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Holiday Rentals with Pools in Florida Keys

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    $4,906
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    1 / 15
    4.5 of 5 stars (2) Very good
    Key West
    House Rental - 
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    1 / 30
    5 of 5 stars (10) Excellent
    Key West
    Apartment - 
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    $387
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    1 / 12
    4 of 5 stars (14) Very good
    Key West
    Apartment - 
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    1 / 17
    5 of 5 stars (2) Excellent
    Key West
    House Rental - 
    2 Bedrooms / 3 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Hot Tub
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    • x
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    About this property
    30 DAY MINIMUM RENTAL OLIVIA COTTAGE Recently featured in Coastal Living's 'Guestbook' column, this charming Old Town house has recently been completely and tastefully renovated by its owners. Located just across the street from Key West's historic city cemetery, truly a tourist attraction in our... View all property information
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    5 of 5 stars Reviewed 9 August 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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    $226
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    1 / 17
    4 of 5 stars (7) Very good
    Marathon
    Apartment - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    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
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    5 of 5 stars Reviewed 27 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...
    5 of 5 stars Reviewed 19 July 2014
    Really enjoyed our stay. Two adults and four teenagers. We had more than enough space. Also grocery stores close by and only an hour drive from the keys. Also a great snorkel...
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    1 / 27
    Key West
    House Rental - 
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Gym
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    • x
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    About this property
    Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home in the 500 block of Olivia Street. The updated kitchen features granite counter tops and beautiful wooden floors. Your bathroom offers a large walk-in tiled shower. A semi-private pool with... View all property information
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    1 / 19
    4.5 of 5 stars (37) Very good
    Key West
    Apartment - 
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (37) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • ?
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
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    4 of 5 stars Reviewed 8 July 2014
    1960s property but well maintained with a good pool, new gas grills (all the better for cooking your catch) and located right on the marina. Our unit (1040) was on the first floor...
    4 of 5 stars Reviewed 10 September 2013
    had a great time, I'll be back.
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    $3,010
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    1 / 19
    4.5 of 5 stars (5) Very good
    Duck Key
    House Rental - 
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (5) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    Private residence on Duck Key. 2 bedrooms and 2 baths upstairs with a seperate one bedroom one bath apartment downstairs. Apartment has own kitchen and family room. Private dock with heated pool. Ocean kayak and fishing rods included. Catch tarpon right off the dock. House extensively... View all property information
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    5 of 5 stars Reviewed 10 October 2014
    Stayed at Key Breeze with some old friends for a week of fishing. As the one that booked it, I came away a hero. The house was just perfect for our needs. Clean and up to date...
    3 of 5 stars Reviewed 5 February 2014
    We didn't realize the strength of the current behind this house when we booked it. Swimming is next to impossible and the fishing wasn't that great. We ended up renting boats for...
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    1 / 20
    Key Largo
    House Rental - 
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Pets allowed
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    • Suitable for children
    • x
    • ?
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    About this property
    MINIMUM RENTAL 1 MONTH: Villa Bella is a fabulous 3 BR/3 BA two-story townhouse. This end unit townhome 'lives' on the 2nd floor. The kitchen, dining and living areas are all open to each other in a great room with a gorgeous vaulted ceiling. There are 2 bedrooms and 2 baths on this upper level... View all property information
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    1 / 42
    5 of 5 stars (4) Excellent
    Key Largo
    House Rental - 
    6 Bedrooms / 7 Bathrooms / Sleeps 14
    Overview Reviews (4) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
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    • Hot Tub
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    • Private Fishing...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    About this property
    This is a monthly rental, please contact for rates, as they vary depending on how many people and how many days are occupied during the month.... Minutes from the mainland and an hour from Miami Airport...This giant estate with 2 separate residences come with contemporary mediterrean style... View all property information
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    5 of 5 stars Reviewed 4 August 2014
    What can I say that would do this place justice? Privacy with a gated entrance on famed Millionaire's Row in Key Largo. Or Maybe the spectacular views from all over the...
