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Pet Friendly Holiday Rentals in Florida Keys, FL

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    1 / 33
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 24
    5 of 5 bubbles (2) Excellent
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    1 / 30
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 29
    5 of 5 bubbles (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Hot Tub
    • Satellite TV
    • Internet Access
    • Balcony
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM to 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 12 May 2016
    We're the type of people who like to be away from the massive partying, and this was the perfect location. Even though you always can't get away from it completely, we feel like...
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    1 / 30
    5 of 5 bubbles (7) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Washer
    • Hot Tub
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2,000 square feet on 2 levels with under cover parking. It is located in the... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 bubbles Reviewed 27 July 2016
    I stayed in this condo for a week with my 3 children (ages 12, 19, and 20) and a friend and her child (age 20). The condo was located near all that we wanted to explore in...
    5 of 5 bubbles Reviewed 23 November 2014
    Really enjoyed this home, clean,secure, owner answered all questions in a timely fashion. Highly recommended!
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    1 / 9
    4.5 of 5 bubbles (4) Very good
    Islamorada
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Secure Parking
    • Wi-Fi
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    • Pet-friendly
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    • ?
    About this property
    This wonderful room opens up into a garden with a water pond. It includes a/c, coffee maker, TV, free WiFi, heat, microwave, refrigerator, shared bath with one other couple. Pool on premises. Close proximity to the beach. Includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    3 of 5 bubbles Reviewed 18 December 2016
    Appealing features: Convenient location. The grounds were beautiful, with a little waterfall, trees, plants and interesting art around little sitting areas in the courtyard...
    5 of 5 bubbles Reviewed 26 May 2016
    I recommend this B&B to anyone who just wants a beautiful property to relax and enjoy the company of your significant other. The staff is very attentive and accommodating and the...
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    1 / 25
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Internet Access
    • Satellite TV
    • Terrace
    • Shared Outdoor Pool...
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 29
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Balcony
    • Hot Tub
    • Terrace
    • Satellite TV
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Shared Outdoor Pool...
    • Air Conditioning
    • Satellite TV
    • Hot Tub
    • Balcony
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (32) Very good
    Key West
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
    • Internet Access
    • Patio
    • Satellite TV
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    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! Andros Suite is a bi-level suite with a very spacious bedroom upstairs with... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 19 May 2016
    We loved our stay at the Andros Suite. The unit was very comfortable. They even had daily service who came in and cleaned and provided fresh towels (which was unexpected). The...
    4 of 5 bubbles Reviewed 1 February 2016
    This is the second time my husband and I have stayed at one if the units in the Villas. The location is fantastic - walk to the action on Duval or the beach. And the property...
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    1 / 41
    4.5 of 5 bubbles (23) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • DVD Player
    • Internet Access
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    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located inside the Villas known as Old Town Garden Villas With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 1 June 2016
    Secure, gated community. Each unit was part of a duplex/townhouse. Close to Duval Street without all the noise. Home was clean and very spacious. Tons of drawer space, decent...
    5 of 5 bubbles Reviewed 30 May 2015
    As good as the unit was and it really was its the people behind the organisation that make the difference ! I had stuffed up my original booking by 4 weeks, hey I'm old, it's...
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    1 / 33
    Key West
    1 Bedroom, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Duval Delight is a breathtaking, newly-renovated 2-story condo located at the historic "Cuban Club" on the "quieter" side of world famous Duval St. This high end vacation rental features a huge 55-inch flatscreen TV in the living room and all brand new furniture including a comfy, pull-out queen... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 34
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Satellite TV
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Duval Hideaway features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. Each of the queen bedrooms has a 24' LCD TV, spacious closets... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 35
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    5 of 5 bubbles (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Balcony
    • Satellite TV
    • Terrace
    • Internet Access
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    (Recently updated!) Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 5 January 2015
    You can book this place if you do not mind occassional airplanes landing and taking off. This is a great place with very friendly staff. The main center of the Island is 5-10...
