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Pet Friendly Rentals in Key West, FL

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    $170
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    2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 / 23
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 of 5 stars (1) Poor
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... View all property information
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    Key West, Florida Keys 33040
    2 of 5 stars Reviewed May 18, 2015
    Would be lovely with lots of maintenance and repairs. Water leak in the cabin, smells humidity, surage, fridges are sticky from dirt and the fridge door won’t even close. Towels...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Located on a quiet residential street in the beautiful Key West neighborhood of Casa Marina, A Low Key Paradise has a beautiful open layout, with views of the large private patio and pool visible as soon as you enter. Guests can walk to nearby Higgs beach, and Higgs beach dog park— perfect for your... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 1 Bathroom, Sleeps 6
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    • Shared Tennis Court
    • Stereo System
    • Water Park Nearby
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    • Pet-friendly
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    • x
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    About this property
    Elegantly furnished Key West vacation condo in the historic Truman Annex in the heart of Old Town in Key West. This is the premier gated community in Key West, bordering the Atlantic Ocean. Grounds of the Annex are beautifully landscaped. The Shipyard units are done in the traditional Key West... View all property information
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    Key West, Florida Keys 33040
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    1 / 11
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Hot Tub
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    • Gym
    • Private Tennis Court
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    • Internet Access
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    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
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 26, 2015
    Very lovely condo!!! Close to everything you need! It was our first time to key west and when we return we will definitely try to stay here again!!!! We really enjoyed our time.
    5 of 5 stars Reviewed March 22, 2014
    A great condo. All the amenities. Covered parking, close to the pool. Easy access to downtown, either by car or taxi. Wonderful communication with the owner. First time for 4 of...
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    1 / 14
    5 of 5 stars (47) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Air Conditioning
    • Hot Tub
    • Shared Tennis Court
    • Stereo System
    • Private Outdoor...
    • DVD Player
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 3, 2015
    Our stay at the condo was very enjoyable. It had all the comforts of home. We found the location to be great; close enough to downtown, far enough away for quite time! We would...
    5 of 5 stars Reviewed July 14, 2015
    From the beginning to the end, the process of renting the condo was made very easy owners were a pleasure to deal with and the condo was nice, clean and comfortable and all...
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    $215
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    2 Bedrooms, 1 Bathroom, Sleeps 6
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    • TV
    • Washer
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    • Refrigerator
    • Air Conditioning
    • Wi-Fi
    • Dryer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    When you walk into this suite, you are suddenly hit with a taste of luxurious decadence. The bar in the corner will make you wonder when you're partying will start, but the sumptuous couch and other fancy touches will make you think twice about bringing the whole neighborhood in for drinks. The... View all property information
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    Key West, Florida Keys 33040
    From
    $320
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    2 Bedrooms, 1 Bathroom, Sleeps 6
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    • Refrigerator
    • TV
    • Dryer
    • Air Conditioning
    • Wi-Fi
    • Housekeeping...
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    When you walk in to this spacious two bedroom suite, you feel like you walked into a small house. The living room is very expansive and could accommodate an elephant, if you have a yen for those types of parties. Hangover anyone? The larger bedroom has a queen bed, and a surprising cedar lined... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    2 Bedrooms, 5 Bathrooms, Sleeps 6
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    • Air Conditioning
    • Satellite TV
    • Water Views
    • Wi-Fi
    • Hot Tub
    • Watersports Nearby
    • Ocean Views
    • Staffed Property
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • Smoking allowed
    • Elder access
    • x
    About this property
    This property is located on the north side of Key West 4 miles from downtown.It is available from Dec. 27th to January 3rd. A great venue for the holiday season. This is a great two bedroom two bath unit with master bedroom and en suite. Private balcony which overlooks outdoor infinity pool. Also a... View all property information
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    Key West, Florida Keys 33040
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    1 / 30
    4.5 of 5 stars (30) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4
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    • Patio
    • Deck
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    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Andros Suite is a bi-level suite with a very spacious bedroom upstairs with a... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 28, 2015
    We had a large group in 5 of the units for my daughter's wedding and absolutely loved our stay. The townhouses were equipped with everything we could possibly need and very clean...
    5 of 5 stars Reviewed January 12, 2015
    The location was ideal and close to Duval Street. The place was very cozy and perfect for a couple, but definitely roomy for 4 people. We stayed for three nights for New Years...
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    $188
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    1 / 25
    4 of 5 stars (24) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4
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    • Internet Access
    • Linens Provided
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool...
