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Pet Friendly Rentals in Key West, FL

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    Travelers to Key West are booking March dates now. Secure your vacation rental today, and have the perfect trip.
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    1 / 24
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Terrace
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    • DVD Player
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    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities... View all property information
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    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Washer
    • Balcony
    • Outdoor Dining Area
    • Porch
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    About this property
    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! The property is completely private and safe, surrounded by a 6 foot gated fence and tropical landscaping. Due to local zoning laws we... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4 of 5 stars (20) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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    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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 20, 2013
    I chose the Pelican Landing due its proximity to Duvall Street and the ability to secure the rental for daily rates. The unit was spacious and had a lot of accommodations within...
    5 of 5 stars Reviewed June 16, 2013
    I was very happy and impressed with the conda that I stayed at,,, It was very clean,spacious and had very nice view
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Patio
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is for the guest that would like to experience the yachting lifestyle without ever leaving the dock. Staying at the dock allows you to come and go as you please whether it be scootering around Wilmington town or shopping, eating and drinking your way down to the board walk on front street .... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 12
    5 of 5 stars (3) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Grill
    • Air Conditioning
    • Porch
    • Outdoor Dining Area
    • Balcony
    • Wi-Fi
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed February 10, 2015
    Absolutely loved our stay. Owners were great to work with. Furnishings were warm and inviting. Would definitely stay again!
    5 of 5 stars Reviewed October 31, 2014
    First of all, this hotel is awesome! We went as a group of 8 women and I was thrilled that we only needed two rooms and they were side by side! Had a balcony, and plenty of room...
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    1 / 23
    4 of 5 stars (19) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $300
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    • DVD Player
    • Grill
    • Satellite TV
    • Balcony
    • Internet Access
    • Shared Outdoor Pool...
    • Air Conditioning
    • Terrace
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed December 15, 2015
    Could be a great place . Needs a good deep cleaning and friendlier and more helpful women working in the office. Was there for 4 days with kids in November with no pool heater...
    5 of 5 stars Reviewed July 18, 2013
    I used to live in Key West and have had friends stay here before. I was excited to see the new renovations they had done. The room was beautiful and clean and our stay was great...
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    1 / 26
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Internet Access
    • DVD Player
    • Grill
    • Satellite TV
    • Air Conditioning
    • Balcony
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention to... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 30, 2013
    What could be better in Key West than your own pool, adorable kitchen and updated baths, and a great location, a few blocks from Duval. Kw Vacation Rentals couldn't have been...
    5 of 5 stars Reviewed December 23, 2013
    The house is my perfect idea of what a Key West Conce Cottage should be. With Dade County pine walls, heated pool, all modern conveniences and perfect location for quite and easy...
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    1 / 12
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    $350
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    • Housekeeping...
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Patio
    • Satellite TV
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Relax in paradise amongst all the comforts of home in the Sailor House, a proud member of Andrews Inn & Garden Cottages. Just a half a block off the world famous Duval Street, the Sailor House offers the ultimate in privacy and luxurious island living. Families and couples traveling together rave... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed July 7, 2015
    We went over the 4th of July weekend with a group of friends. Location is still amazing. The major concern was the it never felt as if the AC was cold enough. I am wondering if...
    4 of 5 stars Reviewed April 24, 2015
    Cute two story Key West cottage. Located blocks away from Duval, but yet quiet. Good times were had at the Jacuzzi and the top patio. The swing on the top balcony was nice and...
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    1 / 30
    4 of 5 stars (39) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    $500
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    • Terrace
    • Satellite TV
    • Shared Outdoor Pool...
    • Air Conditioning
    • Internet Access
    • Grill
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed November 8, 2013
    We had seven guys from four states converge here for my bachelor party, and I cannot say enough about this place. I didn't experience any of the symptoms of what the bad reviews...
    5 of 5 stars Reviewed September 3, 2013
    We were not vacationing; we were working and the accommodations were very good for us. We wish we had more time to enjoy it. Thanks for being so accommodating and helpful! Tammy...