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    1 / 27
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Satellite TV
    • Terrace
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 17
    4 of 5 bubbles (8) Very good
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Washer
    • Balcony
    • Shared Outdoor Pool...
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Top floor suite! Beautifully furnished condo overlooking the aqua-blue waters of the Gulf of Mexico! This 1,700 sq. ft. , custom decorated condominium offers a unique water vista from the living areas. The split floor plan provides privacy as the bedrooms are on each side of the living/dining area.... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 bubbles Reviewed 28 August 2016
    This was our second stay at this property. We loved the condo first time around and it was even better for this stay with improvements to the condo and all building works...
    5 of 5 bubbles Reviewed 26 October 2014
    Lovely, clean and well furnished condo with great view onto the Gulf. Condo was large with ample room for all six of us with screened verandah ideal for relaxing and watching...
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    1 / 36
    5 of 5 bubbles (1) Excellent
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Patio
    • Internet Access
    • Grill
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of Banana's Foster Guest House This spacious 2 bedroom apartment takes up the first floor of this historic Key West home located on the corner of Caroline St and Simonton Dt. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4 of 5 bubbles (2) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Hot Tub
    • Terrace
    • Balcony
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed 10 October 2016
    The location is nice because it's quiet. The unit and kitchen supplies need updating. The view from the balcony is nice. The pool area is nice.
    5 of 5 bubbles Reviewed 15 March 2016
    This 2 bedroom condo in Key West was really great. The staff went out of their way to make us feel welcome. They checked to see if our room was ready and clean early and it was...
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    1 / 28
    4.5 of 5 bubbles (42) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Balcony
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-styled complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 17 November 2016
    Not even a block off Duval near the Southernmost end of the island (i.e., the quiet end of Duval), this efficiency was a great find. Located in a renovated old house with...
    3 of 5 bubbles Reviewed 10 November 2016
    The location is great. Right next to duval street. But it's definitely too small even for 4 persons.... we were walking in each other. One fan wasn't working and in the kitchen...
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    1 / 23
    5 of 5 bubbles (1) Excellent
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Waterfront
    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Canal-front house, quiet and in the nicest of neighborhoods (Plantation Key Colony). Situated on the bayside on Mile Marker 90. All remodeled,white tiled floor, furnished in wicker/rattan and decorated with the ocean & beach ambiance in mind. Boat dockage in the back and easy access to few boat... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    1 / 35
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Air Conditioning
    • Satellite TV
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    • Hot Tub
    • Balcony
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM to 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    4 of 5 bubbles (7) Very good
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Patio
    • Balcony
    • Internet Access
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    • DVD Player
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    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Listen to the tropical songbirds at sunrise. Walk to John Pennekamp Park. Get away from the hustle and bustle of South Florida. This property is nicely landscaped with palms and flowers and has a water view. There is a neighborhood park 100 meters away with water access for kayaking , swimming,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    4 of 5 bubbles Reviewed 20 June 2016
    This is the first time we have rented a house when traveling. It was a fantastic decision, and this house was almost perfect for our big family. There are 2 bedrooms with...
    4 of 5 bubbles Reviewed 29 May 2016
    We were herev with family. 4 People with enough room to sleep for everybody. The House is clean and after a small talk with the owner, he didnt know the washmaschine wouldnt work...
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    1 / 28
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Private Outdoor...
    • Balcony
    • Satellite TV
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    A Key Escape 3 br 2.5 bath w/ private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Hot Tub
    • Shared Outdoor Pool...
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    • Internet Access
    • Terrace
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 33
    4.5 of 5 bubbles (24) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sea Breeze features all the amenities of then some! A full kitchen with glass top stove, dishwasher, icemaker, blender, toaster, coffee maker and radio/CD player to play your favorite Jimmy Buffet CD while enjoying a fresh cup of isn't a better way to start your day in paradise! A covered... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 7 February 2015
    For $1700 for 5 nights, I expected a little more. First, I considered doing laundry on the last day, but the dryer door doesn't close (as evidenced by the tape marks all over it...
