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Vacation Rentals near Southernmost Point

Whitehead Street, Key West, Florida 33040
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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 86 Rentals in Key West
    Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach1 / 19
    (1)Excellent
    0.1 miles from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH1 / 61
    (9)Excellent
    0.1 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Seaside Place Key West FL 5 Bedroom House 4 Baths1 / 57
    (41)Excellent
    0.0 miles from Southernmost Point
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Casa Grande1 / 25
    (5)Excellent
    0.2 miles from Southernmost Point
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Washer
    • Parking
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 14, 2018
    5 couples, one house, and we could not have asked for more. Everyone had their own space and tons of space to share. The pool was amazing, the house was clean. Everyone loved...
    Reviewed May 6, 2015
    This was our second year at Casa Grande and I recommend highly if you're a group of 8-12 people. Beautiful location near 1100 block of Duval. Nice large pool in backyard...
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    About this property
    Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions! 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...
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    Key West, Florida Keys
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool1 / 42
    (5)Very good
    0.1 miles from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Yard
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 1, 2018
    Just one building off of Duval so you are literally steps from the action and all the conveniences that Duval offers. Yet, the house it located on a short dead-end alley...
    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...
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    About this property
    Bahama House Privacy meets convenience at this beautiful Key West vacation rental, which features a two-bedroom, two-bathroom home, a separate studio cottage, a private pool, and room for up to eight guests. The family dog is also welcome to join you for an additional nightly fee. This recently...
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    Stock Island, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Dog-friendly home in a quiet neighborhood w/ shared pool & private hot tub!1 / 37
    (7)Very good
    0.2 miles from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2016
    We rented the entire complex for our wedding. While my husband and I did not stay in this particular cottage we did see the interior and this was used as my "bridal...
    Reviewed May 21, 2015
    We booked this rental through Flipkey. The pictures didn't really show how nice it is. It's not the Ritz, as the other review says, but really very nice. Good kitchen with...
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    About this property
    Tropical Village Hideaway Treat your group to a tropical getaway at this dog-friendly Key West retreat. Featuring room for up to six guests and a cute canine companion (for a small nightly fee), street parking, a private hot tub, and a shared pool, your vacation promises to be one to remember....
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    Stock Island, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Deluxe, ground-floor studio w/ view of the courtyard and pool - close to shops1 / 26
    (14)Very good
    0.1 miles from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Washer
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 19, 2015
    The setting is very secluded yet only two blocks from Duval Street. The main house is very nice with 2 bedrooms, 2 baths, kitchen, dining and living room. A porch surrounds 3...
    Reviewed June 4, 2015
    By far the best part about our stay was the pool. It was so great to have somewhere to relax while we were in Key West. That's the whole point in going! The pool was the perfect...
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    About this property
    Papa's Hideaway #3 - For Whom the Bell Tolls Enjoy that next romantic getaway in Key West at this adorable and colorful ground-floor studio complete with a well-equipped kitchenette and view of the well-maintained courtyard and shared heated pool. Please note that off-street parking is available at...
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    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Bright condo w/ private hot tub & shared pool - close to shops & beaches1 / 25
    (16)Very good
    0.2 miles from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Patio
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 12, 2017
    We couldn't have been happier with Casa Havana for our first trip to Key West! The 2bdr/2bth set up was perfect for 2 couples, and the location couldn't be beat! Easy to walk...
    Reviewed December 10, 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...
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    Casa Havana * Duval Square R22 Find a cool, comfortable retreat at this dog-friendly Key West condo, a well-equipped getaway with a private deck and balcony, access to a community swimming pool, and a wonderful location near the heart of the old town. This condo sits among tropical gardens in...
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    Stock Island, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    0.1 miles from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pescado Penthouse On Duval Stay in style in the heart of Key West, where your balcony overlooks the colorful main drag! This home has dog-friendly accommodations for a small nightly fee. This condo faces historic Duval Street, where you'll find some of Key West's most exciting shopping and...
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    Stock Island, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
    Peaceful, dog-friendly home in a residential neighborhood w/ a shared pool1 / 36
    (3)Average
    0.2 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Private Yard
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information.I did not stay in this particular cottage but our guests had rave...
    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...
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    About this property
    Tropical Village -Southern Cross Treat the whole family to a seaside adventure when you book your getaway to this dog-friendly Key West cottage. Boasting a prime location close to beach activities and attractions, as well as a shared pool, this home welcomes up to six guests and a canine companion...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Colorful condo w/ deck, balcony & shared pool - near downtown & beaches1 / 39
    (24)Very good
    0.2 miles from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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    About this property
    Casa Cubana * Duval Square R14 Find a colorful, comfortable escape in the heart of Key West at this two-bedroom condo, where you'll enjoy a private deck and balcony, a community swimming pool, and easy access to beaches and downtown. This well-appointed condo sits in the heart of historic Key...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Penthouse w/ private hot tub & shared pool - close to beaches1 / 35
    (28)Very good
    0.2 miles from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Balcony
    • Patio
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 13, 2017
    My weekend stay was fabulous. Condo location was perfect. Beautiful updated kitchen and living room. Bedrooms were perfect. I would 100% recommend.. Look forward to coming back.