    • Refrigerator
    • Satellite TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed June 30, 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...
    4 of 5 stars Reviewed December 16, 2014
    We were a group of four and rented the Verde Suite for six nights. We arrived to town earlier than check in time and were told the house wasn't ready but we could park at the...
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    1 / 24
    4.5 of 5 stars (39) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5
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    • Washer
    • Internet Access
    • Sauna
    • Water Views
    • Waterfront
    • TV
    • Gym
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Fully Appointed Suite- Condominium Unit- 2 Bedrooms, 2.5 Baths (Sleeps 4-5) Our beautifully landscaped property and contemporary housing will provide you with a serene tropical setting ideal for a relaxing vacation getaway. Located off the azure waters of the Atlantic Ocean, minutes away from... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 20, 2015
    I am an owner at Naples, and have been coming down for the past 5 years, for up to a week, each summer. I started years back trailering my 24 foot bay boat, and now I just drive...
    4 of 5 stars Reviewed August 20, 2015
    Beautiful property. Clean, spacious suites. Perfect for families. Convenient dock and marina. Restaurant service was fine but food was just "ok". Enjoyed being close to Key...
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    1 / 32
    4.5 of 5 stars (12) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Patio
    • Air Conditioning
    • Balcony
    • Linens Provided
    • Satellite TV
    • Waterfront
    • Water Views
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Come stay aboard our FABULOUS houseboat Libra! Docked in one of Key West's most exclusive yacht club marinas, our guests have free access to a host of 'members only' amenities including a swimming pool, private beach, tiki bar, fitness facility, sauna, clubhouse, onsite restaurant, free parking and... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 15, 2014
    We just spent 2 days in the Libra in Key West and what a fantastic stay. Ray is awesome, very helpful and allways available, he cooks also in the New York Pasta Garden and it will...
    3 of 5 stars Reviewed April 24, 2014
    we were on this boat for 3 nights. Before we were 2 nights on the Coconut boat. We liked the Coconut more because it is more cozy, but that is of course our personal thoughts...
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    1 / 28
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Stereo System
    • Internet Access
    • Washer
    • DVD Player
    • Hot Tub
    • Gym
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    My Sunshine Luxury Suite is an upscale property located in Key West, an island paradise. Sunshine Suite provides the luxury and convenience of your own condo home just 90 miles from Havana. Surrounding the resort, you will enjoy lush tropical foliage and amenities such as our tennis court, gym... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 28, 2014
    fabulous condo on a very secure property close to the beaches. Roosevelt Blvd is within walking distance and has a sidewalk large enough for walking and biking along the ocean...
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    1 / 12
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6
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    • Housekeeping...
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Deck
    • Satellite TV
    • Stereo System
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Relax in paradise amongst all the comforts of home in the Sailor House, a proud member of Andrews Inn & Garden Cottages. Just a half a block off the world famous Duval Street, the Sailor House offers the ultimate in privacy and luxurious island living. Families and couples traveling together rave... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 7, 2015
    We went over the 4th of July weekend with a group of friends. Location is still amazing. The major concern was the it never felt as if the AC was cold enough. I am wondering if...
    4 of 5 stars Reviewed April 24, 2015
    Cute two story Key West cottage. Located blocks away from Duval, but yet quiet. Good times were had at the Jacuzzi and the top patio. The swing on the top balcony was nice and...
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    1 / 19
    5 of 5 stars (4) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4
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    • Satellite TV
    • DVD Player
    • Stereo System
    • Air Conditioning
    • Refrigerator
    • Wi-Fi
    • Balcony
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Bella Vita is a 1 Bedroom, 1 bath, luxurious, steps from Duval Street. Bella Vita is the sister unit to the La Dolce Vita in the same building, listing 431504. Please check out our for availability, photos and video. Everything is brand new from floor ceilings! 14... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 2, 2015
    We stayed in this awesome apartment for 5 nights. From the start was updated and informed about everything we needed to know. This apartment is decorated nice and very clean...
    4 of 5 stars Reviewed February 9, 2014
    We stayed in this lovely apartment for 4 nights. The owner payed a lot of works to decorate this apartment, and kept good connection with their guests. I received a lot of...
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    1 / 18
    1 Bedroom, 1 Bathroom, Sleeps 4
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Hot Tub
    • Stereo System
    • TV
    • Housekeeping...
