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Rentals with Pool in Key West, FL

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    $349
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    1 / 18
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    $270
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    1 / 15
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    1 / 20
    4 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    4.5 of 5 stars (10) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable... View all property information
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    5 of 5 stars Reviewed February 5, 2015
    Easy walking to Duval St., waterfront and many Key West attractions. Plenty of room for three couples. Pool area is great! Beds are comfortable. Good value.
    5 of 5 stars Reviewed January 25, 2015
    This place far exceeded our expectations and was quite cozy. We weren't aware of the pool until we arrived so seeing such a great perk just added to a wonderful experience.
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    1 / 17
    5 of 5 stars (13) 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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    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...
    4 of 5 stars Reviewed March 13, 2015
    We stayed in the Bimini Suite for two nights in early March. It was perfect size for us - two retired couples. The owner happened to be there working on the roof and was very...
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    1 / 5
    3 of 5 stars (1) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Suitable for children
    • x
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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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    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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    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • 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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    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 / 14
    5 of 5 stars (15) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
    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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    5 of 5 stars Reviewed February 2, 2015
    We stayed here for a week, for our destination wedding. We were able to entertain all of our wedding guests from out of town. Perfect size for our needs; great front porch...
    5 of 5 stars Reviewed November 18, 2014
    We were in key west playing music at a friend's wedding around the corner at old town manor. The Bahama House is perfect! it is close to everything, there's a beautiful pool...
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    1 / 8
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pool Table
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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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    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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    4 of 5 stars (6) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    • x
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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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    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.
    4 of 5 stars Reviewed July 9, 2014
    Nice little cottage with private patio, located adjacent to the pool. Cottage was clean and well maintained, and had a full kitchen with all the amenities. It was walking...
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    1 / 10
    5 of 5 stars (3) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 6
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    • 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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    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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    $495
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    1 / 25
    5 of 5 stars (5) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • ?
    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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    5 of 5 stars Reviewed April 17, 2014
    This house was gorgeous. Clean, updated and simply beautiful. It also had everything we needed...hair dryers, ironing board, laundry room, etc. If you are looking for something...
    5 of 5 stars Reviewed October 9, 2013
    Six women stayed in this beautiful townhome for three nights for a girls getaway. We would normally have booked hotel rooms, but staying here far exceeded our expectations and we...
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    4 of 5 stars (12) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    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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    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...
    3 of 5 stars Reviewed November 16, 2014
    This is a nice 2 bed 2 bath condo, clean, comfortable, and nicely decorated. The pool and hot tub in this small resort were very nice. Kitchen was adequate with new pans - I...
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    5 of 5 stars (28) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
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    • Satellite TV
    • Sauna
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    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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    5 of 5 stars Reviewed March 16, 2015
    This Condo was perfect for my friends and I. It had all the comfort of home right down to small details. Everything in the kitchen you could need. The pool area is beautiful...
    5 of 5 stars Reviewed December 15, 2014
    We stayed in the condo for four nights with five people and we were all pleasantly surprised to see how well equipped the condo was. The condo has two bedrooms and though we could...
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    4.5 of 5 stars (8) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    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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    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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    5 of 5 stars (35) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Hot Tub
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    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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    5 of 5 stars Reviewed January 8, 2015
    We have been going to Key West for 8-9 day stays for 20 years. Stayed in lots of rentals but this has been by far the best accomadations we've have had. It had the comforting...
    5 of 5 stars Reviewed December 31, 2014
    Fanatastic location. Perfectly appointed with every amenity. Immaculate. Pool was wonderful. Pam was very helpful. We had an amazing holiday away from home in a Pam's...
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    5 of 5 stars (14) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Internet Access
    • Ocean Views
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
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    • Elder access
    About this property
    ************************************************************************************************* TAKE 25% OFF: -- Stay April 4-6 (2 nights) and pay a reduced rate of $765 for both nights instead of $1,025. -- Note, taxes and fees will be added to all rates.... View all property information
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    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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    4.5 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Dryer
    • Grill
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    • Satellite TV
    • Shared Outdoor Pool...
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    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    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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    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...
    4 of 5 stars Reviewed September 11, 2014
    Great location for walking and biking all around Key West. Close to restaurants and attractions. Limited Parking.
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    5 of 5 stars (5) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
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    About this property
    The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an... View all property information
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    5 of 5 stars Reviewed January 28, 2015
    Loved the house, pool, location. Beds were very comfortable. Loved everything about it. Already have friends asking about rental.
    5 of 5 stars Reviewed January 15, 2015
    We were so pleased with this accommodation. The location is fantastic for enjoying all that Duval Street has to offer. Would recommend this place to anyone. Just sorry our...
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Balcony
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    • Dryer
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small boats on trailer allowed.... View all property information
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    2 of 5 stars (1) Poor
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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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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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
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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... View all property information
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    1 Bedroom / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Hot Tub
    • Internet Access
    • Ocean Views
    • Safe
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    • Pets allowed
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    • 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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    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge... View all property information
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    4.5 of 5 stars (8) Very good
    1 Bedroom / 4 Bathrooms / Sleeps 2
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    • Air Conditioning
    • Dishwasher
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    • Pool Table
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    About this property
    Beautiful New large modern Home on very quiet street . Location , Location Location ! Share .5 Star $2.4m Home in Old Town Key West.. Own fully furnished bedroom with Queen size bed for 1 - 2 max ( see photos ) with 32' flat screen TV. and 2 french doors leading onto private balcony... View all property information
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    5 of 5 stars Reviewed March 9, 2015
    We stayed here 3 nights/4 days. Don was a very gracious host and made our time sitting around the pool very enjoyable. He always knew the appropriate music to play for us. I...
