, but the but the amenities were lacking. The salt water lagoon was more of a swamp and there was no beach to speak of so I...
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    1 / 19
    5 of 5 bubbles (4) 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
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles 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...
    5 of 5 bubbles Reviewed 23 July 2016
    This place was in a great location, beautiful view, nicely furnished, perfect in every way. Would definitely stay next time I'm in the area!
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    1 / 18
    5 of 5 bubbles (7) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 bubbles 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...
    5 of 5 bubbles 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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    1 / 26
    Tavernier
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Children's Pool
    • Satellite TV
    • Wi-Fi
    • Secure Parking
    • Air Conditioning
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    Tavernier, Key Largo 33037
    1 / 23
    5 of 5 bubbles (1) Excellent
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Parking
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Perhaps the best value in the Curry House, Room four is simply stunning. The walls have remained unpainted, revealing the solid construction of native, Dade County pine which is naturally resistant to the adverse effects of the local environment. Room Four shares a bathroom with Room 3. The... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 17 May 2016
    Sandy and her team at Curry House are friendly, helpful and welcome you to the B & B with a warm smile and they give you a hug when you leave. I went with my partner and our room...
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    1 / 21
    5 of 5 bubbles (1) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Sauna
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. For two couples or a family with 2 kids. The two new extra long twin beds in 2nd bedroom convert to a comfy King Bed! Master bedroom has new king bed, ocean view and private bath. 2nd bathroom in hallway. This... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 bubbles Reviewed 11 July 2016
    Beautiful ocean views! Nicely decorated and well-cared for condo. We hope to return next year. We had everything we needed and felt like we were at home, a lovely relaxing home.
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    1 / 30
    4 of 5 bubbles (1) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • ?
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    • x
    About this property
    One-half block off world famous Duval Street sits the beautifully renovated home in the 500 block of Olivia Street. The updated kitchen features granite counter tops and beautiful wooden floors. Your bathroom offers a large walk-in tiled shower. A semi-private pool with waterfall feature(shared... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 2 weeks ago
    Clean, quaint, and comfortable. The office help was great, and cleaning service was good. This is close to all of the action while maintaining a peaceful night's sleep.
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    1 / 6
    4.5 of 5 bubbles (6) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
    About this property
    Escape to Key Largo's ultimate weekend or vacation getaway ~ the best Inn in the Florida Keys. Located directly on the Atlantic Ocean, in unspoiled Largo Sound. Offering the best access to the finest of Florida Keys charter fishing, Everglades's excursions, Eco-tours, snorkeling and scuba diving.... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 bubbles Reviewed 10 February 2017
    My husband and I reserved a suite on the ground floor which was both convenient and lovely. The Inn was a quiet oasis minutes from Pennekamp state park and was just what we were...
    5 of 5 bubbles Reviewed 5 June 2015
    one of the nicest place&staff i have ever rented hope to go back soon and visit gilda & crew DANNY&SHIRLEY TRY IT YOU WILL LIKE IT DANNY
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    1 / 33
    4.5 of 5 bubbles (3) Very good
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • Sauna
    • Children's Pool
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to your home away from home! “Bel Cielo” is a beautiful two-story condo in the quaint community of Moon Bay, located at mile marker 104 in Key Largo. (Moon Bay was recently featured on HGTV's Beach Front Bargain Hunt!) Featuring 1,146 square feet of living space with handsome furnishings,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 bubbles Reviewed 20 August 2015
    The condo is beautifully decorated. Furniture is gorgeous and functional. Love the local photos throughout. The location of the condo inside Moon Bay is wonderful. Literally...
    4 of 5 bubbles Reviewed 11 August 2014
    Bel Cielo is nicely furnished and well maintained. An abundance of bath and beach towels is included and the kitchen is fully equipped. The owner responded promptly to questions...
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    1 / 9
    4.5 of 5 bubbles (2) Very good
    Marathon
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Comfortable studio condo with full kitchen and a full size pull-out couch for extra guests. This condo has full resort amenities from a marina with boat dockage, heated pool, tennis & basketball courts, bicycles, canoes, kayaks, paddle boats, tiki huts with picnic tables and charcoal grill, along... View all property information
    Location Information
    Marathon, Florida Keys 33050
    4 of 5 bubbles Reviewed 8 December 2016
    Great location for exploring the Keys. The studio is comfortable and well equipped although it does have wifi we found it to be very weak. Resort is well maintained and the staff...
    5 of 5 bubbles Reviewed 30 July 2016
    We loved it here. Perfect accommodations for three and in the heart of Marathon. Has everything u need to enjoy a wonderful vacation.
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    1 / 14
    5 of 5 bubbles (11) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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.... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 24 January 2017
    We rented the condo and it was the best decision I've made! Mrs. Bonnie was very pleasant and explained all about the property. It was very clean and neat! It had enough utensils...
