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Rentals for Seniors in Key West, FL

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    1 / 17
    4.5 of 5 bubbles (30) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 14
    5 of 5 bubbles (23) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 39
    5 of 5 bubbles (36) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 6
    4 of 5 bubbles (3) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
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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 bubbles Reviewed September 18, 2015
    I would definitely stay here again! It was a great trip with a lot of memories made thanks to the wonderful owner of this apartment. It was the perfect space in the best location...
    4 of 5 bubbles Reviewed May 25, 2015
    This room had all the comforts of home. A bit dated, but very clean. A bit of a drive to Duvall though. About a 10-12 min cab ride. We were there with 6 people and the cab drivers...
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    1 / 12
    4.5 of 5 bubbles (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed October 25, 2016
    Really enjoyed my stayed, I Will definitely will stay hear again, everything was just as expected, location was great, owner was fantastic and very helpful, apartment was very...
    4 of 5 bubbles Reviewed August 17, 2016
    Two bedroom, two bathroom condo suite with patio, across the street from the water. Each bathroom is connected to a bedroom, with the master bedroom having private access, of...
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    1 / 15
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed March 9, 2016
    First time renting from Trip Advisor. The entire process went very smooth & would definitely recommend it. Stayed at this location for a week with spouse and another couple...
    5 of 5 bubbles Reviewed March 18, 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
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    1 / 23
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed January 26, 2016
    This great rental was even better than advertised. It offered total peace and privacy with the private back yard and pool, and cottage with a second bedroom and outdoor shower...
    5 of 5 bubbles Reviewed January 18, 2016
    My husband and I stayed with friends at this beautiful home (Oasis lives up to its name). Our friends who we were traveling with had been to Key West many times, but this was our...
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    1 / 20
    4 of 5 bubbles (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Come down and take part in in Key West's many fishing tournaments! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family friendly condo in... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed February 10, 2014
    I hosted a bachelor/bachelorette party the weekend of Dec 28th and I stumbled on this space while i was searching. Everything on Duval was booked and around $1300-$1500 for 2...
    5 of 5 bubbles Reviewed October 25, 2013
    A very nice accommodation. Very well thought out and presented. Faultlessly clean and well maintained. Pauly was quite kind and took great pains to ensure our complete...
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    1 / 22
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    This beautiful motor yacht is available for your exquisite Key West vacation! . Huge Salon, Large galley, gorgeous teak throughout. One queen bedroom and one full bedroom with bathrooms for each one. Forward on the bow are 2 very comfortable loungers with pillows for relaxing. The upper deck is... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 32
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed November 12, 2016
    House was very clean and the owner was very helpful and responsive. I would definitely stay again and would highly recommend it to anyone going to key West !
    5 of 5 bubbles Reviewed August 30, 2016
    We loved every part of this rental. It was clean, not cluttered, great location, well-equipped, quiet and very comfortable. The pool was very nice and the community friendly...
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    1 / 22
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed October 24, 2016
    Fantastic. No other word describes it better. The view, the amenities, the layout of the condo...all fantastic. Owner is a very nice lady too. Very easy to deal with. Will...
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    1 / 10
    4 of 5 bubbles (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    About this property
    Over 100 miles from mainland Florida and the southernmost point in the United States, Key West has attracted numerous artists and writers, including Ernest Hemingway, Wallace Stevens, Ralph Ellison, Elizabeth Bishop, Tennessee Williams, Robert Frost, and James Merrill. At 410 Caroline Street is... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed November 19, 2016
    This place was very nice and cozy just steps away from duval . Perfect for a quiet get away for you and/or your spouse . I've stayed many places and this one was just right for...
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    1 / 17
    5 of 5 bubbles (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    The "SeaJay" at La Brisa is located in a gated community overlooking the Atlantic Ocean just steps away from Smathers Beach with it's pristine sand and palm trees. Directly across the street is Key West's longest sidewalk along the beautiful ocean for bike riding, jogging or walking. Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed March 8, 2016
    The condo was great, had all the amenities! Perfect location, right across from the beach, beautiful view! Plus it wasn't far from downtown.
    4 of 5 bubbles Reviewed July 19, 2015
    Myself, my husband, my sister and brother-in-law had visited Key West on a cruise and wanted to return for a week vacation. I rented this condo because of it's location to a...