    5 of 5 stars Reviewed 31 December 2013
    This luxurious double house is ideal for a large family group. The location is convenient, the houses are spacious and well equipped, the pool and spa are very comfortable, and...
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    1 / 22
    5 of 5 stars (6) Excellent
    Cudjoe Key
    House Rental - 
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (6) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
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    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    2 Bedroom+/2 Bath+ Tropical Paradise Home with floating dock, small beach, heated dipping pool and hot tub. This has been a popular honeymoon and anniversary celebration home for over 10 years. Very romantic. You wake up to the sunrise reflecting on the water and don't even have to get out of... View all property information
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    5 of 5 stars Reviewed 15 January 2015
    A lovely waterfront home facing south on Cudjoe Bay. Outside you have palms, a dock, hot tub, pool, hammock, bikes, kayaks, adirondack chairs, deck, umbrella table, flowers...
    5 of 5 stars Reviewed 11 January 2015
    In October I contacted owner of this property and I was glad it's was available! We were absolute in love with place from the moment we saw it! It has everything you've ever need...
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    $4,390
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    5 of 5 stars (6) Excellent
    Cudjoe Key
    House Rental - 
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (6) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Designed as the ultimate vacation rental. Five Bedroom/Three Bath Oceanview Home with Heated Pool and Hot Tub. Panoramic Ocean Views. Sleeps 10+. Located on Cudjoe Key. Includes private boat dock, private beach, kayaks, and bikes. Weber BBQ grill, Lot's of lounge chairs and two hammocks.... View all property information
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    5 of 5 stars Reviewed 29 July 2014
    We rented this home for a week in July for a quiet family getaway. This was my first time renting a home in the keys, I have done so many times in the Smokey Mountains but never...
    5 of 5 stars Reviewed 4 March 2014
    We had a great experience at Fandango! The house looks exactly like online photos. The kitchen is well equipped, house is very clean, lots of bath and beach towels and a good...
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    $1,452
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    1 / 99
    5 of 5 stars (72) Excellent
    Key Colony Beach
    House Rental - 
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (72) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Hot Tub
    • Housekeeping...
    • Internet Access
    • Ocean Views
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • x
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    About this property
    'KEYS OCEAN DRIVE' is #1 with MOST 5 Star Guest Reviews (67) in the ENTIRE FL Keys! Plus we are #1 with the MOST Guest Reviews (72) in the FL Keys! Plus 99+ Photos on our Island of KCB ('click' photos /don't forget to read descriptions)! ONLY 2 WEEKS LEFT as short term rentals: #1. c/i 4/11... View all property information
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    5 of 5 stars Reviewed 9 March 2015
    We just enjoyed our second visit to Key Colony Beach. We stayed at Keys Ocean Drive both times (the month of February 2015 and 2014). This home is immaculately maintained and...
    5 of 5 stars Reviewed 30 January 2015
    We were first time visitors to Key Colony and can't wait to go back. We stayed at this property over Christmas 2014 and the home is as beautiful as the pictures. Key Colony is a...
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    4.5 of 5 stars (2) Very good
    Key Largo
    House Rental - 
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    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
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    4 of 5 stars Reviewed 8 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...
    5 of 5 stars Reviewed 24 July 2014
    Our unit was just big enough for the two of us having one bedroom, one bath. Walk out about 15 ft. to the pool and another 20 ft to the water. Beautiful sunsets! Diving nearby...
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    1 / 13
    3.5 of 5 stars (3) Average
    Key West
    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • ?
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    About this property
    30 DAY MINIMUM RENTAL Walk the historic streets of Key West, live in Old Town in a quiet residential neighborhood. Just two blocks from Duval Street, it is a quick walk or bike ride to all of Key West's attractions, including it's close proximity to the Historic Seaport area. This is an lovingly... View all property information
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    5 of 5 stars Reviewed 19 June 2009
    We had an absolutely delightful time! We have been renting homes in the Keys for years and found this to be our best experience yet. The folks at Rent Key West were so helpful...
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    5 of 5 stars (3) Excellent
    Islamorada
    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Fishing...
