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Rentals with Pools in Key West, FL

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    1 / 14
    4.5 of 5 bubbles (32) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 17
    4.5 of 5 bubbles (27) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 14
    5 of 5 bubbles (22) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 17
    5 of 5 bubbles (13) Excellent
    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 February 8, 2016
    This is a roomy two bedroom apartment, very clean and nicely decorated. You couldn't ask for a better location to all things around downtown Key West - one block off of Duval...
    5 of 5 bubbles Reviewed February 3, 2016
    This is a beautiful unit in a perfect location. There are 2 bedrooms with very comfortable beds, and two bathrooms. One bathroom is full size and the other is rather small, but...
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    1 / 39
    5 of 5 bubbles (36) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 2 weeks ago
    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 August 5, 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 / 12
    4.5 of 5 bubbles (15) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed October 25, 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 August 17, 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 / 15
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • 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 March 9, 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 March 18, 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 / 14
    4.5 of 5 bubbles (8) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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 February 9, 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 December 29, 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 / 14
    5 of 5 bubbles (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
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    • Terrace
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    • x
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    • 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
    4 of 5 bubbles Reviewed April 15, 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...
    5 of 5 bubbles Reviewed March 5, 2016
    Condo is a $25 cab ride including tip (2016 prices) from Duval Street area where most bars/restaurants/shopping/tourist sites are located. However all cab companies were familiar...
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    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
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    • x
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    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. This is one of a kind unit that is the best in the property with ocean and pool view and largest balcony on the third floor. One- king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 6
    4 of 5 bubbles (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed September 18, 2015
    I would definitely stay here again! It was a great trip with a lot of memories made thanks to the wonderful owner of this apartment. It was the perfect space in the best location...
    4 of 5 bubbles Reviewed May 25, 2015
    This room had all the comforts of home. A bit dated, but very clean. A bit of a drive to Duvall though. About a 10-12 min cab ride. We were there with 6 people and the cab drivers...
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    1 / 17
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The "SeaJay" at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed March 8, 2016
    The condo was great, had all the amenities! Perfect location, right across from the beach, beautiful view! Plus it wasn't far from downtown.
    4 of 5 bubbles Reviewed July 19, 2015
    Myself, my husband, my sister and brother-in-law had visited Key West on a cruise and wanted to return for a week vacation. I rented this condo because of it's location to a...
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    1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Private Yard
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    • x
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    • x
    About this property
    Garden Oasis is a first floor condo in the Shipyard Condos in Truman Annex. We are ideally located 2 blocks from the action (restaurants, shops, clubs) of Duval St., and very short walks to sunsets at Mallory Sq, and the beaches of Ft. Zachary Tayler Park. The Shipyard is a lushly landscaped... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Balcony
    • Ocean Views
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Why stay in one room in a hotel when you can have a whole home? This home has 2 bedrooms, large living room/dining room combination that opens to a deck, and it's own reserved parking space. There is a great community pool that has lots of tropical landscaping and an exercise room in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    4 of 5 bubbles (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Secure Parking
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    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 February 10, 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 October 25, 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 (5) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
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    • x
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    • x
    About this property
    Best Deal in Truman Annex - Céad Míle Fáilte (Irish) 2 Bedroom 1 bathroom Condo - sleeps up to 5 Here's Céad Míle Fáilte to friend and to rover That's a greeting that's Irish as Irish can be It means you are welcome a thousand times over Wherever you come from, whosoever you be. Welcome to our... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed March 17, 2016
    This was my 2nd time staying in the Shipyard section of the Truman Annex. Each time was in a different 2BR condo. this condo was clean, well equipped with kitchen, bath...
    5 of 5 bubbles Reviewed January 24, 2016
    I attended college at a later age and upon graduation took 2 friends and my sister to Truman Annex for a 10 day vacation!!! We had the best time. As a matter of fact I am back in...
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    1 / 21
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class member only marinas. Guests have access to private pool, tiki bar, fine dining restaurant and free laundry. Take it out for a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 2 days ago
    Great boat wth the usual boat accommodations. Very clean and spacious but as always boats are boats so there is always the unexpected. Great experience if you are looking for...
