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Rentals with Pools in Key West, FL

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    1 / 14
    4.5 of 5 stars (26) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 17
    5 of 5 stars (22) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 17
    5 of 5 stars (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 14
    5 of 5 stars (19) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 22, 2015
    Traveled to Key West with my sister and my Mom to celebrate Moms 85th birthday. The house was so close to everything we wanted to do and see. The grocer nearby was great, the...
    4 of 5 stars Reviewed May 2, 2015
    We stayed for three nights in April. Checked in Saturday, and as we were unloading our car owner came by to say hi and ask if we had any questions. She answered the few...
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    1 / 6
    4 of 5 stars (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 stars 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 stars 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 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 stars 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 stars 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 / 12
    4.5 of 5 stars (13) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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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
    4 of 5 stars Reviewed 1 week ago
    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...
    5 of 5 stars Reviewed July 17, 2016
    We LOVED this condo for our stay in Key West. The condo was very clean, spacious, absolutely adorable, and most importantly affordable! It was nice to have access to a pool and...
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    1 / 14
    5 of 5 stars (8) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • x
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    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 stars 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 stars 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 / 30
    5 of 5 stars (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
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    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 stars 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...
    5 of 5 stars Reviewed December 15, 2015
    My husband and I stayed here from 12/5-12/2015. Flip Flop was immaculate, perfectly located in Old Town Key West and well furnished. The owner took all of the steps to make...
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    1 / 14
    4.5 of 5 stars (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 stars 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 stars 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 / 15
    5 of 5 stars (4) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • ?
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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 stars 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 stars 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 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Sauna
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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
    1 / 24
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
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    • Pet-friendly
    • Child-friendly
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    • x
    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool<BR><BR>Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 14, 2016
    Condo was ideally located for all our activities. Very comfortable and enjoyable! Cindy was a pleasure to work with, can't wait to return to Tiki, Too!
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    1 / 15
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • 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
    1 / 44
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    If you have had your fill of hotels and the street scenes of downtown Key West and you don't want to spend another minute on a boat loaded with people but do want to get out on the water, then S/V Tortuga may be the perfect solution for you. Tortuga Sailing Adventures offers a unique, totally... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    Ocean Views from Every Balcony. Expect every Amenity from Hyatt. Come Relax by the water with a cool drink. Come visit Old Town Key West for the Sunset Celebration on Mallory Square while enjoying the entertainment, dining and shopping along Duvall Street. This historical city has much to see &... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. Our condos' at La Brisa are two bedrooms with two full bathrooms on the third floor. The master bedroom has a king size bed with a walk... View all property information
    Location Information
    Key West, Florida Keys 33040
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 8, 2014
    This is a wonderful conch house in Old Town, Key West. The house is just around the middle of Old Town, so you can walk or bike to the harbor, the ocean, and the great music at...
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    1 / 22
    4 of 5 stars (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 stars Reviewed 4 weeks ago
    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 stars 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 / 27
    5 of 5 stars (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 stars 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 / 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • ?
    About this property
    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping.... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Secure Parking
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    • Pet-friendly
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    • x
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    • x
    About this property
    Great for large groups - 6 bdrms, 3 bathrms, sleeps up to 14 adults, White Ibis Inn just 15/20 minutes drive from Key West. Sometimes we run a special discounted price from our White Ibis Inn. If you are interested to book our place, please let us know how many people in your group, any pets,... View all property information
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    Key West, Florida Keys 33040
    1 / 8
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Private Yard
    • Air Conditioning
    • Shared Yard
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    • Pet-friendly
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    • x
    • x
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    • x
    About this property
    <BR> KEY WEST VACATION CONDO RENTAL DESCRIPTION<BR><BR> Our beautiful deluxe one bedroom condo in Key West Florida on<BR>Southard Street is just blocks from the ocean and Duval street.<BR>Located in historic old town, the condo is enclosed in a beautiful<BR>garden on the ground floor. It is... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 24, 2015
    We've stayed in this condo multiple trips to Key West. It sets back from the street behind a locked gate and you can feel safe and secure in this quiet condo community which also...
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    1 / 17
    4 of 5 stars (1) Very good
    2 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
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    • 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
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed January 29, 2016
    I own at this hyatt timeshare. The units are spacious. Very clean and nice grounds. Only problem is away from downtown and car is needed. Hyatt working on new shuuttle service to...