    5 of 5 bubbles Reviewed 12 December 2014
    The condo was great. The place was clean, comfortable, and 1/2 block from Duval Street. We were able to walk everywhere we needed to go. There was a porch off of one of the...
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    1 / 23
    4.5 of 5 bubbles (21) Very good
    Key West
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    AUDUBON'S LIVING ROOM HAS JUST BEEN REFURBISHED WITH NEW FURNITURE INCLUDING NEW CHAIRS AND A NEW QUEEN SLEEPER SOFA! The Audubon House is an historic free-standing one bedroom cottage featuring all the comforts of home, and more! The spacious, beautifully furnished great room features a living... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 8 December 2014
    The home was clean, centrally located. Also, safe. will be coming back and using you guys again on our next trip to key west!
    4 of 5 bubbles Reviewed 20 November 2014
    We booked here for one night because of the location. This worked out well for 2 couples - one private bedroom with full bath and separate entrance, one pull-out sofa bed with a...
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    1 / 27
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
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    • Terrace
    • Balcony
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Grill
    • Terrace
    • Air Conditioning
    • Satellite TV
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 36
    4.5 of 5 bubbles (2) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Part of TROPICAL VILLAGE Tropical Village Retreat - Lush gardens surround this lovingly restored two-story vacation house. This upstairs suite has two bedrooms each featuring a queen bed. The fully equipped kitchen is perfect for the serious cook or enjoy your meals on the gas BBQ grill in a... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 22 August 2016
    Love the place! Location was good. There was an issue with ants in the kitchen. Also, I was issued 3 keys and 1 of the keys was not for our place. Changed the key with...
    5 of 5 bubbles Reviewed 21 April 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information. I did not stay in this particular cottage but our guests had rave...
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    1 / 32
    4.5 of 5 bubbles (29) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of the Nightly Group PALM GARDENS Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 17 February 2015
    My wife and I recently rented this unit for the first week of February. Overall, I’d call it a solid good! We liked the location, with a grocery store and an excellent selection...
    5 of 5 bubbles Reviewed 2 September 2014
    I stayed here this past Labor Day weekend for a friend's bachelorette party. There were 10 of us, and the Heron Hideaway as well as the three other one-bedroom condos in the area...
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    1 / 28
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
    • Satellite TV
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-style complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a... View all property information
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    Key West, Florida Keys 33040
    1 / 37
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Grill
    • Satellite TV
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    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (8) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    One half of the group unit Tradewinds and Opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design. The Webster Dictionary dates windward back to 1549; defined as, the side or... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 10 July 2016
    Our only wish is for additional air conditioning units in living area and bathroom. Everything else was wonderful
    4 of 5 bubbles Reviewed 21 July 2014
    Very nice place, beds were super comfy. Close to Duval but quiet. This place does have a parking spot, but we were not told about it until I called.
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    1 / 6
    5 of 5 bubbles (4) Excellent
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Housekeeping...
    • Shared Outdoor Pool...
    • Waterfront
    • DVD Player
    • Ocean Views
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    About this property
    Escape to Key Largo's ultimate weekend or vacation getaway ~ the best Inn in the Florida Keys. Located directly on the Atlantic Ocean, in unspoiled Largo Sound. Offering the best access to the finest of Florida Keys charter fishing, Everglades's excursions, Eco-tours, snorkeling and scuba diving.... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 bubbles Reviewed 5 June 2015
    one of the nicest place&staff i have ever rented hope to go back soon and visit gilda & crew DANNY&SHIRLEY TRY IT YOU WILL LIKE IT DANNY
    4 of 5 bubbles Reviewed 7 March 2015
    We truly enjoyed our stay at the Flats. Tucked away off the beaten track, it was a nice quiet spot with a beautiful waterfront (not an ideal spot for swimming but great for...