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    1 / 27
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights***<BR><BR>MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS<BR><BR>Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed March 17, 2015
    Stayed here for 2 months while I was having my house remodeled and I was very pleased with the facilities and the unit. The condo has been nicely redone and very well stocked...
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    1 / 20
    3 of 5 bubbles (1) Average
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • Patio
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    • Mountain Views
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    • x
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    About this property
    This studio has been newly remodeled with no expense spared. Free street parking in front of property and plenty more spots in very close vicinity. This guest room is cozy (the size of a small hotel room, 10'X12.5') with a QUEEN size bed but is so much better than a hotel room. We provide high... View all property information
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    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed August 12, 2016
    The Room was clean and the kitchen a plus, however, it was very tight for 2 people. The only place to hang clothing is on the back of the shower door which hits the bed when...
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    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Hyatt Sunset Harbour Residence Club. *2016 Certificate of Excellence Winner TripAdvisor* **1 WEEK RENTAL 5/28/17 to 6/04/17**. Location, Location, Location. Private Balcony. 2 bedroom 2 bath. Full kitchen, dining table and living room includes sofa bed. Can accommodate up to six people . TV's... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Modern 2 bedroom/2 bath condo with nice size balcony overlooks the Atlantic Ocean. California king bed in Master Bedroom and twin beds in the guest bedroom that can be converted into a king bed. Living room sofa with queen sleeper. Nicely decorated with a Key West Flair. Full kitchen with all... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    5 of 5 bubbles (71) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This is a non-smoking condo (smoking on the balcony only) with that "home away from home" appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed December 2, 2016
    We couldn't wait to come back to Key West and stay here at Pam's condo. This place feels so welcoming and comfortable. The condo has a great view off the balcony. Everything you...
    5 of 5 bubbles Reviewed November 14, 2016
    Very nice condo! Very clean and comfortable! Would definitely rent it again if going to Key West. Nice location too!
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    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
    About this property
    Kali Zoi House – The Good Life in Old Town Key West Kali Zoi is Greek for “good life.” That's what you'll have when you book a stay in this large, classic conch style house in historical Old Town. This 1,960 square foot, 2 story house has all of the charm of a 19th century home but was... View all property information
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    Key West, Florida Keys 33040
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    1 / 14
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    This 4 bedroom 3 bath home is located in Key Haven (mile marker 5) Key West. Key Haven is a quiet neighborhood Great for boating, snorkeling, diving, fishing, biking, walking or just relaxing in the hammocks. Easy boating access to the Gulf and Atlantic (one canal from open water). Just 4 miles... View all property information
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    Key West, Florida Keys 33040
    1 / 12
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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 ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical... View all property information
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    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed November 28, 2016
    This property is very convenient to everything in Key West. We walk every day--we can go to the beach, the sunset, Duval, and all of the various attractions on foot. The...
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    1 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    This 2 bedroom, fully furnished condominium is located in the Truman Annex, a gated community of private homes and condominiums. Freshly painted and upgraded with custom bedspreads, new key west style furniture, all flat screen televisions, comfortable outdoor furniture, queen bed with two twin... View all property information
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    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
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    Key West, Florida Keys 33040
    1 / 9
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    1 bedroom with king bed. Living room with pull out sofa bed. 1 bath with jacuzzi tub and shower. Washer and dryer in unit. Balconies off of bedroom and living room with marina view. Stainless steel appliances. The Galleon has a heated pool with hot tub. A small private beach. Poolside tiki bar... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    4 of 5 bubbles (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed November 6, 2016
    Overall we were satisfied with our stay at this condo, but there were pros and cons. Pros: The layout was nice, almost like 2 separate hotel rooms joined by a shared kitchen...
    5 of 5 bubbles Reviewed July 14, 2016
    This condo was amazing. The service provided was excellent. I loved the location and it was just what i was looking for. Knowing we had a great place to stay made the trip even...
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    1 / 22
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach.<BR>This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed November 22, 2016
    Lovely clean condo with great views of the salt ponds. Fully equipped with everything you need. Great having a supermarket on site too.
    5 of 5 bubbles Reviewed February 15, 2016
    A clean, well maintained condo, everything in working order including the three flat screen TVs. We loved the balcony looking out over the salt ponds and could see Egrets and...