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Eyebrow House is a very spacious one-bedroom suite with a large front porch and palm tree-filled private fenced-in yard overlooking a quiet side street. Our guests enjoy the best of both worlds as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a half block away.... View all property information
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    Key West, Florida Keys 33040
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    1 / 27
    4.5 of 5 stars (12) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Waterfront
    • Patio
    • Air Conditioning
    • Water Views
    • Balcony
    • Satellite TV
    • Linens Provided
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The M/V Coconuts is a completely unique home with 360 degree water views, it also happens to be a 50-foot trawler, permanently docked at the Key West Harbor Marina. This is more than a boat. It really is a very comfortable home, with proper living area, bedrooms and large sundecks. There is over... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 4, 2015
    The ship sleeps six people (one queen size bed aft, two twins that can be pushed together forward, two bunk beds and a pull out sofa). There is a nice kitchen and two gathering...
    4 of 5 stars Reviewed March 1, 2015
    Our family enjoyed the MV Coconuts vacation immensely. The boat is roomy, and provides a unique vacation experience. You can look down into the water anytime of day and see many...
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    1 / 21
    5 of 5 stars (4) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 7
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Private Outdoor...
    • Stereo System
    • Deck
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Chick-A-Pea’s Cottage: Located in the gallery district of Key West. The house is steps off of Duval St. near Hemmingway’s house, the Southernmost Point, the Butterfly Museum and great shops, restaurants and bars . The location is quiet & private… yet in the heart of key west The house is a... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 12, 2014
    My family and fiance stayed at Chick a pea this past may. Todd was wonderful during all of the communication phases, booking and getting into the property. Upon arrival Todd...
    5 of 5 stars Reviewed May 20, 2014
    My husband and another couple went for a week of relaxation. This was the perfect home with all the amenities. The pool and outdoor sitting area is where we spent most of our...
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    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50', 42', and 27' flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 9, 2015
    We loved our stay at Catherine St. The home is set up with everything that you could ever need. The pool is very private. Skinny Dipping a definite. All of the furniture is custom...
    5 of 5 stars Reviewed February 26, 2015
    My husband and I spent both January and February here and loved it. Great beds, lots of room as we had at least another couple stay with us and twice we have three couples. Pool...
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    1 / 12
    5 of 5 stars (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7
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    • Dryer
    • Air Conditioning
    • Refrigerator
    • Balcony
    • Grill
    • Wi-Fi
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 10, 2015
    Absolutely loved our stay. Owners were great to work with. Furnishings were warm and inviting. Would definitely stay again!
    5 of 5 stars Reviewed October 31, 2014
    First of all, this hotel is awesome! We went as a group of 8 women and I was thrilled that we only needed two rooms and they were side by side! Had a balcony, and plenty of room...
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    1 / 12
    1 Bedroom, 1 Bathroom, Sleeps 4
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    • Washer
    • Grill
    • Balcony
    • Refrigerator
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! The property is completely private and safe, surrounded by a 6 foot gated fence and tropical landscaping. Due to local zoning laws we... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    1 / 36
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • x
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    About this property
    Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing,... View all property information
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    Key West, Florida Keys 33040
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    1 / 20
    5 of 5 stars (4) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Internet Access
    • Deck
    • DVD Player
    • Satellite TV
    • There Are Tennis...
    • Washer
    • Watersports Nearby
    • Air Conditioning
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    About this property
    Key West has all of the charms of being away from the world, yet with all of the worldly conveniences near at hand. Located in the historic old town, Namaste Key West is in a quiet residential neighborhood, with beaches 5 minutes away, 3 yoga studios within a block, coffee shops, and a grocery... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 2, 2014
    My husband and I stayed in lovely Namaste from May 15th through Aug 15th and were enchanted the entire time. The house is lovely, even better than the fabulous pictures. It is...
    5 of 5 stars Reviewed April 30, 2013
    The Namaste Cottage was an amazing place to stay during our time in Key West. We spent two weeks at Namaste and were constantly reminded of how central it is to all of the great...
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    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8
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    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Grill
    • Balcony
    • Shared Outdoor Pool...
    • Dishwasher
    • Linens Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • x
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 13, 2013
    Everything was as promised , great location , very nice and helpful staff .
    5 of 5 stars Reviewed January 5, 2013
    Very spacious with great balcony with dock/pool access. Would definitely stay again
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    1 Bedroom, 1 Bathroom, Sleeps 4
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    • Satellite TV
    • Refrigerator
    • Dryer
    • Wi-Fi
    • Housekeeping...