    5 of 5 bubbles Reviewed 1 week ago
    My family and friends stayed on Tim's catamaran yacht for two nights in October. We were six adults, two teenagers, and two toddlers. The vessel had plenty of space to...
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    1 / 22
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed October 24, 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 / 51
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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 July 15, 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 June 13, 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 / 23
    4 of 5 bubbles (45) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    OSPREY COTTAGE: This cozy cottage is located in The Colony Suites, a tropical compound nestled in the heart of Old Town Key West. Osprey offers all the amenities for two who want a larger space than a hotel room but appreciate the amenities of a vacation rental. Sunny and bright this cottage has... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed July 24, 2016
    We stayed at the osprey in bungalow #8. This place was clean with a very comfortable bed, sitting area, kitchenette with a full size refrigerator and a nice deck for morning...
    5 of 5 bubbles Reviewed March 21, 2015
    We walked everywhere and, in fact, never moved our vehicle. The cottage is cozy, clean and comfortable and the pool is great. Having a washer and dryer on the property was...
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    1 / 32
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • ?
    About this property
    Location, Location, Location! Ocean View, Lagoon Beach Front. This 83' Luxury Houseboat is located at 6000 Peninsular Ave. Key West, FL 33040, slip 25. The property is furnished and includes: linens, towels, 3 bedrooms, 3 beds, 2 full baths, 1 Large pull-out couch, all kitchen appliances,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed February 1, 2016
    The boat is big and very comfortable for my family (5) very luxurious to the smallest details, has a jacuzzi on the top and kajacs to navigate the beautiful sea. It was awesome...
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    1 / 12
    4.5 of 5 bubbles (5) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed October 26, 2016
    Very nice condo, I will rent it again next time. With a covered parking spot. Convenient to everywhere. Close to the beach and a nice pool.
    3 of 5 bubbles Reviewed October 14, 2015
    Location, while good very close to Airport which was noisy at times. Bedrooms good size. However, plastic mattress protectors were uncomfortably hot, unnecessary and had to be...
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    1 / 30
    5 of 5 bubbles (3) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • Pet-friendly
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    • x
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    • 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 2 weeks ago
    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 January 4, 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 / 26
    5 of 5 bubbles (36) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • ?
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    • x
    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 1 week ago
    This was our third visit to Casa del Sol, and if it's possible, it was better than ever. New furniture, new mattresses, soft towels and bed linens, a well-stocked kitchen, and the...
    5 of 5 bubbles Reviewed 4 weeks ago
    We stayed at Casa Del Sol while in Key West for my daughter's wedding. Great accomodations, great location.... we had a wonderful stay. Everything you need for your stay is there...
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    1 / 24
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • ?
    About this property
    Coral Casita - Weekly Vacation Rental Completely Re-Designed, Re-Decorated and Ready for your island adventures! When Key West is calling your name and nothing else will do, Coral Casita is the perfect mix of location, price and room for your large group to gather. A spacious 3 bedroom townhome... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    THE DOLPHIN HOUSE: Two houses with the comfort of one. The Dolphin House comprises a main house and a guesthouse with pool and outdoor living space comfortably nestled in between. Enter the main house into the spacious, open and airy great room with vaulted ceilings and a wall of French doors that... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed January 29, 2014
    The location is perfect for those that want a perfect mix of quiet but close to the action on Duval. The décor was beautiful, pool and outdoors perfect. Great area for grilling...
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    1 / 27
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights***<BR><BR>MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS<BR><BR>Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed March 17, 2015
    Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit. The condo has been nicely redone and very well stocked...
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    1 / 9
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Steps from the Ocean, Esprit du Vent is a spacious catamaran within minutes of Key West on Stock Island in a yacht club setting with a pool, beach and restaurant. The catamaran has 3 cabins, 1 head, and is bright, airy and spacious. Fully equipped with galley kitchen, oven, stove, coffee maker,... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    5 of 5 bubbles (71) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    This is a non-smoking condo (smoking on the balcony only) with that "home away from home" appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 1 week ago
    We couldn't wait to come back to Key West and stay here at Pam's condo. This place feels so welcoming and comfortable. The condo has a great view off the balcony. Everything you...