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    1 / 27
    4 of 5 stars (13) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    About this property
    CORAL SUITE: 2 bedroom 3 bath townhome for 6 people, and your pet! Both bedrooms (ensuite) are on the 2nd floor of this stilt home. Master bedroom has a private balcony. Guest bedroom is roomy and private. The Murphy bed in the living room is sturdy and comfortable. Kitchen is equipped with all... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 10, 2014
    There were 4 in our group (family), and we had a lovely time! It was a bit difficult to find, especially for the pizza delivery man...lol Despite Tropical Storm Issac, we had a...
    5 of 5 stars Reviewed April 17, 2014
    I am a seasoned visitor to Key West. Over thirty visits thus far. This was the best way to spend a week on the island. Everything was superb. Nothing was out of place...
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    1 / 29
    4.5 of 5 stars (11) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    CORAL VILLA: A beautiful 3-bedroom townhome in the gated community of Coral Hammock. Just off U.S. 1, across from the golf course, and minutes from some of Key West locals' favorite restaurants, marinas, Smathers Beach and the airport. Fully equipped kitchen, HDTVs, WIFI and off-street parking for... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed April 10, 2014
    Rent this condo if you are looking for a place out of the fray but nonetheless close. It is 10 - 15 minutes to Duval Street, and very bikeable. Stock Island eateries (Roostica...
    4 of 5 stars Reviewed October 10, 2013
    A group of 7 of us stayed here for 4 days and it was a very nice time. There was a slight shortage of towels but there was a washer and dryer that was fast and easy to use in the...
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    1 / 11
    4.5 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars 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...
    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.
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    1 / 24
    4.5 of 5 stars (56) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • DVD Player
    • Balcony
    • Internet Access
    • Satellite TV
    • Parking
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    DUVAL BREEZE: 2 bedroom 2.5 bath townhome in Duval Square. 1st floor offers an open floor plan with a well stocked kitchen, spacious living room, dining room, half bath and French doors to your own private balcony. 2nd floor has 2 bedrooms with bath ensuite. Master bedroom has a private balcony.... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 6, 2015
    First off At Home in Key West is awesome. We have used them twice and never had any trouble at all. They are very prompt, courteous and a delight to deal with. The condo...
    5 of 5 stars Reviewed February 26, 2014
    Loved Duval Breeze! The house was bigger than the pictures depicted and it was so comfortable. Having not only towels and linens available but also basics like toilet paper and...
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    1 / 39
    4.5 of 5 stars (29) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Satellite TV
    • Grill
    • Internet Access
    • Balcony
    • Terrace
    • Hot Tub
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    4 PALMS: Located 4 palm trees from the ocean, this 2 bedroom 2 bath condominium with sleeper sofa, within minutes of the hectic lifestyle of downtown. Balconies run the length of this home offering fresh air and sunshine with ocean breezes wafting by. Condo offers street view; complex offers ocean... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 29, 2014
    With a short walk to the beaches, the awesome pool and hot tub, and quick drive to Duvall Street, this was the perfect place to stay! Our condo was so clean and spacious and we...
    5 of 5 stars Reviewed April 12, 2014
    We love the location next to the beach. The pool and hot tub were clean and a perfect temp. The rental was very clean and well equipped. We bought more toilet paper and could...
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    1 / 22
    4.5 of 5 stars (84) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Private Outdoor...
    • DVD Player
    • Grill
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    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    BAHAMA DREAMING: One Of At Home In Key West's Most Popular Rentals! Bahama Dreaming is a traditional 3-bedroom Conch cottage located just steps from Duval Street. With it's fantastic location and amenities this home offers it all. The main level has 2 bedrooms, one containing a comfy queen size... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 3 weeks ago
    My husband and I and his family stayed here July-August 2016. The house was clean and just perfect for us. The location was superb as Duval was steps away. It was a great location...
    4 of 5 stars Reviewed June 21, 2016
    We have just returned from our yearly girls trip to Key West. We are a group of 6 women in our late 50's (60's) who visit every year in June for a week of fun. First, let ,e...
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    1 / 21
    4 of 5 stars (4) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Internet Access
    • DVD Player
    • Private Outdoor...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    ***PLEASE CALL/EMAIL FOR AVAILABILITY AS WE DO NOT USE THE CALENDAR SHOWN*** CASA ROSA is a four bedroom, four bath classic "eyebrow" style home located in historic Old Town Key West. This home is just 1 block off Duval Street and a short walk to Harbor Walk & Mallory Square. Enjoy Simonton... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 11, 2016
    4 bed/4 bath older/historical home. Some of the rooms lacked storage space but they were clean and beds/bathrooms were good. Two good size bedrooms and the other two not much...