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • x
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    About this property
    Thank you for considering Our home in the Florida Keys!... Our slice of Paradise! Stay at a Luxury Townhome at Executive Bay Club (Islamorada , Florida ) The Executive Bay Club is located in Islamorada which is best known for it's crystal blue water where you can enjoy sport fishing, snorkeling,... View all property information
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    1 / 8
    5 of 5 stars (1) Excellent
    Key West
    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Pool Table
    • Private Outdoor...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Note, this is a monthly rental. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features which... View all property information
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    5 of 5 stars Reviewed 9 December 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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    5 of 5 stars (1) Excellent
    Key Largo
    House Rental - 
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
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    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
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    About this property
    This Oceanfront home is totally re-modeled with all top of the line finishes and ready to enjoy your Keys Vacation. Oceanfront Pool Home. 3 Story 5 Bed/5.5 Bath 4300+ sq. ft. of luxury and fun. Protected deepwater Dockage & Panoramic Ocean Views. This great executive rental features Ocean Views... View all property information
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    5 of 5 stars Reviewed 12 January 2015
    Thank you for allowing us to stay in your amazing property! The pictures really do not do it justice, surely one of the finest houses in Key Largo Absolutely first class and...
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    5 of 5 stars (1) Excellent
    Cudjoe Key
    House Rental - 
    4 Bedrooms / 3 Bathrooms / Sleeps 12
    Overview Reviews (1) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Beautiful four thousand plus square foot home located on Cudjoe Key. Private beach and 30 foot swimming pool with 10 foot waterfall hot tub. Huge master suite overlooking the ocean. The house comes with BBQ grill and single and double kayaks. Spectacular views can be enjoyed from the screened... View all property information
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    5 of 5 stars Reviewed 6 January 2014
    We are 3 families, 5 adults and 3 teenagers. The 4 bedrooms are each very private and quiet. There are 2 master bedrooms each with ensuite bathrooms; 1 upstairs and 1 downstairs...
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    4 of 5 stars (23) Very good
    Key West
    Apartment - 
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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 opens to the living room,... View all property information
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    3 of 5 stars Reviewed 14 March 2015
    We have stayed in quite a few places in Key West, and the location was good, but there are things to be aware of. One thing to know is that it is a vacation rental unit in a...
    1 of 5 stars Reviewed 11 March 2015
    This condo was perfectly situated just off Duval, the management company was professional, and the place was clean and comfortable. However, I will never stay here again. At 3 am...
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    1 / 25
    5 of 5 stars (2) Excellent
    Key West
    House Rental - 
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This home has a unique pricing structure. While it can rent for less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial (25% off) Monthly Rental discounts. Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full... View all property information
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    5 of 5 stars Reviewed 8 June 2011
    This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is first...
    5 of 5 stars Reviewed 6 March 2010
    The heated pool and lush backyard foliage were the draw to this well appointed home. Parking was a nightmare, the neighbor to the right facing the house was most unpleasant. A...
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    4 of 5 stars (1) Very good
    Islamorada
    Apartment - 
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • ?
    About this property
    Beautiful bayside condo, 3bedrooms 2baths, sleeps 6 comfortably, new sealy beds in all rooms with cable and wifi. Newly furnished and clean. Comes with 36 foot boat slip in the marina. There is a boat ramp on the property along with a brand new pool. Deep water dockage and deep channel to... View all property information
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    4 of 5 stars Reviewed 16 June 2014
    We spent a full week at this Futura Yacht Club rental, which we enjoyed very much. Here are the pro's and con's: Pro: Boat slip accommodated our 29 foot boat well Fresh water...
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    5 of 5 stars (6) Excellent
    Grassy Key
    House Rental - 
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
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    About this property
    La Casa Habana is a 3 bedroom , 2 bath house overlooking the Gulf of Mexico on exclusive and private Morton St. on Grassy Key. This house has been extremely popular for over 10 years. It has everything you need for a great vacation-bikes, kayaks, snorkel gear, fishing gear, Cable TV and wifi... View all property information
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    5 of 5 stars Reviewed 26 June 2014
    My husband and I and our three grown children (boys ages 18, 20 and 23) thoroughly enjoyed our stay at La Casa Habana. The home was even nicer than in the photos. The kitchen and...