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    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
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    • Elder access
    • x
    About this property
    A True Conch Cottage, for a True Key West Experience When you first see this petite looking cottage, you initially feel like you need to say, 'Awwww, how cute IS this small house?' But then once you walk in you feel quite stunned by how large it actually feels inside. Gifted with an open-concept... View all property information
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    Key West, Florida Keys 33040
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    1 / 33
    5 of 5 stars (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8
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    • DVD Player
    • Grill
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    • Air Conditioning
    • Patio
    • Private Outdoor...
    • Deck
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • x
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    About this property
    Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene hideaway is just moments away from Duval Street and the most exciting spots the southernmost... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 28, 2015
    Fabulous! 1/2 block from Duval and close to all that old town Key West has to offer. The house is very clean, has great outdoor space and the layout is perfect. Best place out...
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    4 of 5 stars (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4
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    • Internet Access
    • Shared Outdoor Pool...
    • Satellite TV
    • Refrigerator
    • Air Conditioning
    • Grill
    • Deck
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The spacious living room/dining room features a with large flat screen TV and DVD player. Living room French doors open up into the private deck which features outdoor seating and a Gas BBQ Grill, making your... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 31, 2014
    We had a wonderful time staying in Key West. The condo location was perfect. We walked everywhere. The beds were comfortable, and although the kitchen is very small, it was...
    4 of 5 stars Reviewed March 12, 2014
    This place is a very nice place to stay. Key West Vacation Rentals are very helpful and easy to reach. The location is perfect just 5 minutes walk to Duval Street and 15 min to...
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    4.5 of 5 stars (48) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4
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    • Patio
    • Hot Tub
    • Grill
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Part of the Nightly Group PALM GARDENS Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details. Osprey's Nest is an upstairs spacious unit at 905 White Street. The original Dade County pine walls have... View all property information
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed May 19, 2015
    they advertised this with a hot tub but it was broken when we arrived,and was not repaired until our last day there.told them about it when we arrived and they seemed unaware,and...
    3 of 5 stars Reviewed November 11, 2014
    The Osprey Nest accommodation is very comfortable and pleasant. It's a bit of a hike from the action on Duval Street, which is good because it's in a quiet neighborhood, but a...
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    4.5 of 5 stars (22) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4
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    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Patio
    • DVD Player
    • Internet Access
    • Deck
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Elder access
    • x
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    About this property
    Located inside the Villas known as Old Town Garden Villas With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 30, 2015
    As good as the unit was and it really was its the people behind the organisation that make the difference ! I had stuffed up my original booking by 4 weeks, hey I'm old, it's...
    5 of 5 stars Reviewed December 23, 2014
    Trying to pick out a vacation rental in Key West is like finding a needle in a haystack. You just never know what you are going to get. I did a lot of research before we settled...
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    4.5 of 5 stars (18) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 7
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    • Deck
    • Shared Outdoor Pool...
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    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Linens Provided
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    Short walk to Fort Zachary State Park and South Beach! This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town.... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 19, 2015
    Great place for 4 people only. The 2 pullout Couch beds were so wore out my 3 sons had horrible nights sleeps the 5 nights there. I read a review that the pullouts were bad but...
    5 of 5 stars Reviewed September 27, 2014
    Very, very nice! Comfortable and clean too. Only complaint is the roosters next door crowing early in the morning. Very audible on the master bedroom side of the unit.
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    4.5 of 5 stars (25) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Deck
    • Balcony
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and... View all property information
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    Key West, Florida Keys 33040
    2 of 5 stars Reviewed August 12, 2015
    This condo is in a great location. The condo itself needs to be updated. Furniture was old and worn. Many area on walls had cracked and peeling paint. The chest that the TV in...
    5 of 5 stars Reviewed January 14, 2015
    My husband and I stayed here with another couple and it was great! Great location, lots of room! There is definitely a master suite and a second bedroom but both rooms have...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Balcony
    • Hot Tub
    • Linens Provided
    • Air Conditioning
    • Shared Outdoor Pool...
    • Refrigerator
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm 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 and bask... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 stars (48) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Hot Tub
    • Satellite TV
    • Patio
    • Shared Outdoor Pool...
