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Rentals with Pool 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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    5 of 5 stars (6) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    4 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    4.5 of 5 stars (11) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    5 of 5 stars (18) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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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
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    Key West, Florida Keys 33040
    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...
    5 of 5 stars Reviewed April 5, 2015
    Great old house with lots of character in the perfect location. Very clean, comfortable beds, and a great pool area. Had one minor issue that management fixed for us right away...
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    1 / 17
    5 of 5 stars (14) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    About this property
    Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and convience with new furnitire,... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 10, 2015
    Had a fantastic holiday in the Bimini Suite. It was clean, well decorated and probably had the most comfy bed I've ever slept in whilst away from home. The garden area was lovely...
    5 of 5 stars Reviewed March 17, 2015
    Stayed in the Bimini Suite with 2 friends . My wife made the reservations and dealt directly with Evelyn and David who were always reachable and friendly . You will not regret...
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    4.5 of 5 stars (8) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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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
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    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 / 26
    5 of 5 stars (23) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 5, 2015
    We scheduled our vacation with Jim and Joanne at Casa Del Sol and experienced a no hassle application. Our friendly hosts gave us all the information we needed to enjoy ourselves...
    5 of 5 stars Reviewed April 29, 2015
    Both my wife and I along with friends, stayed here. We had all the comforts of home. Owners were very accommadating, and thought of everything a renter would need. Wifi was...
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    4 of 5 stars (13) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Balcony
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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
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 30, 2015
    I traveled with my wife and 3 teen daughters for spring break. The condo was very nice with plenty of room for my family. The owner responded quickly to my Tripadvisor request and...
    4 of 5 stars Reviewed January 26, 2015
    We were pleasantly surprised with the condo. 2 separate bedrooms with 2 separate bathrooms and a kitchen and Living room. Bar stools for the kitchen bar. The condo was fully...
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    4.5 of 5 stars (8) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 25, 2015
    The people who work on property were very friendly. The main areas in the condo were very clean. The guest bath could have been cleaner. The kitchen had everything you would need...
    5 of 5 stars Reviewed March 5, 2015
    Located in a private condo complex, the unit we stayed in featured excellent amenities while also clean and well maintained. Location to old town and Duval will require...
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    4.5 of 5 stars (56) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    All new luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in NEW gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles from Duval St. and 2... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 3, 2015
    We loved our vacation! The house was in a great location, easily accessible to many of the best rated restaurants and local convenient stores. We LOVED the provided bikes and rode...
    5 of 5 stars Reviewed February 8, 2015
    Nice condo and only ten minutes from downtown. Judy was great to work with. Pool on property was enjoyed by our family.
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    5 of 5 stars (38) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • ?
    About this property
    This is a non-smoking condo (smoking on the balcony only) with that 'home away from home' appeal. My condo is reasonably priced and includes 1 king bed suite and 1 queen bed suite and a sofabed. All bed linens are provided. Wait there is more, 2 full baths, fully equipped kitchen (dine in/dine... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 1, 2015
    We were looking for a Key West property for two couples. This sure was a winner. The owner has not overlooked any need or want at this condo. Pam knows that many guest will be...
    5 of 5 stars Reviewed April 17, 2015
    This was our 3rd time staying at Pam's Condo and it felt like coming home. We LOVE this place! It is just the best having the kitchen. We caught fish on this trip and took them...
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    5 of 5 stars (14) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Ocean Views
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    About this property
    ************************************************************************************************* TAKE 20%+ OFF: -- Stay June 30 - July 3 (3 nights) and pay a reduced rate of $800 for all three nights instead of $1,020. -- Note, taxes and fees will be added to all rates.... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 7, 2014
    All the previous reviews are completely accurate. The location is quiet and peaceful but only minutes away (by car) from Duval Street. Inside, the condo is very well-appointed...
    5 of 5 stars Reviewed November 2, 2014
    This two bedroom condo has everything! Beautiful views, beautiful decor, incredibly clean and comfortable and equipped with everything you could want. We stayed for four days and...
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    5 of 5 stars (8) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Suitable for children
    • x
    • x
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    • Elder access
    • x
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    About this property
    What a unique way to spend time on the water. Its not a 5 star hotel but you will have a nice clean private chartered boat on the water. Get ready for a unique vacation that others will envy. Boat is a 2003 Beneteau 331, while the boat is dockside the marina has electricity, water and Internet.... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 18, 2015
    After a bit of a problem confirming the reservation, and no help from Trip Advisor, we arrived as scheduled on 5-15 and were met by Yanna who gave us a detailed tour of the boat...
    5 of 5 stars Reviewed March 6, 2015
    We spent 3 nights on this boat. James the owner was easy going and welcoming. He explained all we needed to know and was available by phone for any questions or concerns. Boat...