    5 of 5 stars Reviewed April 4, 2016
    I rarely get on sites to complete a review. However, I felt that this review needed to happen, as I was looking for current reviews of the property when we were looking for that...
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    1 / 23
    4 of 5 stars (19) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Grill
    • Satellite TV
    • Balcony
    • Internet Access
    • Shared Outdoor Pool...
    • Air Conditioning
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed December 15, 2015
    Could be a great place . Needs a good deep cleaning and friendlier and more helpful women working in the office. Was there for 4 days with kids in November with no pool heater...
    5 of 5 stars Reviewed July 18, 2013
    I used to live in Key West and have had friends stay here before. I was excited to see the new renovations they had done. The room was beautiful and clean and our stay was great...
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    1 / 26
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Terrace
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Washer
    • Patio
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Beautifully renovated duplex in Old Town. 2 bed/1.5 bath. Sleeps 4-6. There is a private stairway to apartment/loft upstairs. Upstairs unit is a massive 1100 sq ft with cathedral ceilings and loft (2nd bdrm). There is a king bed in the master, full bed in the loft and a pull-out sofa. Fully... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Private Outdoor...
    • Housekeeping...
    • Satellite TV
    • Air Conditioning
    • Patio
    • Washer
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    * This vacation home is available to rent on a monthly basis only * Dating all the way back to 1884, this delightful 3BR home is located in Bahama Village, part of Key West's prominent Old Town neighborhood. This single-family home is available to rent on a monthly basis. If you'd like more... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 stars (26) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Grill
    • Satellite TV
    • Terrace
    • Private Outdoor...
    • Balcony
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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 stars 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 stars 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 / 18
    4.5 of 5 stars (55) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • Satellite TV
    • Grill
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    TROPICAL DREAMING: This tropical 2-bedroom home with classic art features, hardwood floors, tall ceilings, new appliances, new furnishings and a true Key West feel. One block from Duval Street , it is close to restaurants, shops, galleries and clubs. The Atlantic Ocean is only 4 blocks away. The... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 21, 2015
    Very Nice! Photos are true to form. Needed a place we could bring our small dog. Perfect distance from Duval. Pool was small but we had only 4-6 max (plus the dog). Grilled a...
    4 of 5 stars Reviewed March 19, 2014
    We loved Tropical Dreaming! The location is excellent, just two blocks from Duval and a few blocks from South Beach and practically in walking distance to everything. The home is...
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    1 / 19
    4.5 of 5 stars (36) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
    • Internet Access
    • DVD Player
    • Terrace
    • Satellite TV
    • Balcony
    • Private Outdoor...
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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 stars 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 stars 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 / 22
    4.5 of 5 stars (25) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Grill
    • Balcony
    • Satellite TV
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed June 30, 2015
    This is our second time staying at Pelican Landing. Our group comes up yearly for the Swim Around Key West race and we love the penthouse suites where we can all stay together...
    5 of 5 stars Reviewed June 11, 2013
    Pleasantly surprised at the cleanliness of the unit. Check in time was limited to 1 hour time frame, not so convenient. Liked the fact that I could take my small dog along, but...
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    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Terrace
    • Satellite TV
    • Internet Access
    • Balcony
    • Private Outdoor...
    • Parking
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Easy Livin' - The name says it all! This lovely private home with pool in a secluded cul-de-sac in Truman Annex, a pristine gated community located in historic Old Town Key West is walking distance of anything you will want to do during your visit. The formal entrance of this vacation rental... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    4.5 of 5 stars (47) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Parking
    • Balcony
    • DVD Player
    • Shared Outdoor Pool...
    • Satellite TV
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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 stars 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...
    4 of 5 stars Reviewed December 5, 2013
    Very nice 2 bedroom 2 1/2 baths located in an excellent location. Walk right down to Duvall Street. Located at the quite end of Duvall. Great accomdations but a bit pricey.
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    1 / 15
    4.5 of 5 stars (40) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Satellite TV
    • Balcony
    • Shared Outdoor Pool...
    • Air Conditioning
    • Patio
    • Internet Access
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Great, popular, quiet townhouse in the well-liked Duval Square complex in the heart of Old Town. One off-street parking space per unit. Easy walking distance to all downtown attractions. Bank, convenience store, health club, hair salon and fine restaurants in the complex. Families are... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 3 weeks ago
    My family and I stayed for 6 days and had a great time. As it was very hot in Florida this time of year the location was great to stop for a quick snack and break. Centrally...