    5 of 5 stars Reviewed 14 June 2014
    We LOVE La Casa Habana! They have really made this feel like your in your own home. Has everything you could possibly need for your stay...just pack your clothes and pick up...
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    $142
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    4 of 5 stars (5) Very good
    Marathon
    Apartment - 
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Located in the centre of Marathon. This destination is perfect for discovering the beautiful Florida Keys. One hour's drive from Key West or Key Largo. Marathon is famous for the sportfishing including but not limited to Marlin, Sailfish, Mahi-Mahi and there are numerous places to rent a boat,... View all property information
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    4 of 5 stars Reviewed 10 November 2014
    Really liked the location and balcony on the front & back. The TV's were nice. The bed was very comfortable. The kitchen was suitable. It may need new carpeting soon. Over all...
    5 of 5 stars Reviewed 29 October 2014
    We stayed in this one bedroom unit, in a complex of about 6 buildings, overlooking a canal off the ocean side of marathon key, fl. We used the key west transit bus to travel to...
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    Key West
    House Rental - 
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    30 DAY MINIMUM RENTAL Welcome to the Mango Menagerie - a treasury of island colors combined with Key West charm. Located in the heart of Old Town, this home is located just one block from the ever popular Cuban restaurant El Siboney and one block from the local's favorite Flaming Buoy restaurant.... View all property information
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    5 of 5 stars (1) Excellent
    Marathon
    House Rental - 
    3 Bedrooms / 1 Bathroom / Sleeps 8
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Escape To The Florida Keys....Spend a Week in The Islands~ Seaside! Seaside Escape is the ultimate in a family vacation.....easy, and quick access to the Atlantic for a day of fishing, snorkeling or just plain enjoying boating out on the ocean for the day. For those of you that consider... View all property information
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    5 of 5 stars Reviewed 28 February 2015
    We absolutely loved this house! Everything was perfect 😃 The pool was wonderful and the scenery was beautiful! The house was great as well. Everything that we needed was...
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    5 of 5 stars (1) Excellent
    Islamorada
    Apartment - 
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of... View all property information
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    5 of 5 stars Reviewed 17 November 2014
    my husband and 2 friends stayed in this unit for 4 days and 3 nights. they found the condo to be clean, plenty of space and conveniently located. they would definitely stay...
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    5 of 5 stars (1) Excellent
    Cudjoe Key
    House Rental - 
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Hot Tub
    • Internet Access
    • Private Fishing...
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Dock you boat or jet skis behind this nicely decorated 2 bedroom 2 bathroom(sleeps up to six people) on a deep water canal just a stone's throw from the open water of the Atlantic Ocean. On-site amenities include an 80 foot heated swimming pool, seperate pool for the kiddies, jacuzzi, marina, boat... View all property information
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    5 of 5 stars Reviewed 26 October 2014
    Awesome Cudjoe Key get a way. Good sized personal dock behind the house for my boat and great Atlantic Ocean access, was in deep water in about 10-15 minutes. Good fishing off the...
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    5 of 5 stars (3) Excellent
    Marathon
    Villa - 
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Luxurious direct bayfront townhome with dock, upgraded unit. Jan, March and April 2015 are now available. $6,500/month. best location in the 50's overlooking large green yard and open bay with slip in front. 3 bedroom, 2.5 bath. Built in 2006. gated waterfront community. Dock for 32 ft boat,... View all property information
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    5 of 5 stars Reviewed 4 July 2014
    This was my second rental through Keys Caribbean . Excellent Price, excellent service, excellent location . A hidden jewel in Marathon.