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    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • ?
    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
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    Key West, Florida Keys 33040
    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...
    5 of 5 stars Reviewed March 2, 2015
    My wife and I stayed in Shelley's Rooftop Hideaway for the entire month of February. It was fantastic, and we had a great time in Key West, due in no small part to the location...
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Gym
    • Hot Tub
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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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
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    Key West, Florida Keys 33040
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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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. This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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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
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    1 Bedroom / 2 Bathrooms / Sleeps 4
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    • Hot Tub
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    • Ocean Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • x
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    About this property
    WOW Oceanside Voted #1 Key West's Best Luxury Penthouse Marina/Condo/Pool Direct Oceanfront 1490 Sq Ft Condo, 3 Bedrooms, 2 Baths, (Sleeps 6) Oceanside Marina is one of the newest and one of the most prestigious communities offering breath taking water views and large, open units. The amenities... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 1, 2015
    My brother, mother and I and our spouses met up in Key West for a great vacation. This condo had plenty of space inside and out for 6 adults and was very comfortable. The deck...
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    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights*** MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO EXCEPTIONS Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light and bright... View all property information
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    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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    5 of 5 stars (3) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 6
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    • Pets allowed
    • Smoking allowed
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    About this property
    The Bonaire Suite is a bi-level suite decorated in a rich contemporary Palm Tree motif with two queen beds separated by a privacy curtain in the upstairs bedroom. The upstairs bath features a custom tumbled marble shower with glass door. Downstairs is a living room with sofa which converts to a... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 12, 2014
    My friend and I stayed at the Bonaire Suite and it was perfect! Cute bungalow style with plenty of room and amenities. So close to Duval, but you couldn't hear the roar, which...
    5 of 5 stars Reviewed June 12, 2014
    Perfect location! Half block from Duval street. Very cozy and well equipped and lovely pool area. I highly recommend this place.
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    4.5 of 5 stars (15) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Suitable for children
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    About this property
    Hidden from sight, among a colony of freestanding conch cottages, surrounded by lush tropical landscaping, you will find Hidden Treasure. Truly a treasure, it is the sister cottage of Island Style, owned by two sisters who share a passion for Key West. It features every high end amenity that you... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 6, 2015
    My wife and I rented here so our fiends could have their own space. It has 2 king bedrooms and 2 bathrooms with a full kitchen and living room. The real hidden treasure is that...
    5 of 5 stars Reviewed October 28, 2014
    Hidden Treasure is just that - a hidden treasure located off of Olivia street in The Colony. Lots of space including storage, a great outdoor area, a quiet secluded area and yet...
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    1 / 13
    4 of 5 stars (7) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    Resort style accommodations at an affordable price! Nestled among a colony of freestanding Conch style cottages, amidst lush tropical landscaping, sits Island Style, the sister cottage of Hidden Treasure. One of our most popular properties, it was renovated by two fabulously funky sisters who share... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 16, 2015
    Handy location for visiting the touristy (Hemingway house, Summer White House etc.) part of Key West. I received very good service when reporting a hardware problem in the...
    3 of 5 stars Reviewed February 11, 2015
    Clean, noisy window air conditioner, ants. Close to water. Staff pleasant and efficient. Musty smell but comfortable bed.
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    5 of 5 stars (10) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
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    About this property
    The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment with a king size bed in the bedroom and a queen size sleeper sofa in the living area. It accommodates 2-4 people. This property is rented by the week from Saturday to Saturday, it is not a hotel; it is a privately... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 14, 2014
    My wife and I stayed here from Oct 4th thru the 11th. The Condo is situated minutes away from the airport so it was a quick taxi ride. The grounds of the complex are well taken...
    5 of 5 stars Reviewed August 11, 2014
    My wife, 2 adult daughters, and I, stayed at Pam's La Brisa "Jungle Breeze" condo from August 2 - 9, 2014. The condo is located in a very safe and friendly gated community. Pam...
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    5 of 5 stars (7) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    Elegance and modern sophistication are apparent as you enter any one of these six newly complete townhomes conveniently located in a quiet Old Town neighborhood just three blocks from Duval Street. Construction was completed in 2007 on these beautiful villas that boast over 1700 sq ft. on two... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 14, 2015
    Strongly recommended for families, very nice backyard, private pool that you cannot get your children out of it, perfect location. But beware of mosquitos at the evening...
    5 of 5 stars Reviewed April 28, 2015
    I've been going to Key West for the past 10yrs, and have stayed all over the island. I was looking for a place for a long weekend (sometimes hard to come by in EYW bc lots of...
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    2 of 5 stars (1) Poor
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • ?
