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Holiday Rentals with Pools in Florida Keys, FL

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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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    1 / 17
    4.5 of 5 bubbles (31) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 17
    5 of 5 bubbles (14) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 55
    5 of 5 bubbles (14) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Grill
    • 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
    Sunset off the small porch and sun set out the kitchen window was wonderful. The pool and the grounds were well maintained. We never had to wait for a tennis court! Bring...
    5 of 5 bubbles Reviewed 1 week ago
    Stayed here in the middle of January and you couldnt ask for a better spot. Tony makes everything easy and seemless for. The condo has everything you could need for your stay...
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    1 / 14
    4.5 of 5 bubbles (35) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Outdoor Dining Area
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    About this property
    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 2 weeks ago
    Just one block from all the action yet very quiet at night. The Grand Bahama Suite was extremely comfortable for our party of four. Clean, nice amenities, lovely pool and plenty...
    5 of 5 bubbles Reviewed 2 January 2017
    The Bahama House was such a great find. The location was perfect and the pool area was amazing. The house was clean and had all the amenities we could have asked for. Thee...
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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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    • 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 1 week ago
    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 1 week ago
    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 / 14
    5 of 5 bubbles (11) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
    • Balcony
    • Washer
    • Air Conditioning
    • Terrace
    • Hot Tub
    • Parking
    • Wi-Fi
    Suitability
    • 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 4 weeks ago
    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 15 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 / 21
    5 of 5 bubbles (4) 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 1 week ago
    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 / 23
    5 of 5 bubbles (4) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Washer
    • Satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Tavernier, Key Largo 33070 3100
    5 of 5 bubbles Reviewed 9 July 2016
    I started looking for a place to stay for 10 days, the hotels were way to expensive. I happen to stumble upon Ocean Pointe in Tavernier Fl. I rented a timeshare,I didn't book...
    5 of 5 bubbles Reviewed 6 July 2016
    Nice place. Loved the kayaks. Friendly staff. Gated. Rooms are clean. Restaurant on site. Would stay there again.
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    1 / 96
    5 of 5 bubbles (10) Excellent
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Satellite TV
    • Patio
    • Waterfront
    • Grill
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    • 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 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...
    5 of 5 bubbles Reviewed 10 August 2016
    This was a wonderful vacation rental and a great base for touring the keys. Booking with Dee was easy and the cold beverages on our arrival were a welcome surprise! Our family...
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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 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...
    5 of 5 bubbles Reviewed 6 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 / 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
    • Washer
    • Hot Tub
    • Waterfront
    • Air Conditioning
    Suitability
    • 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 / 23
    4 of 5 bubbles (2) Very good
    Key Largo
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Hot Tub
    • Washer
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Grill
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Resort in Key Largo 'located in the town of Tavernier' at the southern edge of Key Largo island, along the designated scenic drive on US Hwy 1. This is a perfect location for those who love to get out onto the water, or to observe the local wildlife. The tropical birds in this area are amazing.... View all property information
    Location Information
    Key Largo, Florida Keys 33070
    4 of 5 bubbles Reviewed 12 October 2016
    My teen son and I stayed at this condo for Fall Break while taking a PADI course at the Rainbow Reef dive center, about a 15 minute drive north. We switched from a closer hotel...
    4 of 5 bubbles Reviewed 8 September 2016
    The unit is not bad at all but definitely NOT what the pictures show. Everything seems to be clean and having a washer and dryer in the unit was awesome. I wish we could have...
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    1 / 19
    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 10 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 / 14
    4.5 of 5 bubbles (8) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 9 February 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 bubbles Reviewed 29 December 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
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    1 / 7
    5 of 5 bubbles (5) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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... View all property information
    Location Information
    Tavernier, Key Largo 33037
    5 of 5 bubbles Reviewed 18 January 2017
    We stayed for a week from the 26th of December to the 2nd of January 2017. We were greeted by Joe who was amazing for recommending local restaurants and a host of activities to do...