    4 of 5 bubbles Reviewed 16 April 2016
    The condo was clean and equipped with the necessities and a washer/dryer. Location is away from downtown but we knew that when we booked it. Would definitely rent again and price...
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    1 / 25
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Children's Pool
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on... View all property information
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    Islamorada, Florida Keys 33023
    1 / 33
    5 of 5 bubbles (1) Excellent
    Key West
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of Banana's Foster Guest House This spacious 2 bedroom apartment takes up the first floor of this historic Key West home located on the corner of Caroline St and Simonton Dt. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    4 of 5 bubbles (8) Very good
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Top floor suite! Beautifully furnished condo overlooking the aqua-blue waters of the Gulf of Mexico! This 1,700 sq. ft. , custom decorated condominium offers a unique water vista from the living areas. The split floor plan provides privacy as the bedrooms are on each side of the living/dining area.... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 bubbles Reviewed 28 August 2016
    This was our second stay at this property. We loved the condo first time around and it was even better for this stay with improvements to the condo and all building works...
    5 of 5 bubbles Reviewed 27 October 2014
    Lovely, clean and well furnished condo with great view onto the Gulf. Condo was large with ample room for all six of us with screened verandah ideal for relaxing and watching...
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    1 / 18
    5 of 5 bubbles (1) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 4-6 people. Enjoy the tennis courts, large pool on the ocean, beach-side BBQ grills. Relax, dine and drink under one of the tiki huts or visit one of the many water-front restaurants and bars nearby.... View all property information
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    Islamorada, Florida Keys 33070
    1 / 52
    5 of 5 bubbles (14) Excellent
    Key West
    Studio, 4 Bathrooms, Sleeps 16 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Almost Southernmost Retreat is made up of ALMOST SOUTHERNMOST and ALMOST SOUTHERNMOST TOO on the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker cottages, the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 2 January 2015
    Three generations, nine people, stayed here over Christmas. We each had space to be by ourselves, and we all had space to get together. Nine of us sat around the table in the...
    5 of 5 bubbles Reviewed 3 September 2014
    I came to the Almost Southernmost Retreat for my friends bachelorette party for Labor Day weekend 2014. We had 12 girls and there was more than enough room for everyone. This...
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    1 / 13
    4.5 of 5 bubbles (2) Very good
    Marathon
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Outdoor Dining Area
    • Satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This condo has full resort amenities: Marina with boat dockage, heated pool, tennis & basketball courts, bicycles, canoes, kayaks, paddle boats, tiki huts with picnic tables & charcoal grills, security and wifi. Waterfront to the beautiful Gulf of Mexico, parking for boat trailers, with plenty of... View all property information
    Location Information
    Marathon, Florida Keys 33050
    4 of 5 bubbles Reviewed 31 January 2017
    The unit was beautifully decorated and we were comfortable there. The Gulf view was great, right out our door. The other people were friendly and everyone seemed happy to be...
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    1 / 22
    Key Largo
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    • Satellite TV
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Resort in Key Largo, located in the town of Tavernier, Florida, is at the southern tip of Key Largo island Enjoy a resort in southern Florida's subtropical zone, with easy water access, a hotel bar and restaurant, and fun Florida Keys town nearby. This location is keen for those who like to get out... View all property information
    Location Information
    Key Largo, Florida Keys 33070
    1 / 30
    5 of 5 bubbles (3) Excellent
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    You are downtown with a pool at Flip Flop Retreat- just 2 blocks from Duval Street in a quiet poolside condo in Truman Annex. We have 33 all 5 Star Reviews on a competing website- our guests are very pleased with their vacations. You are in Old Town for convenient entertainment, shopping,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 23 November 2016
    This was our second time renting a this wonderful Condo. Owner is always updating his condo and likes feedback from renters.Plenty of pans, glasses and dishes but only has 4...
    5 of 5 bubbles Reviewed 4 January 2016
    My wife and I along with our son and daughter have been travelling to Key West for several years now and the past few we have stayed at the Flip Flop. As of now I can not think...
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    1 / 22
    5 of 5 bubbles (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautiful motor yacht is available for your exquisite Key West vacation! . Huge Salon, Large galley, gorgeous teak throughout. One queen bedroom and one full bedroom with bathrooms for each one. Forward on the bow are 2 very comfortable loungers with pillows for relaxing. The upper deck is... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 4 weeks ago
    Staying on this yacht was a wonderful experience! We stayed at the dock and could walk to the restaurant (Dante's) and pool. I went fishing and could take my catch to Dante's...