    5 of 5 bubbles Reviewed 3 weeks ago
    Very nice condo! Very clean and comfortable! Would definitely rent it again if going to Key West. Nice location too!
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    1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    • ?
    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (10) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    ISLAND WIND: When balmy breezes beckon and tropical retreats call your name, Island Wind will be just the escape you need. Located in the pristine gated community of Windward Park this 2 bedroom, 2 bath Bahamian-style townhome is surrounded by lush landscaping and views of a sparkling swimming... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed May 26, 2016
    Spent a a week here. We loved everything about it. Great neighbors and relaxed atmosphere. House was absolutely perfect. Everything you need is there, just bring a bathing suit...
    4 of 5 bubbles Reviewed December 5, 2013
    Enjoyed Thanksgiving week here. Island Wind is in a perfect location. It is an easy walk to the southern most beach & a doable walk to Mallory Square. Duval is only a block...
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    1 / 23
    4.5 of 5 bubbles (36) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    CONCH WIND: Conch-style townhome in Old Town Key West nestled in a quiet, secure compound. Open floor plan with spacious living room and dining area with an open kitchen. A separate private deck just off the dining area complete with laundry closet. Guest bedroom on the main level with 2 twin beds... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed January 17, 2016
    This place is very nice and has all the convenience's of home. Located one block off of Duval street so you can walk Duval, drink and not have to drive home. The weather was...
    5 of 5 bubbles Reviewed May 14, 2015
    Very easy to rent. Beautiful. Pool well kept. Clean. 1 1/2 blocks from Duval and Truman trolley. Plenty of space. Would recommend and would stay there again.
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    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
    About this property
    Fully furnished cottage home in the heart of old town key west. This place is perfect for a couple as the house is cozy and comfortable. Loft with Queen Bed overlooking the living room. Cathedral ceiling and Hardwood floors. This place has everything you need to live comfortably while steps from... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    5 of 5 bubbles (52) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
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    About this property
    SHIPYARD TREASURE: 2 bedroom 1 bath Shipyard condo has it all. Located in Truman Annex, there is a shared pool, off street parking and 24 hour security. Shipyard Treasure is a 2nd floor condo with private full-length balconies front and rear. This property has an open and airy feeling and is one... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed February 18, 2015
    Shipyard Treasure is welcoming, comfortable, condo, decorated with Key West art in the bedrooms, living room, and entry, and with wonderful beds, bedding, and much better than...
    5 of 5 bubbles Reviewed March 16, 2013
    My family had a wonderful vacation while staying at the Shipyard Treasure. The condo was tastefully decorated and was stocked with all the comforts of home. The location was...
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    1 / 24
    4.5 of 5 bubbles (25) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    KEY WEST CASA: One of only a few 3 bedroom 2 bath condos in the Shipyard complex in Truman Annex. Enter the fully stocked kitchen to the living room to the French doors that open onto the back porch. The downstairs bedroom is just to your left and offers 2 twin beds next to the bathroom. Upstairs... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed June 12, 2016
    We stayed in Key West Casa and absolutely loved that property. It is a 3 bedroom, 2 bath with a porch, back patio, balcony. The kitchen is fully equipped, one of the best we've...
    4 of 5 bubbles Reviewed April 9, 2014
    Check-in & out was excellent, no problem, Great! It was so nice to feel like you were home and not stuffed in a little one room. The location is perfect, you are close to...
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    1 / 23
    4.5 of 5 bubbles (27) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    BEACH HOUSE CONDO: 2 bedroom 2 bath downstairs condo in the gated Shipyard Condominium area of Truman Annex. The perfect back deck to sip a cafe con leche or read a book. Open floor plan with kitchen, dining area for 4 and living room that opens to a large private deck. The master bedroom has a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed April 13, 2015
    Lovely condo in a gated community! 5 min walk to pool, 8 minute walk to beach. Accommodations lovely and patio very nice. Centrally located, 2 blocks from Duval. A lovely spot...