    5 of 5 bubbles Reviewed 7 December 2016
    Our stay at the Penthouse Condo in Key Largo Was better than I can describe. The location was perfect, The furnishings were great and above expectations. The owners were...
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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
    • Wi-Fi
    • DVD Player
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    • Shared Outdoor Pool...
    Suitability
    • 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 / 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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    • Smoking allowed
    • 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 1 week ago
    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 / 17
    4 of 5 bubbles (8) Very good
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
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    • Balcony
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    • Waterfront
    Suitability
    • 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 26 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 / 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 6 days ago
    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 26 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
    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
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    • Outdoor Dining Area
    • Satellite TV
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    • 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 9 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 18 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 / 30
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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    • Pet-friendly
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    • ?
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    • x
    About this property
    Part of POOLSIDE PARADISE 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... View all property information
    Location Information
    Key West, Florida Keys 33040
    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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    • DVD Player
    • Hot Tub
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    May Special $299 a night. 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... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 21 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 5 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 / 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 / 30
    4.5 of 5 bubbles (8) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Papa's Hideaway is 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 13 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 / 18
    5 of 5 bubbles (7) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 / 25
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    With its rich wood flooring and triple windows, this selection is truly fit for a king. Wood and cane furnishings and metal sculpted palm lamps with intricate shell shades make the guest feel welcome and relaxed. Double nightstands and a writer's desk add to the atmosphere without compromising... View all property information
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    Key West, Florida Keys 33040
    1 / 41
    5 of 5 bubbles (2) Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium... View all property information
    Location Information
    Islamorada, Florida Keys FL 33036
    5 of 5 bubbles Reviewed 2 February 2016
    We loved our stay at Ocean Harbour Apartments. After viewing photos on your website, we chose this based on the beautiful grounds and lovely accomodations. We could not have...
    5 of 5 bubbles Reviewed 5 January 2015
    This spacious condo is beautifully furnished and equipped. The gated community is very quiet and has a heated salt water pool. There is a nice spot to see the moon and sunrise...
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    1 / 25
    5 of 5 bubbles (1) Excellent
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Patio
    • Waterfront
    • Grill
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    "."
    5 of 5 bubbles Reviewed 9 November 2016
    Everything we expected and more!! Condo very well maintained. Very adequately supplied with everything you need during your stay. Wonderful!! Thank you Susie and Matt for making...
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    1 / 22
    5 of 5 bubbles (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
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    • Hot Tub
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    • Satellite TV
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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 24 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 / 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
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    • Waterfront
    • Satellite TV
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    • 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 22 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 / 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
    • Internet Access
    • 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 25 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 / 33
    5 of 5 bubbles (1) Excellent
    Key West
    2 Bedrooms, 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
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    5 of 5 bubbles (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Hot Tub
    • Satellite TV
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    • Balcony
    • Air Conditioning
    • 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 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 / 23
    5 of 5 bubbles (1) Excellent
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • 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 16 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 / 36
    5 of 5 bubbles (13) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This house is in a quiet residential neighborhood where loud boisterous parties are not appropriate. This 2 bedroom, 2 bath, 2 story house has an open floor plan featuring lots of pine walls and floors throughout. Upstairs is the king bedroom and a full bath and downstairs is the second bedroom... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 9 November 2014
    We were very happy with this house rental. The pictures only hold a small window into this gem. Walking distance to Duval (although a cab was only $6 if needed). Great living...
    3 of 5 bubbles Reviewed 12 August 2014
    Pros - charming cottage, two bathrooms, private pool, dish washer, washer and dryer, nice bed and linens, just a few blocks from Duval, plenty of street parking. Cons - across...
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    1 / 35
    5 of 5 bubbles (3) Excellent
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Wi-Fi
    • Private Outdoor...