    5 of 5 stars Reviewed 21 June 2014
    Best condo we have ever rented Very spacious, well maintained, nicely decorated. Beautiful view, excellent boat dockage. Only complaint: no HD cable for World Cup
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    $8,973
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    1 / 21
    Key West
    House Rental - 
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    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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    5 of 5 stars (5) Excellent
    Marathon
    Apartment - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    When you arrive, you know you've come somewhere very special. This condo has the most spectacular views of the the Atlantic Ocean and a pristine heated pool. Located on Coco Plum Beach in Marathon, Florida Keys, you're in a secluded yet central base for all Keys sightseeing and activities, if you... View all property information
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    5 of 5 stars Reviewed 21 December 2013
    This is the ideal place for a relaxing break, perfectly situated in the middle of the Florida Keys, so you have the facilities of Marathon on your doorstep and can easily drive to...
    5 of 5 stars Reviewed 7 October 2013
    This condo has an amazing view of the ocean! When we weren't walking on the beach or swimming in the pool it was nice to sit on the patio and just enjoy our surroundings. The...
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    5 of 5 stars (3) Excellent
    Long Key
    Apartment - 
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Ocean Views
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Fishermans Paradise at Oceanside Isle Condominiums with 1,800 Square Feet of Living Space, on Long Key, which is a Secluded Island with direct access to both Atlantic Ocean and the Bay of Florida through Channel #5. Expansive Master Suite and with Large Tub & walk-in shower. Relax on your one of... View all property information
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    5 of 5 stars Reviewed 10 December 2014
    my family stayed here the week of december the 5 2014 from the first contact with bob till the day we left can say nothing but great things bob got right back with me asap he made...
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    5 of 5 stars (2) Excellent
    Islamorada
    Townhouse - 
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Ocean Views
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    BEAUTIFUL NEWLY REMODELED 3 BEDROOM, 2 FULL BATHROOM VACATION RENTAL IS LOCATED IN THE EXECUTIVE BAY CLUB. BREATHTAKING BAY VIEW FROM YOUR OWN BACK YARD! UNIT HAS BRAND NEW CUTOME KITCHEN CABINETS WITH GRANITE COUNTER TOPS. ALL STAINLESS STEEL APPLIANCES, DOUBLE DOOR REFRIGERATOR, DISHWASHER,... View all property information
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    5 of 5 stars Reviewed 24 February 2015
    The place was beautifully decorated and in excellent condition. From the patio you had an excellent ocean view that was a short walk to a small beach. My teens has a blast and...
    5 of 5 stars Reviewed 24 February 2015
    When we first contacted the owner regarding the rental, she responded immediately and was very nice and helpful. The unit was impeccable when we arrived and the location in the...
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    5 of 5 stars (1) Excellent
    Islamorada
    Apartment - 
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Gym
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    This remodeled 2 bedroom 2 bath condo is directly on the Atlantic Ocean with ground access via a spiral staircase. Stunning views from the Master bedroom and balcony. Wake up to the sunrise and enjoy your leisurely day on the boat, at the nearby sand bar, or lounge in the zero entry pool. There... View all property information
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    5 of 5 stars Reviewed 7 January 2012
    My husband and I stayed here for almost 2 weeks for our honeymoon/vacation over the Christmas holiday. We were nervous about renting something over the internet that we had never...
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    Key West
    B and B - 
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Housekeeping...
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Eyebrow House is a very spacious one-bedroom suite with a large front porch and palm tree-filled private fenced-in yard overlooking a quiet side street. Our guests enjoy the best of both worlds as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a half block away.... View all property information
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    $775
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    1 / 29
    5 of 5 stars (18) Excellent
    Marathon
    Villa - 
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (18) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Located in the secluded Indigo Reef Resort in Marathon, this luxury vacation rental is pure paradise. You will immerse yourself in long leisurely days of boating, lounging by the pool and watching spectacular sunsets from your back porch. Located just 90 miles south of Miami and 45 miles from Key... View all property information
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    5 of 5 stars Reviewed 19 March 2015
    LOVE,LOVE,LOVE this place and all it has to offer!!! The only thing I would recommend is that the NO Trailers on the property rule should be made clear. Hauling a tailor from PA...
    5 of 5 stars Reviewed 29 October 2014
    Indigo Reef. Secluded, serene, tropical. Wake up every morning and have coffee on the back porch overlooking a gorgeous canal lined with palm trees. Walk a few steps to a huge...