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    1 / 24
    4.5 of 5 bubbles (31) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The Monroe Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 16 January 2015
    This rental company is one of the best - I've had numerous occasion to use their services. We arrived very early, but were allowed to park our car at the rental location and walk...
    5 of 5 bubbles Reviewed 17 November 2014
    We had a great stay and will for sure be staying in one of these cottages again. Great location close to nice restaurants approx midway Duval and North 2 blocks. Stayed for a long...
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    1 / 27
    4 of 5 bubbles (25) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
    • Shared Outdoor Pool...
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 9 September 2015
    I just returned from a long weekend in beautiful Key West and the Verde Suite was a perfect choice. It was clean, comfortable and just far enough away from the hustle of the town...
    4 of 5 bubbles Reviewed 30 June 2015
    We really enjoyed our few days here and thank goodness for the refreshing pool because it was HOT HOT HOT! We enjoyed meeting a couple of other folks in the quaint cluster of...
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    1 / 28
    3 of 5 bubbles (2) Average
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Balcony
    • Satellite TV
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    • Air Conditioning
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    *** 1 Private, covered parking spot is included when you rent this particular vacation condo Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 10 March 2015
    We found the unit was as advertised, and clean, quiet, and comfortable. Most things worked well, though one of the locks on the door didn't work, and the lock on the patio door...
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    1 / 28
    4.5 of 5 bubbles (2) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
    • Grill
    • Terrace
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    • Patio
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Brand New to the Rental Market! Part of Banana's Foster Guest House This cozy 2nd floor studio is perfect for a couple looking to be in the middle of the Duval action! After entering the compound from the shared off street parking into the courtyard with shared plunge pool and BBQ grill, go... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 30 March 2016
    Loved the stay here. Close to Duvall. Could walk to anywhere on the island including historical sites, any restaurant. Centrally located. Rooms very clean and spacious. Only...
    5 of 5 bubbles Reviewed 11 November 2014
    This place was perfect for what we were looking for: Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom, one...
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    1 / 30
    4.5 of 5 bubbles (3) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Part of Southern Palms ROYAL PALM (formerly Little Palm) - What an idyllic setting! Picture the most perfect romantic getaway cottage with all the must have's for a great Key West vacation - in a setting that nature provided in the late 1800's - the hardwood canopy is stunning! The Tommy Bahama... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed 16 May 2016
    As far as the accommodation is concerned, the location is unsurpassed. The cottage is clean, comfortable and well appointed. Sadly what let's the place down are the agents/support...
    5 of 5 bubbles Reviewed 11 November 2015
    This is the second time we've stayed in this rental complex. The first time upstairs and now this time in the back. The location off of Whitehead is perfect for everything we love...
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    1 / 28
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • Air Conditioning
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located just steps from Duval St - right off the corner of Amelia and Duval - "Duval Quarters" is the perfect combination of location, luxury and roominess! This 1 bed 1 bath condo is a part of the historic Casa De Luces condominium complex and is now managed by Key West Vacation Rentals, which... View all property information
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    Key West, Florida Keys 33040
    1 / 39
    4.5 of 5 bubbles (9) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
    About this property
    Amelia House is surrounded by fine restaurants, art galleries, and fine shopping. The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which... View all property information
    Location Information
    Key West, Florida Keys
    4 of 5 bubbles Reviewed 13 January 2015
    Great location! 1/2 a block off the main street (Duval) and convenient to everything, but in a quiet dead end street. Private parking! (Hard to park anywhere in the Keys...
    5 of 5 bubbles Reviewed 12 January 2015
    Its just a few steps away from where all the actions is. Considering the location, it is actually quiet at night. We got ourselves lock out while drinking and partying at the...