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    1 / 20
    4 of 5 bubbles (4) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Secure Parking
    • Washer
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    • Hot Tub
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    • Satellite TV
    • Balcony
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Come down and take part in in Key West's many fishing tournaments! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family friendly condo in... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 10 February 2014
    I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
    5 of 5 bubbles Reviewed 26 October 2013
    A very nice accommodation. Very well thought out and presented. Faultlessly clean and well maintained. Pauly was quite kind and took great pains to ensure our complete...
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    1 / 34
    4.5 of 5 bubbles (23) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool...
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Abaco Suite, is a bi-level suite with a very spacious... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 2 June 2016
    Secure, gated community. Each unit was part of a duplex/townhouse. Close to Duval Street without all the noise. Home was clean and very spacious. Tons of drawer space, decent...
    5 of 5 bubbles Reviewed 31 May 2015
    As good as the unit was and it really was its the people behind the organisation that make the difference ! I had stuffed up my original booking by 4 weeks, hey I'm old, it's...
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    1 / 15
    5 of 5 bubbles (4) Excellent
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Washer
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    • DVD Player
    • Porch
    • Balcony
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    • Outdoor Dining Area
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 10 March 2016
    First time renting from Trip Advisor. The entire process went very smooth & would definitely recommend it. Stayed at this location for a week with spouse and another couple...
    5 of 5 bubbles Reviewed 19 March 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
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    1 / 29
    5 of 5 bubbles (2) Excellent
    Key West
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Balcony
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    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM to 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 1 week ago
    Our location was the Sunrise Suite located one mile from the Airport. The place was clean and comfortable. Every time we needed a ride to Old Town, Steve always deliver and on...
    5 of 5 bubbles Reviewed 12 May 2016
    We're the type of people who like to be away from the massive partying, and this was the perfect location. Even though you always can't get away from it completely, we feel like...
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    1 / 25
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Venture Out Unit 411 is a waterfront unit with 35' of dock space and Wi-Fi internet access that will provide you with all of the comforts of home. Rather than be cramped into a simplistic motel room, you'll have all of the benefits of having a kitchen, dining room, living room, two bedrooms, two... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 30
    4.5 of 5 bubbles (8) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Papa's Hideaway was a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval street. The perfect mix of location, atmosphere and value. Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 bubbles Reviewed 14 January 2015
    Well, talk about HIGH season. Prices are dear and the lines of cars down the highway get longer each day between Xmas and New Year's. But Key West is a special place, at least Old...
    5 of 5 bubbles Reviewed 23 December 2014
    Stayed for a week before Christmas 2014. I did a bit of research on different properties/hotels, and really wanted to get away from the traditional 'resort' style accommodations...
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    1 / 26
    4 of 5 bubbles (25) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 10 September 2015
    I just returned from a long weekend in beautiful Key West and the Verde Suite was a perfect choice. It was clean, comfortable and just far enough away from the hustle of the town...
    4 of 5 bubbles Reviewed 1 July 2015
    We really enjoyed our few days here and thank goodness for the refreshing pool because it was HOT HOT HOT! We enjoyed meeting a couple of other folks in the quaint cluster of...
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    1 / 9
    4.5 of 5 bubbles (4) Very good
    Islamorada
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Secure Parking
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    This wonderful room opens up into a garden with a water pond. It includes a/c, coffee maker, TV, free WiFi, heat, microwave, refrigerator, shared bath with one other couple. Pool on premises. Close proximity to the beach. Includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    3 of 5 bubbles Reviewed 18 December 2016
    Appealing features: Convenient location. The grounds were beautiful, with a little waterfall, trees, plants and interesting art around little sitting areas in the courtyard...
    5 of 5 bubbles Reviewed 26 May 2016
    I recommend this B&B to anyone who just wants a beautiful property to relax and enjoy the company of your significant other. The staff is very attentive and accommodating and the...
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    1 / 22
    5 of 5 bubbles (2) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Sauna
    • Ocean Views
    • Satellite TV
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
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    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 25 October 2016
    Fantastic. No other word describes it better. The view, the amenities, the layout of the condo...all fantastic. Owner is a very nice lady too. Very easy to deal with. Will...
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    1 / 15
    4 of 5 bubbles (5) Very good
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Sauna
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Balcony
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 bubbles 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 about...
    4 of 5 bubbles 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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    1 / 20
    5 of 5 bubbles (1) Excellent
    Summerland Key
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • Washer
    • DVD Player
    • Private Outdoor...
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Amazing canal front 3 bed 2 bath open concept house located in prestigious community of Summerland Key Cove. It is the first canal from open water and one of just a few flow-through canals providing excellent water quality. The canal is deep and wide. Expect to see lobsters, crabs and other sea... View all property information
    Location Information
    Summerland Key, Lower Keys 33042
    5 of 5 bubbles Reviewed 26 March 2016
    Whatever I'd hoped for, this vacation home has without question, surpassed any and all expectations! Excellent location; in a quiet and beautiful strip. Loved relaxing on the...
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