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    $994
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    5 of 5 stars (1) Excellent
    Key Largo
    House Rental - 
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    MINI VACATIONS 3 DAYS 2 NIGHTS $199.00 April 1 - May 15, 2015 This Key Largo property is a paradise in a gated private community. This comfortable park model trailer includes cable TV, full kitchen, bathroom, Queen size bed in master bedroom and much more. Outside terrace with BBQ grill and... View all property information
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    5 of 5 stars Reviewed 12 March 2015
    Oscar was a great person and a very trustworthy person to deal with from the beginning of the registration to the day we sadly departed. We found our unit clean, comfortable and...
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    $185
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    5 of 5 stars (4) Excellent
    Key Colony Beach
    House Rental - 
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Key Colony Beach house description SPECIAL rate of $999.00 for 4 guests (may have 6, $35 per extra person, 6 max total) Valid for Spring and Fall (except Thanksgiving), Summer is $1100 per week, Please check calendar for open weeks. Weekly rental, Saturday-Saturday, excluding Thanksgiving NEW... View all property information
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    5 of 5 stars Reviewed 3 November 2014
    We had an awesome time at "Key Escapes", even though the weather did not really cooperate much of the time. The location of this duplex was wonderful, right on the channel with...
    5 of 5 stars Reviewed 30 June 2014
    From the beginning to the end, it was the best vacation ever! The owner was such a delight to work with! KEYS ESCAPE rental was perfect! If you looking for a real keys...
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    4.5 of 5 stars (8) Very good
    Key Largo
    Apartment - 
    2 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Ping Pong Table
    • Private Fishing...
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    A view of the pool off your patio and the Florida Bay sunset glows at your front door. Tropical breezes and gardens grace the gated condo community. Yes, laptops do work in the apartment! At Moon Bay condominium you will have the opportunity to relax in the heated pool, exercise in the tennis... View all property information
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    5 of 5 stars Reviewed 10 August 2014
    had a great time in key largo, the condo was great, had everything you need as a home from home, good sized rooms ,great working air con, all mod cons you need, very clean, plenty...
    5 of 5 stars Reviewed 15 April 2013
    We have had a wonderful holiday in Moon Bay. Condo was larger than we were expecting. Both bedrooms large and clean. Lovely patio to sit out on. The complex itself had...
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    Key West
    Apartment - 
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Enjoy this quiet 2 bedroom, 2 bath condominium tucked away from all the excitement of Key West. Spend your days lounging by the shared lagoon shaped pool surrounded by beautifully lush tropical foliage. Or take just a short walk to Smather’s Beach where you can spend your time snorkeling,... View all property information
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    4.5 of 5 stars (2) Very good
    Key Largo
    Apartment - 
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Private Fishing...
    • Safe
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    The condo is located in a complex called Moon Bay More like a resort than a condominium. Free tennis courts, saunas, a private boat slip, and a dock for fishing and saltwater swimming, to mention just a few of the amenities. The unit is on the fourth floor of an elevator building, making for... View all property information
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    5 of 5 stars Reviewed 10 January 2015
    We stayed in A407. This condo unit is nicely set up with everything you could need. The beds are very comfortable with the master bedroom having a view of the bay, so nice to...
    4 of 5 stars Reviewed 8 October 2013
    We stayed in condo B-106, owned by Gloria, who prepared everything for our arrival. Erin, her housekeeper met us on arrival and showed us round. Everything was as promised. The...
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    5 of 5 stars (4) Excellent
    Key West
    Cottage - 
    Studio / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    The kitchen offers an under-counter fridge, microwave, coffee maker, toaster, blender and everything to cook, prepare and enjoy a light meal…and don’t forget the BBQ grill and Ice-maker by the pool! This very comfortable unit also has a very sexy two-person custom shower with glass door,... View all property information
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    5 of 5 stars Reviewed 1 July 2014
    The unit was clean and in a great location. Maintenance was attentive and cleaning staff also. The only trouble we had was virtually ever night some giant vehicle was running...