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    About this property
    The artist cottage is mainly used as a residence for visiting artist that are in town doing shows at my gallery. The cottage is very quiet and secluded with lots of privacy,situated amongst 100 year old trees and lush tropical foliage. The cottage was built in 1913 and is a true piece of old key... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms / 5 Bathrooms / Sleeps 4
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    About this property
    MONTHLY RENTAL ONLY Buoy's Backyard - an authentic Key West retreat in the historic district just a block from upper Duval (the quiet end), two blocks from Hemingway House, and three blocks to Southernmost Buoy and Beach. Brick driveway provides private gated parking for two cars. This home has... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    ******** Key West laws state that this property can only be rented out monthly******* This lovely home is in the Casa Marina District of Key West. It has a front porch, front balcony that the 2 smaller bedrooms have access to, a large patio by the heated private pool in the back yard, and a... View all property information
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    Key West, Florida Keys 33040
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    1 / 17
    4 of 5 stars (2) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    RENTAL RATES ARE NEGOTIABLE... Please contact us for current pricing and availability (we do not maintain calendars) In the event you, or any of your family, guests, or friends want to use the house at any time during the rental term, the rental rate would be the same. We do request that all... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 11, 2014
    This property is lovely. With the large main house and several small cottages,it would be great for family reunions. The pool, jacuzzis and landscaping are all beautifully...
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    5 of 5 stars (30) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is oceanfront with an Olympic... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 7, 2015
    Our family enjoyed this well stocked condo. They provided bikes to ride to the beach along with beach towels, beach chairs, umbrella, and cooler. The covered secure parking was...
    5 of 5 stars Reviewed March 25, 2015
    The condo is very spacious, lots of room for everyone and in a great location. The owners left us some very helpful tips and ideas for what to do in Key West. The Condo was clean...
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    3 of 5 stars (1) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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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
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    Key West, Florida Keys 33040
    3 of 5 stars Reviewed September 3, 2013
    Our first night I was kept up until 4 AM by noisy you people and I love to hang and have fun but come on they were really poorly behaved. The following night Saturday of Labor Day...
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
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    About this property
    Located on a quiet residential street in the beautiful Key West neighborhood of Casa Marina, A Low Key Paradise has a beautiful open layout, with views of the large private patio and pool visible as soon as you enter. Guests can walk to nearby Higgs beach, and Higgs beach dog park— perfect for your... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed March 22, 2014
    A great condo. All the amenities. Covered parking, close to the pool. Easy access to downtown, either by car or taxi. Wonderful communication with the owner. First time for 4 of...
    5 of 5 stars Reviewed January 23, 2014
    The condo was fantastic. I was clean convenient and would recommend to anyone. This was exactly as described.
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    1 / 25
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Pets allowed
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    • x
    • x
    • x
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    • x
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    About this property
    This home has a unique pricing structure. While it can rent for less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial (25% off) Monthly Rental discounts. Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 7, 2011
    This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is first...
    5 of 5 stars Reviewed March 5, 2010
    The heated pool and lush backyard foliage were the draw to this well appointed home. Parking was a nightmare, the neighbor to the right facing the house was most unpleasant. A...
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    5 of 5 stars (16) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • x
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    About this property
    Experiance the laid back life of the tropics in this light and airy 1 bedroom, 1 bath private home. Located on a quiet lane in the heart of Old Town, The Key West Garden House features a large covered back porch, outdoor living and dining area, gas barbeque and heated pool in a lush tropical... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 24, 2015
    The Key West Garden House is amazing. It is walkable to any location in Old Town and serves as a nice respite for down time. Susan was incredibly helpful with places to eat and...
    5 of 5 stars Reviewed November 23, 2014
    This house is in the most perfect location to enjoy Key West. Right in the historic district, close enough to walk anywhere, yet on a quiet side street that felt miles away form...
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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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
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    Key West, Florida Keys 33040
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    $2,225
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    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Ocean Views
    • Pool Table
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    • x
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    About this property
    28 DAY MINIMUM STAY IS MANDATED BY COUNTY LAW. PLEASE DO NOT SEND ENQUIRIES FOR SHORTER PERIODS!! Charted back in the 1800's, Shark Key was named by early explorers for its shark-like shape. This exclusive island boasts more than 2 miles of pristine shoreline, lush foliage, and a sparkling lagoon... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (44) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • x
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    • x
    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 24, 2015
    This trip to Key West was partially a college graduation present for our son and a family vacation. We had the most wonderful week and this was partially due to our stay at...
    5 of 5 stars Reviewed February 1, 2015
    All four of us were very happy with our stay ... very clean, beautiful, safe, conveinient location. Inside of the condo is as pictured and we couldn't have been more pleased with...
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    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    • ?
    • x
    • ?
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    • Elder access
    • x
    • ?