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    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    A great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million dollar homes that are... View all property information
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    Key West, Florida Keys 33040
    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Just one-half block from famous Duval Street, this turn of the century cigar makers cottage lies in the center of Old Town. Just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This KEY WEST HOUSE is just steps from restaurants, night life,... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    4 of 5 bubbles (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Smoking allowed
    • x
    About this property
    Mango Hideaway is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local as... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed July 28, 2016
    We had a great stay with Andrews Inn. We stayed in the Mango Hideaway.. Very quant and cozy cottage feel and super clean. The bed was so comfortable I felt like I was home...
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    1 / 17
    4 of 5 bubbles (1) Very good
    2 Bedrooms, 5 Bathrooms, Sleeps 6 | Quick View
    other traveler has booked this property
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    • Ocean Views
    • Shared Outdoor Pool...
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 bubbles 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 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Patio
    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    MONTHLY RENTAL ONLY This spacious 3 bedroom, 2 bath has all new stainless steel appliances and cabinets in kitchen, 15 ft. bar with wine cooler, new 55' flat screen in living room with cable TV. Large master bedroom with king size bed and French doors opening to pool deck plus 55' flat screen... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • x
    About this property
    This private ground floor waterfront home is located in the Key Haven subdivision of fine homes. Beautifully decorated with all new furniture, new flat screen televisions, new beds that includes two king size for extra comfort, large open living room with french doors invites in the tropical... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 bubbles (48) 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
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire Key West rental property has been decorated using art from the local galleries and artists. The theme is "Key West" from scenes around the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed September 28, 2016
    Just returned from a stay and this property exceeded our expectations. It was a great location in easy walking distance to everything on Duval. The unit was spotlessly clean and...
    5 of 5 bubbles Reviewed July 4, 2014
    Great Location to enjoy all Key West has to offer. CVS for stocking up on snacks, alcohol, basic groceries is right next door. It was great to have 2 baths upstairs and 1/2 down...
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    1 / 17
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Ocean Views
    • Patio
    • Grill
    • DVD Player
    • Housekeeping...
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    The Beautiful 42' Catamaran Calypso is a spacious Luxury Boat with all the latest Amenities. With 3 Cabins available... it sleeps 6 people comfortably. Each cabin has its own bathroom with all new faucets and electric flush toilets. Aboard Calypso you will find several places to lounge, sit back,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed yesterday
    Had a great 5 days of causing around, diving and paddle boarding. Captain Jon had all the great spots. Great food and we caught 1 large fish(forgot the name) but it was good...
    5 of 5 bubbles Reviewed yesterday
    Amazing cruise from Nassau to Staniel and back! Every detail was accounted for, the yacht is incredible, the team is great - what a weekend! Staniel Cay is the perfect vacation...
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    1 / 24
    4.5 of 5 bubbles (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
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    DUVAL BREEZE: Enjoy the great location of this beautiful 2 bedroom 2.5 bath vacation home key west located in the gated rooftop community of Duval Square on Duval Street, in the middle of the action. Steps away from fantastic restaurants, nightlife, entertainment, bars and shopping on Duval Street... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles 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 bubbles 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 / 24
    4 of 5 bubbles (29) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Balcony
    • Grill
    • Satellite TV
    • Terrace
    • Private Outdoor...
    • Hot Tub
    • Parking
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    PAPAYA PLACE pops with color! This great 2 bedroom 2 bath waterfront Key West rental condo at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve. Enjoy the peace and quiet of the tucked away balconies, far from the reaches of the world, allowing... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed August 27, 2016
    At night, the frogs in the bird preserve next door sang me to sleep. In the morning, the cooing of the doves awakened me. What a splendid, quiet place to rest and write. The...
    5 of 5 bubbles 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...
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    1 / 9
    5 of 5 bubbles (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
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    • 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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles 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...
    5 of 5 bubbles Reviewed May 28, 2013
    Hemingway's Retreat was more than we could have hoped for! The house was beautiful, the location was perfect, and the pool was awesome for our family. The owner was fantastic to...
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    1 / 12
    5 Bedrooms, 5 Bathrooms, Sleeps 14 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    • Satellite TV
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    • Private Outdoor...