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    $5,500
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    • Air Conditioning
    • Satellite TV
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    • Pet-friendly
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    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ***BRAND NEW POOL COMPLETED SEPTEMBER 2015*** Tucked into a quiet residential neighborhood, this renovated home is the perfect getaway for a family or group of friends looking to experience the Key West island life! This 3 bedroom home is on Patricia St, just a block from the scenic biking bath... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    3 of 5 stars (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    $288
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    • Pet-friendly
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    • Elder access
    • x
    • ?
    About this property
    Part of TROPICAL VILLAGE Southern Cross: Lounging next to the gorgeous shared pool or sitting in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 7, 2014
    The property was clean, the kitchen was equipped with all the necessities, great private porch and shared pool. Location is great - just a couple blocks from Duval and a 15 minute...
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    1 / 29
    4 of 5 stars (9) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Satellite TV
    • Patio
    • Air Conditioning
    • Terrace
    • Balcony
    • Shared Outdoor Pool...
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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 on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location. Enjoy nearby... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed May 15, 2015
    I stayed here with four of my friends and the location was wonderful close to restaurants close to clubs and only a half a block off of Duval. this is a wonderful place and I...
    5 of 5 stars Reviewed July 4, 2009
    My husband and I stayed here with my parents and had a really wonderful time. The house was adorable, clean and had everything we needed. It was close to all the action on Duval...
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    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Satellite TV
    • Patio
    • Parking
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including a... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed April 10, 2014
    The place was really nice and the staff was very easy to work with. It was a very good vacation and would definitely like to stay there again.
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    1 / 32
    4.5 of 5 stars (34) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Satellite TV
    • Terrace
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Caribe is a second story paradise just steps from the sights, sounds and excitement of world-famous Duval Street. Lush and tropical gardens surround this beautiful... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed January 19, 2015
    We've been to Key West a number of times, but never in January. We're not party animals or lovers of noise, so I knew to avoid the Mallory Square end of things. This condo was...
    4 of 5 stars Reviewed November 11, 2014
    Casa Caribe was a wonderful place for us to stay while in KW. It's on the quiet end of Duval so don't be deterred by the address, only a few blocks from the Southernmost point...
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    1 / 26
    4.5 of 5 stars (23) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Balcony
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    • Shared Outdoor Pool...
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    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    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 stars Reviewed April 7, 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 stars Reviewed August 6, 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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    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    • Internet Access
    • Waterfront
    • Patio
    • Air Conditioning
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    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** a passport tucked away off of mile marker 15. While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Around the back of the... View all property information
    Location Information
    Key West, Florida Keys
    1 / 25
    4 of 5 stars (37) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Patio
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    • Pet-friendly
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    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • 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 stars Reviewed December 15, 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 stars Reviewed December 11, 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 / 22
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $180
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    • Terrace
    • Internet Access
    • Washer
    • Parking
    • Air Conditioning
    • DVD Player
    • Balcony
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to start your day of... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    5 of 5 stars (4) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    $528
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    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene hideaway is just moments away from Duval Street and the most exciting spots the southernmost... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed September 9, 2015
    This was perfect for our family and dog!! yes dog and a big one!!Very modern kept very well plenty of room!! All around great!! When you get there you will see why the word...
    4 of 5 stars Reviewed September 8, 2015
    House set up to be very welcoming and COOL. TVs and bathrooms in every room, washer/dryer, kitchen with cooking equipment. Only problem I found was there were no full length...
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    1 / 26
    4.5 of 5 stars (20) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    The beaches of the Atlantic Ocean are less than a 7 minute blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed December 11, 2014
    It was our first time in Key West and, well, you just never know. I got this one spot on though. The decor is fun. the kitchen is very functional. The two master suites were...
    5 of 5 stars Reviewed October 25, 2014
    The townhouse is excellent. Location is also a huge positive. Clean and updated. Wifi was easy to access.