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    Inside, you will find all of the comforts of home and This two-story 1880's Cigar Maker's Cottage has been completely renovated and has a living room with 42' flat screen TV/DVD, Queen sleeper sofa, kitchen with dishwasher, dining room and bath (with outdoor shower) on the ground floor.... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed August 1, 2015
    Amazing accommodation, plenty of room, kept wonderfully clean by excellent maid service.. It's very close to Duvall street which was great but downside is that it was a bit noisy...
    4 of 5 stars Reviewed February 12, 2015
    Family House is in a great location -we could walk everywhere we wanted to go in Key West. We were on vacation with 6 adults. The major downside to this house is that the sofa bed...
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    4.5 of 5 stars (10) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Private Outdoor...
    • Refrigerator
    • Patio
    • Air Conditioning
    • Grill
    • Satellite TV
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 28, 2015
    Helen's Hideaway is a great little hideaway in Key West. It is very private and has parking which is an added bonus. Inside the house it was clean and we had maid service every...
    5 of 5 stars Reviewed November 13, 2014
    Loved this place.It's exactly as pictured online. Loved the heated pool and the tropical feel of the pool area.Great location. Our only complaints: pull out couch needs replacing...
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    4 of 5 stars (9) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6
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    • Satellite TV
    • Deck
    • Air Conditioning
    • Refrigerator
    • Grill
    • Shared Outdoor Pool...
    • Internet Access
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location. Enjoy nearby... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 15, 2015
    I stayed here with four of my friends and the location was wonderful close to restaurants close to clubs and only a half a block off of Duval. this is a wonderful place and I...
    5 of 5 stars Reviewed July 4, 2009
    My husband and I stayed here with my parents and had a really wonderful time. The house was adorable, clean and had everything we needed. It was close to all the action on Duval...
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    4 of 5 stars (38) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4
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    • Air Conditioning
    • Deck
    • Patio
    • Satellite TV
    • DVD Player
    • Internet Access
    • Hot Tub
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    Overlooking the gardens and lily pond, the entrance to this spacious unit is through a totally enclosed private decked courtyard with a 4-person spa, table and chairs. Inside this spacious unit you will find a living room with cathedral ceilings, 56” TV, A/C, stereo, queen sleeper sofa and fabulous... View all property information
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    Key West, Florida Keys 33040
    1 of 5 stars Reviewed August 13, 2015
    It's a shame Key West Vacation Rentals has scum representing their company. I will NEVER even think about staying with KWVR again. Although we did feel a smidgen of relief to...
    5 of 5 stars Reviewed January 26, 2015
    Wonderful property, great location for walking around Key West. Rooftop deck for morning coffee and enclosed patio. Parking is at a premium, especially around the property, so...
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    1 Bedroom, 1 Bathroom, Sleeps 4
    Overview Make Inquiry
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    • Linens Provided
    • Air Conditioning
    • Satellite TV
    • Terrace
    • Internet Access
    • Balcony
    • Parking
    • Refrigerator
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-style complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 stars (11) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Satellite TV
    • Refrigerator
    • Grill
    • Deck
    • Air Conditioning
    • Internet Access
    • Private Outdoor...
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom... View all property information
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed May 5, 2015
    This home is beautiful but a little TLC goes a long way. It would be nice if someone would give the outside pool area a good scrubbing. I'm not new to renting homes in KW and this...
    5 of 5 stars Reviewed March 11, 2015
    Excellent location, between Duvall and Simonton. Home is decorated nice. Very clean. We had two couples and had plenty of privacy. The pool is so nice and it was heated! Daily...
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    4.5 of 5 stars (28) Very good
    Studio, 1 Bathroom, Sleeps 2
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    • Parking
    • Grill
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Patio
    • Linens Provided
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    The Truman Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 13, 2015
    Can't say enough about this place. Will never stay at another location in Key West. Staff was kind and helpful. Felt like this place was my own home, very cozy. Highly recommend.
    3 of 5 stars Reviewed October 29, 2014
    Late reservation so I couldn't be picky. Bed mattress needs to be replaced. Nighttime security light didn't work. Pool nice. Clean full kitchen
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    4.5 of 5 stars (19) Very good
    Studio, 1 Bathroom, Sleeps 2
    other travelers have booked this property
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    • Grill
    • Air Conditioning
    • Internet Access
    • Refrigerator
    • Deck
    • Hot Tub
    • Patio
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Part of 4 exclusive units at Abbey Road, renovated January, 2010, this suite is at 918-920 Center Street. Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft... View all property information
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed August 18, 2015
    Starr Suites was located in a great place close to everything. The Suites need a little work, they are clean but they need some items repaired and replaced. The Hot tub is worn...