    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    About this property
    While relaxing in the free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Upon entering the 3200+ square foot home, the spacious nature of the home is evident providing ample room for large groups. Around the back of the home, the large deck with... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    5 of 5 bubbles (1) Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    • Grill
    • Balcony
    • Satellite TV
    • Patio
    • Internet Access
    • Private Outdoor...
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Our unique property consists of 3 suites (a total of 7 bedrooms and 6 baths) with 2 sparkling lagoon style dipping pools in one compound in the luxurious Casa Marina area of Old Town Key West. We can accommodate groups up to 18 guests. The breakdown of the 3 suites which are being rented... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed February 16, 2014
    So our stay was Friday - Tuesday in January … We rented the Hemingway suite then added additional rooms … Love Love Love this place !! can not say enough about the owners / and...
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    1 / 28
    4.5 of 5 bubbles (2) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Internet Access
    • Balcony
    • DVD Player
    • Hot Tub
    • Parking
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed March 20, 2016
    Very nice condo. A little far from the action but totally enjoyed bike riding all around the island, with the bikes provided by John. John was a great owner helping and...
    5 of 5 bubbles 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 / 24
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    4 of 5 bubbles (13) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • 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 - This two bedroom, two bath condominium is located oceanfront in a gated community with a direct view of the Atlantic Ocean. Enjoy spectacular views from this waterfront rental condo in Key West of the sparkling blue-green waters from your private balcony while relaxing in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles 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 bubbles 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 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Well maintained townhouse in the Truman Annex of Key West. The house has a beautiful garden that you will enjoy. A short walk to Duval and Mallory Square. All quality furnishings. Margaret' s Park is the choice in Key West. Two master suites with private balconies. The house is fully equipped... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Secure Parking
    • Wi-Fi
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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. La Brisa is a two bedroom two bath condo on the third floor. The master bedroom has a king size bed with a walk in closet, a desk... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    4.5 of 5 bubbles (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 seaside 2 bedroom 2 bath condominium will provide the much needed escape to tranquility you need. Let ocean breezes gently lull you to sleep and summer sunshine wake you in the morning from balconies that wrap around the condo allowing access from... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles 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 bubbles 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 / 12
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Patio
    • Satellite TV
    • DVD Player
    • Balcony
    • Grill
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    The master bedroom has a queen sized bed with a feather mattress topper to experience a floating cloud effect. It has cable flat-screen TV, DVD/VCR, and a balcony where you can sit (take director's chairs from bedrooms) for morning coffee or evening cocktails. The customized closet has a set of... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (6) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Internet Access
    • Private Outdoor...
    • DVD Player
    • Satellite TV
    • Grill
    • Hot Tub
    • Parking
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    KEY WEST CROWN JEWEL -- We know that you will enjoy staying in our vacation rental condo Key West - our little bit of Paradise. This is a 2-bedroom, 2-bath, penthouse condominium with 1350 square feet of living space and vaulted ceilings. Enjoy absolutely breathtaking ocean views and the colors of... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed March 26, 2014
    We had the great honor of staying in this unit for a week in March. Our teenage daughter had her own bedroom and bath, which was wonderful. The entire condo is clean, well...
    5 of 5 bubbles Reviewed March 14, 2012
    Again thanks to Gale she does a great job and is easy to work with. Have already booked The Crown Jewel for next year and plan to do so for years to come. Thanks Mitch and...
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    1 / 24
    4 of 5 bubbles (5) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Terrace
    • Hot Tub
    • Shared Outdoor Pool...
    • Satellite TV
    • Parking
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    SPA ON DUVAL - Is a tropical two story, 2 bedroom 2.5 bath Old Town Key West condo located in the rooftop community of Duval Square where you only have to walk downstairs to great restaurants, speciality shops and the action of Duval Street. Spa On Duval is truly a Key West experience to enjoy!... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed April 10, 2014
    My family found this place amazingly comfortable and exactly what we needed. Our two teenagers loved the place. It was so nice and close to downtown one way, and up to the beach...
    3 of 5 bubbles Reviewed August 7, 2013
    Let me first write that we've stayed in the duval complex before in the havana hideaway unit( great unit!) Spa on duval was very clean, great location and equipped with everything...
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