    5 of 5 bubbles Reviewed May 8, 2014
    My wife and I have been vacationing in key west for the past fourteen (14)years. This is the first time we did not stay in the hotels. The condo we rented was very Comforable and...
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    1 / 24
    4.5 of 5 bubbles (32) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    FINN KEY: 2 bedroom 1 bath downstairs condo in The Shipyard section of Truman Annex, one of the most popular spots in Old Town Key West. Remodeled with attention to detail, the kitchen sparkles with top of the line appliances, cabinetry and every amenity needed. Opens to a sunny living room... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed February 10, 2016
    Lovely condo,great location, have stayed at Truman many times. Condo is clean and comfortable, neighbors upstairs must live here full time, they walk a little heavy but I suppose...
    4 of 5 bubbles Reviewed May 12, 2015
    Registration on line was easy, good communication from rental agency. Agency is off site so key pickup and drop off is not as convenient as with Compass Realty, a different rental...
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    1 / 16
    4.5 of 5 bubbles (49) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed October 19, 2016
    Returning to Ann Street. Such a comfortable bed!! We love the little Ann Street compound with its secluded pool and lush gardens. Tranquility was the perfect size for us two...
    4 of 5 bubbles Reviewed September 19, 2013
    Owners were unbelievably nice from the beginning of communication with them! This cottage lives up to its name. I'm pretty sure the maid skips the bathroom when she cleans in...
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    1 / 23
    4.5 of 5 bubbles (22) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    LINGER LONGER: 2 bedroom 1.5 bath townhome in Truman Annex. Master bedroom with queen bed and guest bedroom with trundle that converts to 2 twins are on either side of the full bathroom on the 2nd floor. Downstairs is an open floor plan with kitchen/dining/living room and half bath. French doors... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed May 18, 2015
    I am a repeat renter and plan to return next year. Walking distance to everything but in a quiet community off Duval.
    4 of 5 bubbles Reviewed April 27, 2014
    This was the first trip to Key West for my husband and I, but we traveled with more experienced Key West-ers who booked the rental. We were pleasantly surprised when we arrived at...
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    1 / 22
    4.5 of 5 bubbles (48) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • ?
    About this property
    DUVAL SEA TURTLE: This townhome has 2 bedrooms and 2.5 baths with a balcony off the master bedroom and the living room. Covered, gated parking space, WIFI, 3 TVs, free long distance calls King mattress, washer/dryer, and living room furniture new in March 2014. There is a community pool area to... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed September 28, 2016
    Just returned from a stay and this property exceeded our expectations. It was a great location in easy walking distance to everything on Duval. The unit was spotlessly clean and...
    5 of 5 bubbles Reviewed July 4, 2014
    Great Location to enjoy all Key West has to offer. CVS for stocking up on snacks, alcohol, basic groceries is right next door. It was great to have 2 baths upstairs and 1/2 down...
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    1 / 16
    4.5 of 5 bubbles (38) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Child-friendly
    • x
    • ?
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    • x
    About this property
    An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this charming 1 & 1/2 story... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed October 17, 2012
    This amazing little house had everything you could need to make a Key West vacation even better. The whole house was clean, and with a tropical flair that told you the moment you...
    5 of 5 bubbles Reviewed September 1, 2012
    The house was spotless. Easy to live in. Close to everything. Comfortable. The small pool/grotto is where I hang out in my memories. Everyone was sweet, accommodating and...
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    1 / 23
    4.5 of 5 bubbles (27) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • ?
    About this property
    CORAL GARDEN: 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock. Fully-equipped kitchen, comfortable dining area, and living room sports a gigantic 52' HDTV for your viewing pleasure. Master bedroom with bath ensuite offers a comfy queen bed; 2nd bedroom with bath ensuite... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed September 12, 2013
    Our visit to Key West was amazing. At Home in Key West Inc. has the best services they were very informal and personal. At Home made sure we had everything that was needed for our...
    5 of 5 bubbles Reviewed August 16, 2013
    We were thrilled to see that the home was so well kept and looked exactly like the photographs. I would definitely recommend people staying here especially if you have children...