    5 of 5 stars Reviewed July 14, 2015
    We stayed in the Starr suite of the Abbey Road complex. It was well stocked, with all the amenities you might need. It was updated recently I believe so everything felt new and...
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    5 of 5 stars (2) Excellent
    Studio, 1 Bathroom, Sleeps 4
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    • Air Conditioning
    • Grill
    • Satellite TV
    • Patio
    • Ceiling Fans
    • Internet Access
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of Southernmost Sanctuary Suites The Osprey Suite (Formerly the Osprey Suite) - Located in the Garden at the Southernmost Studios, the Osprey Suite is the perfect island getaway. Located within walking distance to all of the charms in Old Town you'll never want to leave! The Osprey has a... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 25, 2015
    This place was perfect for our vacation needs. It was close to everything, and the places a bit further away totally doable by renting bikes for the week. We cooked some meals...
    5 of 5 stars Reviewed August 28, 2014
    This was a last minute booking for us.. we had no idea what type of room we would be getting. Boy were we surprised! The gate is a little hard to find at first and you begin to...
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    1 / 41
    3 Bedrooms, 4 Bathrooms, Sleeps 8
    Overview Make Inquiry
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    • Private Outdoor...
    • Air Conditioning
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    • Internet Access
    • Linens Provided
    • Patio
    • Balcony
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Due to licensing restrictions, this property has a minimum stay of 28 nights. Aqua Pearl Crest is a completely remodeled 3 bed 3.5 bath home with a private pool & outdoor shower. All 3 bedrooms have bathrooms en suite. Located in the White St Gallery district in 'mid-town.' Additional amenities... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (2) Excellent
    Studio, 1 Bathroom, Sleeps 4
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    • Patio
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    • Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Part of Southernmost Sanctuary Suites The Ibis Suite is located at The Sanctuary in Old Town key West, Only steps to the action, this studio suite has all the comforts of home but surrounds you in island style! Lush gardens surround the Jacuzzi and the calm atmosphere is exactly what you'll need... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 2, 2015
    My friends and I stayed at Ibis this past January (all in our mid 20's). I thought I reviewed this property then, but apparently I did not. It was our first trip to Key West and...
    5 of 5 stars Reviewed October 29, 2014
    We have stayed in this lodging five times. It is very clean and service is excellent and friendly. The location is secluded and especially quiet.
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    $788
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    4 of 5 stars (1) Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 12
    other travelers have booked this property
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    Amenities & Details
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located at 729 Whitehead St, 'Southern Palms' is the group property consisting of the following homes Coconut Palm formerly Island Oasis Traveler's Palm formerly Palm Isle Royal Palm formerly Little Palm which can all be booked individually. All together, these three units have 5 separate... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 11, 2015
    We took over the whole compound with three generations of our family - my family and 4 month old twins in the attic suite, my sister's family and the grandparents on the first...
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    $408
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    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Amenities & Details
    • Ceiling Fans
    • Hairdryer
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of Southern Palms COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been... View all property information
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    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed June 15, 2015
    My husband and I stayed here with 2 other couples. The location was absolutely perfect for walking or biking to anywhere on the island. The pool and outdoor area were also...
    5 of 5 stars Reviewed July 29, 2014
    This house was awesome! Good location and very appropriate for what we used it for (bachelor party). Very nice Pool and outdoor area at a great price. The lease management...
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    $178
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    4.5 of 5 stars (5) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6
    other travelers have booked this property
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    Overview Reviews (5)
    Amenities & Details
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Part of TROPICAL VILLAGE Tropical Hideaway - Lush gardens surround this lovingly restored two-story vacation house. This downstairs rental cottage has one bedroom with full bath and features a living room with queen sleeper-sofa, cable TV, DVD, stereo with CD player, and wireless internet. The... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 21, 2015
    We booked this rental through Flipkey. The pictures didn't really show how nice it is. It's not the Ritz, as the other review says, but really very nice. Good kitchen with pots...
    4 of 5 stars Reviewed May 19, 2015
    Don't expect the Ritz Carlton, it's Key West, as long as you understand that you will love it. Great location, pool is nice, unit had everything we needed. We took 4 adults in the...
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    $3,000
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    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Overview
    Amenities & Details
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Stove
    • Dishwasher
    • Linens Provided
    • Terrace
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities... View all property information
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    Location Information
    Key West, Florida Keys 33040