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    1 / 26
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Parking
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    • Internet Access
    • Balcony
    • Terrace
    • Air Conditioning
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9am - 6pm daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 28
    2 of 5 bubbles (1) Poor
    Key West
    4 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Terrace
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    • Hot Tub
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    ***There will be maintenance scheduled in the apartment underneath this rental starting in November 2016 and lasting throughout approximately through March 2017. Moderate noise can be expected Seaport Suite is available for daily vacation rentals and located on the second floor of an historic Key... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    4 of 5 bubbles (24) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Internet Access
    • DVD Player
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Southernmost Retreat features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. The perfect place to listen to your favorite music while... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 22 January 2015
    We just spent a week at SMR and really enjoyed our stay! Close to duval without the noise! We could hear some live music from la te da one night, but it was nice to sit on the...
    4 of 5 bubbles Reviewed 23 November 2014
    Location right on Duval was awesome! We were close to everything! The condo has a great layout. Fully functional kitchen. 2 bedrooms with TVs. Outdoor space with hot tub which...
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    1 / 20
    5 of 5 bubbles (1) Excellent
    Summerland Key
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • Patio
    • Washer
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    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Amazing canal front 3 bed 2 bath open concept house located in prestigious community of Summerland Key Cove. It is the first canal from open water and one of just a few flow-through canals providing excellent water quality. The canal is deep and wide. Expect to see lobsters, crabs and other sea... View all property information
    Location Information
    Summerland Key, Lower Keys 33042
    5 of 5 bubbles Reviewed 26 March 2016
    Whatever I'd hoped for, this vacation home has without question, surpassed any and all expectations! Excellent location; in a quiet and beautiful strip. Loved relaxing on the...
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    1 / 28
    4.5 of 5 bubbles (23) Very good
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 7 April 2015
    Very well decorated an equipped with everything needed. Nice open area, the pictures do not do it justice. Larger living area and dining than the photos show. Two nice balconies...
    5 of 5 bubbles Reviewed 6 August 2014
    Excellently furnished, Immaculately clean. Completely up to date appliances and amenities. (Washer & dryer just off the kitchen!) Tip-Bring your own laundry detergent Traveled...
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    1 / 36
    5 of 5 bubbles (13) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This house is in a quiet residential neighborhood where loud boisterous parties are not appropriate. This 2 bedroom, 2 bath, 2 story house has an open floor plan featuring lots of pine walls and floors throughout. Upstairs is the king bedroom and a full bath and downstairs is the second bedroom... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 9 November 2014
    We were very happy with this house rental. The pictures only hold a small window into this gem. Walking distance to Duval (although a cab was only $6 if needed). Great living...
    3 of 5 bubbles Reviewed 12 August 2014
    Pros - charming cottage, two bathrooms, private pool, dish washer, washer and dryer, nice bed and linens, just a few blocks from Duval, plenty of street parking. Cons - across...
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    1 / 22
    4 of 5 bubbles (37) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Patio
    • Grill
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    One half of the group unit Tradewinds Opposite Windward Isle , the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and... View all property information
    Location Information
    Key West, Florida Keys 33040
    3 of 5 bubbles Reviewed 15 December 2015
    We stayed in this property for two days. We had a good time. Staff is friendly. They have everything what we need there. I read reviews about this property and some one mentioned...
    4 of 5 bubbles Reviewed 11 December 2015
    Nice location. Hot tub, patio nice, porch fun to watch traffic a passerbys with morning coffee. Houe is cute but needs a little TLC. Fingerprints on walls and doors, missing...
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    1 / 29
    4.5 of 5 bubbles (27) Very good
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed 16 September 2015
    Very nice place in a great location. Close to everything and very convenient. Staff was excellent, place was clean and service by the concierge was top notch. I would stay...
    4 of 5 bubbles Reviewed 2 September 2015
    All and all, I would return to this location because of the LOCATION. The unit itself served its purposes, but there were some issues. The formica in the kitchen was all cracked...
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