    • Waterfront
    • Patio
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Welcome to "SANDY BEACH" in Key Largo, Fl. Enjoy amazing sunsets from your own private white sandy beach and swaying palm trees that leads you into the warm ocean blue waters of the Florida Bay. This gated 1 acre 3/3 pool home has been updated and beautifully decorated. It can sleep 8 to 10... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 bubbles Reviewed 10 June 2014
    This place is truly amazing! The beach is clean and the good sand extends out into the water. The amenities are endless in the house. Kids loved the pool as it gave them a...
    5 of 5 bubbles Reviewed 15 March 2014
    My family of 7 including 2 babies just had a wonderful week at Sandy Beach. The house is perfect for a group with large quiet bedrooms. The outdoor kitchen and beautiful private...
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    1 / 24
    3 of 5 bubbles (1) Average
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Ocean Views
    • Internet Access
    • DVD Player
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    • Private Outdoor...
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    It’s just what you need. Minutes from Miami, yet seemingly a world away. The vacation you deserve is waiting for you in this elegantly well-appointed ocean-side condominium. What's more we understand what you are looking for in a vacation rental. Enjoy the fresh feeling you experience when you... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    3 of 5 bubbles Reviewed 8 November 2016
    This apartment had a great location in Key Largo overlooking a marina area. The owners are really helpful and helped with any questions. It provides good access to the local...
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    1 / 29
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Balcony
    • Hot Tub
    • Terrace
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    • Shared Outdoor Pool...
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    • 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 - 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
    1 / 21
    Key Largo
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
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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 / 22
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Shared Outdoor Pool...
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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
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    Key West, Florida Keys 33040
    1 / 45
    Key Largo
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Air Conditioning
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    • Children's Pool
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Stay at a Luxury Townhome. Recently remodeled... Everything is new! Beautiful kitchen fully equipped , TV in each room, three patios, located just off the heated pool (literally 20 steps away from the pool) plus a kiddy, parking is right outside the front door. Beautiful sunsets from the balcony... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 26
    4 of 5 bubbles (25) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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 9 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 30 June 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 / 13
    4.5 of 5 bubbles (2) Very good
    Marathon
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
    • Grill
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    • Outdoor Dining Area
    • Satellite TV
    • Waterfront
    • Air Conditioning
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    • 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 3 weeks ago
    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 / 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
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    • 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 / 15
    4 of 5 bubbles (9) Very good
    Duck Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Waterfront
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    LATE FALL SPECIAL DEALS; RATES AS LOW AS $125 PER NIGHT. LATE FALL IS GREAT IN THE KEYS!, Situated in the grounds of Hawkscay hotel and resort, on the beautiful upscale island of duck key, this lovely villa boasts a quality recently refurbished interior. Outside there is a waterfront private... View all property information
    Location Information
    Duck Key, Florida Keys 33050
    3 of 5 bubbles Reviewed 29 April 2016
    The property manager who lives locally, was just a very service minded individual who was a pleasure to work with when things didn't go quite as planned. ('advertisers' don't live...
    3 of 5 bubbles Reviewed 2 March 2016
    The villa is a duplex style rental located in Hawk's Cay Resort but is not associated with the resort. The owners sent us in advance via email clear and specific directions on how...
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    1 / 10
    5 of 5 bubbles (5) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    <BR><BR>Luxurious direct bayfront townhome with dock, upgraded unit.<BR><BR> best location in the 50's overlooking large green yard and open bay with slip in front.<BR><BR>3 bedroom, 2.5 bath. Built in 2006. gated waterfront community. Dock for 32 ft boat, beautiful pool, mins to ocean through vaca... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 bubbles Reviewed 13 August 2016
    Repeat customer. This is premiere property for location, views, amenities and well rounded stays. Property is well maintained and serviced, facilities for boating, fishing, ice...
    5 of 5 bubbles Reviewed 12 August 2015
    it was just a great place , we just loved it there , the location to all , the pool and marina was just great , and the sunsets with a drink were just wonderful.
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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
    • Internet Access
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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 / 26
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Shared Outdoor Pool...
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    • Internet Access
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    • 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 - 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