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    1 / 29
    5 of 5 bubbles (18) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Grill
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    • Outdoor Dining Area
    • Satellite TV
    • Porch
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Historic Old Town Location - Private Pool - Steps from World Famous Duval Street and the Ernest Hemingway Home! Debating between the comfort of a chic hotel and the thrill of more authentic accommodations? You will get the best of both worlds with this cozy 2 bedroom home, currently available for... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed September 17, 2016
    We stayed at the Potter's Cottage and thoroughly enjoyed our experience. The property was in fantastic condition - fully modern with generally high quality finishes. One full...
    5 of 5 bubbles Reviewed July 27, 2016
    We recently stayed at The Potter's Cottage for a week in July. The cottage itself is lovely and quaint. It has been fully remodeled and was very clean. The rental included bed...
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    1 / 24
    4.5 of 5 bubbles (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • ?
    About this property
    KEY WEST CROWN JEWEL: 2-bedroom, 2-bath, penthouse condominium with 1350 square feet of living space. WIFI, flat-screen plasma television with Bose surround sound system in the living room, as well as TV/VCR/DVD/CD players in each bedroom. Large, fully-equipped modern kitchen with granite... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed March 26, 2014
    We had the great honor of staying in this unit for a week in March. Our teenage daughter had her own bedroom and bath, which was wonderful. The entire condo is clean, well...
    5 of 5 bubbles Reviewed March 14, 2012
    Again thanks to Gale she does a great job and is easy to work with. Have already booked The Crown Jewel for next year and plan to do so for years to come. Thanks Mitch and...
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    1 / 20
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • ?
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    • x
    About this property
    Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 6
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Ocean Views
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    • Pet-friendly
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    • x
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    • ?
    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a "closet... View all property information
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    Key West, Florida Keys 33040
    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This is an amazing summer rental. Available during June and part of July only for either long weekends or by the week. Stunning location within the old town of Key West, over two levels, full kitchen, bbq, 2 bedrooms, shared pool. (Only between 4 houses) It just doesn't get better than this This... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • ?
    About this property
    CITY CAY: City Cay is our 1-bedroom 1-bath upstairs condo in Truman Annex that has been lovingly renovated and furnished in a sleek modern style. Stay connected in the living room with high-end electronics including HDTV, WIFI and an over-the-top stereo system. Relax on the covered back balcony... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed August 1, 2016
    We loved City Cay. It was a small condo with one king bed, a futon and a small kitchen, but it was exactly what we needed. The bed was super comfortable. The bathroom was well...
    5 of 5 bubbles Reviewed January 4, 2015
    We stayed at City Cay over the Thanksgiving holiday. The condo is on the second floor of a building in the Shipyard Annex of Truman's Annex complex. We had wanted to stay in...
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    1 / 24
    5 of 5 bubbles (4) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • ?
    • Smoking allowed
    • ?
    About this property
    CASA GRANDE: Located on a quaint lane steps from Duval Street with room to park 2 vehicles off-street. Built for entertaining from the wide open floor plan that encompasses the spacious living room and grand kitchen to the magnificent pool. Master bedroom with bath ensuite shares first floor with... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed May 6, 2015
    This was our second year at Casa Grande and I recommend highly if you're a group of 8-12 people. Beautiful location near 1100 block of Duval. Nice large pool in backyard, spacious...
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    1 / 23
    4.5 of 5 bubbles (27) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Terrace
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    • Satellite TV
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked for a Key West vacation rental Florida. Fabulous artwork, fun collectibles, beautiful stained glass all give this cottage the unique feel that keeps... View all property information
    Location Information
    Key West, Florida Keys 33045
    5 of 5 bubbles Reviewed June 28, 2015
    The Tranquility Cottage (#5 at The Colony Cottages) is adorable. The cottage is bright, cutely decorated, and the compound is quite inviting. It is conveniently located and an...
    5 of 5 bubbles Reviewed April 6, 2015
    Great unit, very well maintained. Repeat customer and would recommend this to anyone! I would only add chairs to the front porch.
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