    About this property
    RENTAL RATES ARE NEGOTIABLE...Please contact us for current pricing and availability (we do not maintain calendars) In the event you, or any of your family, your guests, or your friends want to use the house at any time during the rental term, the rental rate would be the same. We do request that... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • ?
    • x
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    About this property
    Note, this is a monthly rental. 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 which... View all property information
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    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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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This stunning 2 bedroom/2 bath suite can accommodate up to 6 guests. Whether you want the hustle and bustle of Key West or just want to kick back and relax, this resort has it all. View all property information
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    Key West, Florida Keys 33040
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    $5,373
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    1 / 17
    5 of 5 stars (2) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 4
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    • x
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    About this property
    30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's 'Guestbook' column, this charming Old Town house has recently been completely and tastefully renovated by its owners. Located just across the street from Key West's historic city cemetery, truly a tourist attraction in our... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed August 8, 2013
    Don't reserve at Olivia Cottage . . . because you may prevent us from doing so. We have traveled the world to just about every 5 star hotel of interest, and Olivia Cottage is the...
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    4.5 of 5 stars (5) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • x
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    About this property
    Paradise found reservations must begin and end on a Saturday. You feel it the moment you arrive. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and grace of Old Key... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 2, 2015
    We loved our stay in Key West which was enhanced by the condo's location, views, lovely large heated pool and jacuzzi with views of Atlantic Ocean, our balcony with view of ocean...
    5 of 5 stars Reviewed May 30, 2014
    The vacation property is well worth the price. It's well maintain with beautiful views and perfect pool. Very spacious and quiet, perfect for a family. The condo is a 2 to 3...
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    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • x
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    Over 150 years ago, Key West was the future. In the mid 1800’s clipper ships from Europe and the Caribbean carved a trusted path of international commerce to the Key West seaport, and the island flourished in the Golden Age of Sail. With opportunistic wreckers and treacherous pirates in the wake of... View all property information
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    Key West, Florida Keys
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    $3,800
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    1 / 15
    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • x
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    About this property
    30 DAY MINIMUM RENTAL This cute cottage just off of Frances Street is a great hideaway, still in Old Town, but a good central location to get to the Historic seaport or new town. The light & airy combined living/dining area with its soft color toned furnishings, hardwood floors & many windows... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed February 6, 2013
    We really loved the cottage and did appreciate all the little extras our host had provided. The location couldn't have been more convenient. We rented bicycles but could have...
    5 of 5 stars Reviewed June 26, 2009
    I have rented the Angla Cottage for the past three seasons. The house is very comfortable with space for guests in a separate portion of thje house. Swimming pool is great, and...
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    5 of 5 stars (8) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • x
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    • x
    About this property
    Truman Annex Best Location in Town!! 2 Bedroom 1 Bath ground floor Shipyard Condo. This beautiful townhome sits on a private quiet walking lane and is just a 5 minute walk to downtown where you will find Key West's famous bars and shopping. Also a 10 minute walk to Ft. Zachary Taylor, our... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 23, 2015
    While the Artist Cottage was not available, the owner had another Shipyard condo that was perfect for us. The property is nicely maintained, the pool clean and warm, and the...
    5 of 5 stars Reviewed June 29, 2014
    Wonderful location was able to walk to experience Key West. Something for everyone to enjoy with 2 older teenagers. Did something every day but was very relaxing, never felt...
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    From
    $510
    / Night
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    1 / 21
    5 of 5 stars (4) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Chick-A-Pea’s Cottage: Located in the gallery district of Key West. The house is steps off of Duval St. near Hemmingway’s house, the Southernmost Point, the Butterfly Museum and great shops, restaurants and bars . The location is quiet & private… yet in the heart of key west The house is a... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 12, 2014
    My family and fiance stayed at Chick a pea this past may. Todd was wonderful during all of the communication phases, booking and getting into the property. Upon arrival Todd...
    5 of 5 stars Reviewed May 20, 2014
    My husband and another couple went for a week of relaxation. This was the perfect home with all the amenities. The pool and outdoor sitting area is where we spent most of our...
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    From
    $1,085
    / Week
    Payment Protection
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    1 / 26
    5 of 5 stars (4) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The Shipyard is 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... View all property information
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    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed January 7, 2015
    We have been going to Key West for the past 15 years and we always stay at Truman Annex. We have been many times throughout the year but in the past six years we have been going...
    5 of 5 stars Reviewed October 24, 2014
    I visit Key West often (twice a year if I can). Over the past couple years, I've been booking exclusively with Key West Vacation Rentals. They have wonderful properties available...
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    From
    $600
    / Night
    View Details
    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered... View all property information
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    Location Information
    Key West, Florida Keys 33040