    5 of 5 stars Reviewed March 6, 2015
    Wonderful house with a lovely pool. Just off Duval yet nice and quiet. Leave your car parked and walk everywhere. You couldn't ask for a better host than Donal. We hope to come...
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    5 of 5 stars (21) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    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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    5 of 5 stars Reviewed January 29, 2015
    We stayed at casa del sol thanksgiving week, Nov 2014. What a great place to stay. Jim is awesome n pleasant to deal with. Having 2 teenagers, 18/16, they could walk...
    5 of 5 stars Reviewed January 18, 2015
    Recently spent one week at Casa del Sol. This rental was in a perfect location, wonderful amenities, tastefully decorated and as neat as a pin. The Truman Annex location was...
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    4.5 of 5 stars (56) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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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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    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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    2 Bedrooms / 5 Bathrooms / Sleeps 4
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    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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    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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    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
    2 Bedrooms / 1 Bathroom / Sleeps 4
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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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    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...
    5 of 5 stars Reviewed March 3, 2015
    For sail boat minded people this is perfect : comfortable boat, beautiful yacht club and possibility to enjoy environment with kayaks. After visit of crowded key west it's very...
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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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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    One of the very few & one of the largest oceanfront suites in Key West OCEANFRONT… there is nothing like it. To me, it means being directly on the shoreline with nothing between me and the sensation of the ocean. Totally different from ocean view, which could mean having to lean over your balcony... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    5 of 5 stars (44) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    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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    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    PLEASE DO NOT SUBMIT RESERVATIONS FOR LESS THAN 28 DAYS. THANK YOU! Enjoy a stay in our Florida house on Shark Key, minutes from Key West surrounded by turquoise waters, white sandy beaches, lush vegetation and spicy aromas. Shark Key is a peninsula that extends from US Route 1 into Florida Bay... View all property information
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    3 of 5 stars (2) Average
    3 Bedrooms / 4 Bathrooms / Sleeps 10
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    1207 Heaven on Florida is Key West Casual at it's best! Decorated by a world travelling, gallery Curator/Artist/Entrepreneur- the place is a refreshing twist of elegant, sophisticated & funky with local & international art, contemporary & mid-century modern decor & comfort. The layout includes 2... View all property information
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    2 of 5 stars Reviewed March 18, 2015
    I invited a group of friends to go to Key West..it's a last-minute booking and we book this place because the photos look so great! But I can assure you after arriving at this...
    4 of 5 stars Reviewed February 21, 2015
    Stayed for 9 nights in Feb. 2015. Traveled with spouse and another couple. Plenty of room for 3 couples at this house. Location was a little farther than we thought from devall...
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    5 of 5 stars (16) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
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    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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    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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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water's edge has been quintessentially transformed into Old Town Key West's most... View all property information
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    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    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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    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    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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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    5 of 5 stars (2) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 4
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    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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    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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    5 Bedrooms / 6 Bathrooms / Sleeps 12
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    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa... View all property information
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    5 of 5 stars (8) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    THIS PROPERTY IS A MONTHLY ONLY RENTAL Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining, you are steps away from... View all property information
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    4 of 5 stars Reviewed April 23, 2012
    We've stayed in 4 different vacation rentals for a month or more at a time, and I think we enjoyed Casa Manana the best. Lots of character, great location, friendly cats and...
    5 of 5 stars Reviewed July 2, 2011
    The home was wonderful & the perfect size for our family. It was close to everything & we enjoyed the nearby church bells while sitting by the pool. We were surprised however...
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    4 of 5 stars (30) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    Thoughtfully restored, Havana Lane, hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery this classic conch cottage, embodies the essence of rustic charm while offering modern amenities and... View all property information
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    5 of 5 stars Reviewed April 18, 2014
    This house will not be for everyone. It's rustic, and advertised as such. If you like new, bright, cookie cutter houses with granite countertops and pillowtop mattresses, with...
    5 of 5 stars Reviewed August 22, 2012
    The house was even more perfect than we'd imagined. It perfectly captured the Key West charm that we wanted while visiting. The backyard was amazing and we enjoyed the pool and...
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    4.5 of 5 stars (43) Very good
    Studio / 1 Bathroom / Sleeps 2
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    Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West... View all property information
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    4 of 5 stars Reviewed March 6, 2015
    My husband and I have made numerous trips to Key West and have usually stayed at larger hotels but this time we wanted to try something different so we booked the Bali Hideaway...
    5 of 5 stars Reviewed March 13, 2013
    This is the first time my husband and I have been to Key West and this was the perfect spot to stay. It was just the right size for a romantic getaway. Even though we were only a...
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    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    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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    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 (2) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Wheelchair access
    • Elder access
    • x
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    About this property
    This beautiful home offers you contemporary luxury combined with exquisite historical charm of Old Town Key West. The open and spacious downstairs floorplan has an abundance of natural light and opens onto a fabulous pool area with an expansive deck. Entertaining your family and friends is... View all property information
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    5 of 5 stars Reviewed November 3, 2013
    I was there with my husband. The place is so beautiful. It has everything you need for a great holiday. The house is spacious. The pool/garden area is very big and private. The...
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