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    1 / 22
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • Child-friendly
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    • Elder access
    • x
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    About this property
    The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch Cottage. It is a perfect example of turn-of-the-century island architecture. This adorable two bedroom cottage, each with queen bed and TV (the master has a large flat screen), two full baths and queen sleeper-sofa is... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 13, 2014
    The Bahama House looked just like the pictures and the location was just as advertised-convenient!! The staff at Key West Rentals were quick to respond to issues with pool and...
    5 of 5 stars Reviewed July 25, 2014
    I can say this very simply, this is exactly what you picture in your mind when you think of a quaint bungalow in Key West, except more luxurious. Top notch value.
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Internet Access
    • Patio
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    • DVD Player
    • Balcony
    • Grill
    • Air Conditioning
    • Washer
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    The master bedroom has a queen sized bed with a feather mattress topper to experience a floating cloud effect. It has cable flat-screen TV, DVD/VCR, and a balcony where you can sit (take director's chairs from bedrooms) for morning coffee or evening cocktails. The customized closet has a set of... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 37
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    $345
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    • Patio
    • Private Outdoor...
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    • Washer
    • Air Conditioning
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
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    About this property
    AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Key West vacation you have been seeking. Tucked away in one of the most interesting neighborhoods in the historic... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 2 Bathrooms, Sleeps 2 | Quick View
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    Minimum 90 day stay requirement- Las Salinas is well maintained and has a beautiful community pool. Offers covered parking. There is a shared swimming pool.Located in New Town featuring 1 bedroom with a queen sized bed and one bathroom. The unit has a private balcony and offers covered parking.... View all property information
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    Key West, Florida Keys 33040
    1 / 32
    5 of 5 stars (2) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    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
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed November 11, 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...
    5 of 5 stars Reviewed December 22, 2014
    This was our second extended stay in this unit and we absolutely love it! You can't beat the location or the privacy of the unit. It's a perfect unit for two! There's a few...
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    1 / 26
    4 of 5 stars (4) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** The spacious living room/dining room features a with large flat screen TV and DVD player. Living room French doors open up into the private deck which features outdoor seating and a Gas BBQ Grill, making your... View all property information
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    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 31, 2014
    We had a wonderful time staying in Key West. The condo location was perfect. We walked everywhere. The beds were comfortable, and although the kitchen is very small, it was...
    3 of 5 stars Reviewed March 15, 2014
    We have stayed all over Key West over the last 20 years and always liked the Truman annex area so decided to try it out. Well this is actually in Shipyard Condo area next to...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 stars (15) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Part of ALMOST SOUTHERNMOST RETREAT This Truman Avenue home is the perfect location, located between Duval Street and Whitehead St. The style is common throughout the islands. Our shotgun was renovated in March, 2008. Located in among a row of identical cigar-maker cottages, this gem features a... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 1, 2014
    Our first visit to the Keys celebrating our 28th anniversary with our adult children, (3 couples) this historic cottage slept all 6 of us very comfortably; in fact, the most...
    5 of 5 stars Reviewed February 4, 2014
    We have stayed at this property on previous visits to Key West- it is a great location- close to everything and has plenty of space. Easy to cook at home if you don't want to go...
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    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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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    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Key West, Florida Keys 33040
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Part of Banana's Foster Guest House This spacious 2 bedroom apartment takes up the first floor of this historic home. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front entrance with sweeping front porch over Caroline Street- this... View all property information
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    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ***Recently updated 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... View all property information
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    Key West, Florida Keys 33040
    4 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Havana Oasis is comprised of two of our most popular homes! Island Oasis The beaches of the Atlantic Ocean are less than a 7 minute blocks away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey.... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    4.5 of 5 stars (22) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed May 30, 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...
    5 of 5 stars Reviewed December 23, 2014
    Trying to pick out a vacation rental in Key West is like finding a needle in a haystack. You just never know what you are going to get. I did a lot of research before we settled...