    5 of 5 stars Reviewed April 27, 2016
    We had a great time, the house was nice, but the dishwasher was broken on the bottom rack, the electrical outlet upstairs blew and they had to come fix it, the faucet in the...
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    1 / 27
    5 of 5 stars (52) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Private Outdoor...
    • Terrace
    • DVD Player
    • Parking
    • Balcony
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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 stars 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 stars 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 / 27
    4.5 of 5 stars (25) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    • Grill
    • Internet Access
    • Private Outdoor...
    • Balcony
    • Parking
    • Satellite TV
    • DVD Player
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    BAHAMA HOUSE: Conveniently located in the heart of Old Town 1/2 block from shops, restaurants and nightlife on Duval Street. 3 bedrooms with private baths on 3 floors. Main level with gourmet kitchen, dining area, half bath, and sitting room with a wall of French doors to the deck and private... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 13, 2015
    We spent Spring Break at the Bahama House and it was perfect for our group. We had 4 adults and 4 teens. Bedrooms were ideal, especially the upstairs room which could fit all...
    5 of 5 stars Reviewed April 3, 2015
    We had an incredible time at the Bahama House in Key West. We were in town for my sister's wedding and our party included my parents, my wife and two young children and my sister...
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    1 / 9
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Secure Parking
    • Private Yard
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Why stay in a cramped hotel when you can relax in a private, quiet, and peaceful 2-acre estate! We are now running an special discounted offer for the Fall of 2016 WHITE IBIS INN - LOCATED ONLY A 15 MINUTE DRIVE FROM KEY WEST OR THE WORLD-FAMOUS BAHIA HONDA BEACH. Sometimes we run a special... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4 of 5 stars (28) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Internet Access
    • Balcony
    • Grill
    • Satellite TV
    • Terrace
    • Private Outdoor...
    • Hot Tub
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    PAPAYA PLACE: 2 bedroom 2 bath condo at 1800 Atlantic Blvd. with garden view overlooking the nature preserve. Master bedroom with new king bed and bathroom ensuite; twin beds in guest bedroom with full bath across the hall. WIFI, unlimited long distance calls,3 flatscreen TVs and expanded cable... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 8, 2016
    My wife and I have been staying at Papaya place for years and it just gets better! The beautiful colors and homey touches are our favorite. It is always immaculate when we arrive...
    5 of 5 stars Reviewed May 26, 2016
    This very pretty and comfortable condo was in a great location - access to the beach, very close to the airport and a five minute cheap cab to Duval Street. The condo is very...
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    1 / 24
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • Satellite TV
    • Grill
    • Internet Access
    • Private Outdoor...
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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 stars 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 / 25
    4.5 of 5 stars (54) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • DVD Player
    • Private Outdoor...
    • Grill
    • Parking
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    AMELIA HOME - 2 bedroom 2.5 bath home with sparkling private pool only four blocks from the Atlantic Ocean and one block from Duval Street entertainment. Kitchen complete with everything to create a gourmet meal. Large open dining and living area. Lush garden with private pool that gives one a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 12, 2015
    What a great place to stay. Location is perfect. Everything you need is supplied. Decor and Landscaping were also wonderful. Already talking about next years stay. Nothing...
    5 of 5 stars Reviewed April 2, 2014
    Amelia Home was a great place to stay and experience Key West. The house is very clean and in excellent condition. The pool made the stay.The location is great. You can walk to...
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    1 / 26
    4 of 5 stars (13) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Hot Tub
    • Terrace
    • Balcony
    • Grill
    • Satellite TV
    • Internet Access
    • Private Outdoor...
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    BRISA DEL MAR - 2 bedroom, 2 bath condo located oceanfront with a direct view of Atlantic Ocean. Fully equipped kitchen, dining area, and living room that opens to a private balcony with unlimited ocean views. Master bedroom has a full bathroom ensuite and entry to a private balcony. Guest... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 18, 2015
    This condo was just what we wanted. It had everything we needed including beautiful views. The condo was clean and the beds comfortable. The pool was great and the hot tub was an...
    5 of 5 stars Reviewed January 8, 2014
    The condo at Barisa was perfect, lots of space and breath taking views every day. Everything you could possibly need was right there. Not far from old town and all the beaches...
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    1 / 31
    4.5 of 5 stars (25) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Grill
    • Satellite TV
    • Terrace
    • Private Outdoor...
    • DVD Player
    • Balcony
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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 stars 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 stars 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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