    5 of 5 stars Reviewed 4 April 2014
    The place we stayed at was small inside, but big on the outside space. The courtyard was beautiful and added another dimension to the space. Like a living room in the tropics!
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    $129
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    1 / 27
    5 of 5 stars (1) Excellent
    Key West
    Apartment - 
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights*** MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO EXCEPTIONS Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light and bright... View all property information
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    5 of 5 stars Reviewed 18 March 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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    4.5 of 5 stars (24) Very good
    Key West
    Apartment - 
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
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    5 of 5 stars Reviewed 15 January 2015
    My husband and I stayed here with another couple and it was great! Great location, lots of room! There is definitely a master suite and a second bedroom but both rooms have...
    5 of 5 stars Reviewed 13 January 2015
    Townhouse was nice,clean,stocked well and as promised .the location was great...walking distance to everything we wanted..quiet..pool was well kept, rental company was accessible...
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    $198
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    Marathon
    Apartment - 
    2 Bedrooms / 1 Bathroom / Sleeps 4
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The Cats Eye has a queen bed in the bedroom and a sleeper sofa in the living/dining room. Cable color TV, A/C, paddle fans and full kitchen. BBQ grill. Light and bright. Recommended for 2 but will accommodate 4 people including children. View all property information
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    $269
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    1 / 26
    5 of 5 stars (1) Excellent
    Key West
    Apartment - 
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many... View all property information
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    5 of 5 stars Reviewed 6 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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    $97
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    4.5 of 5 stars (7) Very good
    Key Largo
    House Rental - 
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Pelican Harbour: Wide Open Ocean Views, with Cozy Trailer on Property... a 2005 Frontier, 25 FT. One Bedroom, One Bath..... PELICAN HARBOUR is a Great Property you are literally on the Water, step out and Wide Open Views, Exterior Stereo, Chaise Lounges, Seating Area and BBQ Outside. Fish from... View all property information
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    4 of 5 stars Reviewed 25 March 2015
    We were assisted by Mr. Laredo from the beginning of the rental process every step of the way. The property was in good repair and appeared clean. Within the unit we found ample...
    4 of 5 stars Reviewed 4 January 2015
    Nestor was a great host! The camper was exceptionally clean, beautiful setting but a bit away from town activities. If you want a great place to relax and enjoy the sunshine this...
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    $5,810
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    1 / 43
    4 of 5 stars (1) Very good
    Key West
    House Rental - 
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    28 NIGHT MINIMUM STAY REQUIREMENT - SEABREEZE 4 Bedroom 3 Bath with Off Street Parking, Private Heated Pool, Fitness Center, Gorgeous!! A warm color scheme and meticulous design details lend an elegant tropical ambience to this spacious four bedroom, 3 bath home located in the 'Sanctuary' on the... View all property information
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    4 of 5 stars Reviewed 2 May 2014
    We rented Seabreeze for a month! It was in the Golf Course a gated community. It was a great home away from home. Very comfortable, stocked well. Had a few glitches with the...
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    $346
    / Night
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    1 / 25
    4.5 of 5 stars (15) Very good
    Key West
    Apartment - 
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (15) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    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 tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security... View all property information
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    5 of 5 stars Reviewed 11 December 2014
    Amazing condo ! Great Staff ! Beautiful place with comfy beds and all the comforts of home and then some ! Hot Tub !!! Full kitchen w/washer and dryer. Gated parking and 2 pools...
    5 of 5 stars Reviewed 22 August 2014
    I have stayed in this location once before. They have upgraded the flooring and it looks great. The pool is quiet and relaxing. The unit sits back from Duval Street so there is...
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    $256
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    1 / 26
    3 of 5 stars (1) Average
    Key West
    Apartment - 
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Sunrise Suites Resort is an island paradise. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair and bask by our lagoon-shaped pool surrounded by lush tropical foliage where you can let your cares melt away. Please take a moment to look through our site at our many... View all property information
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    3 of 5 stars Reviewed 24 November 2014
    When we arrived they did not have our reservation in their system eve though I had prepaid. I booked through a third party. I showed them my receipts and they put us in a room...
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