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    1 / 30
    4.5 of 5 stars (6) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Part of ALMOST SOUTHERNMOST RETREAT Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed July 25, 2014
    This is our second time staying in this property. We stayed here again because the property manager & his team were fantastic, the property was very clean and it was a great...
    5 of 5 stars Reviewed June 6, 2014
    Very clean, looks recently redone. Great set up, plenty of room for the six of us. Most comfortable bed ever. Literally steps from Duval St. I would definitely stay here again.
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 / 30
    4.5 of 5 stars (4) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors,... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed April 10, 2014
    Location of Tobago house is excellent if you like to be close to restaurants, beach, and all that key west has to offer. Leave your car at home as parking is difficult. The house...
    4 of 5 stars Reviewed March 12, 2014
    We were at Tobago House for the month of February 2014. It is absolutely wonderful !! I will say that I would have preferred if everything had been tested out before we got...
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    The Beach Boys on one of their many trips to Key West (they are Mojito buds with Jimmy Buffett) stayed at our vacation rental called Havana Hideaway, where they wrote the song Kokomo - according to a very reliable source at the Pink Cab Company. This vacation rental is a modern two-story, built in... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    My Sunshine Luxury Suite is an upscale property located in Key West, an island paradise. Sunshine Suite provides the luxury and convenience of your own condo home just 90 miles from Havana. Surrounding the resort, you will enjoy lush tropical foliage and amenities such as our tennis court, gym... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 28, 2014
    fabulous condo on a very secure property close to the beaches. Roosevelt Blvd is within walking distance and has a sidewalk large enough for walking and biking along the ocean...
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
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    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Beautiful Getaway Spot w/ Pool! Boardwalk Loft is the perfect getaway spot for families, or for individuals that just need some peace and quiet. The interior exudes elegance from top to bottom. You will fall... View all property information
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    Key West, Florida Keys 33040
    1 / 54
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    About this property
    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    4.5 of 5 stars (6) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    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
    Location Information
    Key West, Florida Keys 33040
    3 of 5 stars Reviewed 3 days ago
    We usually stay at the Tropical Inn and thought we'd try someplace new. Terrible mistake. From the disorganized check in to the lack of attention we received we won't be...
    3 of 5 stars Reviewed 2 weeks ago
    The location is excellent and the photos accurately show the room. The main issue is the bathroom as there is no privacy. All that separates you from the kitchen/bedroom is a...
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    1 / 24
    4 of 5 stars (5) Very good
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Part of TROPICAL VILLAGE Where else can you find resort style accommodations at motel pricing? Poolside Paradise @ Tropical Village, features all the amenities needed for a quick weekend getaway vacation at an affordable nightly rate. Once the winter vacation suite of Pulitzer Prize winning... View all property information
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed June 29, 2015
    We are still here but had to write already. This place is just what tit says it is. We highly recommend this cottage and will come back. It's like 6 cottages all together with a...
    5 of 5 stars Reviewed January 14, 2015
    Wonderful location, slightly away from the hustle and bustle of Duval but only a short walk to many restaurants and bars. And only a 5 minute walk to a public beach! Simple and...
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    1 / 30
    4.5 of 5 stars (21) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    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 stars Reviewed December 8, 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 stars Reviewed November 20, 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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    5 of 5 stars (25) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    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! The bedroom is decorated in rich tropical colors. A writing desk and chair... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed October 8, 2014
    Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
    5 of 5 stars Reviewed August 19, 2014
    My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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    1 / 20
    4.5 of 5 stars (6) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels lays the Paradise Suite. Paradise Suite (renovated for January 2013) is a bi-level suite with one bedroom... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed March 4, 2014
    Nice rental in very pretty courtyard. Friendly people. Very central location for all restaurants and shops. Kitchen could have been better equipped, eg no can opener.
    5 of 5 stars Reviewed January 10, 2014
    Great lodging! Beautifully decorated and maintained, amenities way beyond what is expected! Would highly recommend staying here!
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