    Reviewed September 16, 2015
    Very nice place in a great location. Close to everything and very convenient. Staff was excellent, place was clean and service by the concierge was top notch. I would stay...
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    About this property
    Duval Square Penthouse R19 Surround yourself with the historic charms of Key West at this dog-friendly penthouse, a spacious South Florida escape with a private hot tub, a deck and balcony for evening cocktails, and access to a lovely community swimming pool. You'll find this comfortable condo...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Condo in historic district w/shared hot tub  - 2 blocks to ocean, dogs OK1 / 28
    (24)Very good
    0.1 miles from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 22, 2015
    We just spent a week at SMR and really enjoyed our stay!Close to duval without the noise! We could hear some live music from la te da one night, but it was nice to sit on the...
    Reviewed November 23, 2014
    Location right on Duval was awesome! We were close to everything! The condo has a great layout. Fully functional kitchen. 2 bedrooms with TVs. Outdoor space with hot tub...
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    About this property
    Southernmost Retreat Here in the heart of historic Key West, you'll have access to a shared hot tub, dog-friendly accommodations, and grill on your backyard patio area, as well as private parking! From here, you're only two blocks from the beach at Fort Zachary Taylor State Park. Duval Street's...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    0.1 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Yellowfin Ledge On Duval Explore Key West with this conveniently located, dog-friendly condo as your home base! Duval Street's famous array of bars, shopping, and eateries is just outside your door. Explore the neighborhood's historic sights like the Ernest Hemingway House, about five blocks...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
    0.0 miles from Southernmost Point
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Ocean Views
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Hueso *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* This four-bedroom Key West home has just what you need for an awe-inspiring Florida beach getaway, including a private heated pool,...
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    Stock Island, Florida Keys
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    0.2 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Cable/satellite TV
    • Private Yard
    • Balcony
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kate's Krawl Off Duval The sunny paradise of Key West beckons, and this dog-friendly home is the perfect place to stay, with a private patio ensuring relaxation is never far away. Located just steps from desirable Duval Street, this home makes it easy to experience all the best attractions in...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Six dog-friendly homes in a quiet neighborhood w/ private pool & hot tub1 / 25
    (1)Excellent
    0.2 miles from Southernmost Point
    12 Bedrooms, 9 Bathrooms, Sleeps 30 Quick View
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    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2016
    We rented out the entire Tropical Village compound for our December 2015 destination wedding. While renting all 6 cottages may not be the "norm," it worked out perfect...
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    Tropical Village If you're planning your next family friendly group getaway or a large family reunion, this grouping of six separate Key West homes is the perfect spot for everyone to spread out and enjoy some privacy in a quiet residential neighborhood. Featuring street parking, a private pool,...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 12 Bedrooms, 9 Bathrooms, Sleeps 30
    Lovely, dog-friendly townhouse w/ private pool, full kitchen & beach access1 / 47
    (21)Very good
    0.2 miles from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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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    About this property
    Island Oasis You'll settle into island life instantly at this two-bedroom, two-and-a-half-bathroom townhouse in Key West. With a private pool and lush garden in the backyard, a full kitchen, and a great location near the beach, comfort is never far away from your explorations. Located on the...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    0.1 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Private Yard
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Louisa's Garden Book this wonderful ground level Old Town cottage with all of the comforts of home and start your vacations off on the right foot! It features an open floor plan with doors that open to back patio to create indoor/outdoor living. Kick back in the living room area and watch your...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Amelia Home1 / 24
    (57)Very good
    0.2 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 13, 2019
    We enjoyed every thing about this house. Close enough to Duval. The pool was perfect size for 4 people.
    Reviewed February 4, 2019
    Amelia House was a lovely place to stay. Very clean and an excellent location! The heated pool was perfect as it was a bit chilly when we stayed. We walked everywhere from here.
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    About this property
    After a long day cool off in your private pool, enjoy cold Mojitos on the covered porch and cook up some fresh grouper on the grill! Welcome to your dream vacation home! The Amelia home is a 2 bedroom 2.5 bath retreat with sparkling private pool that is only four blocks from the Atlantic Ocean...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Condo on Duval w/shared hot tub  & private parking - dogs OK1 / 28
    (34)Very good
    0.1 miles from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 4, 2010
    Actually stayed in "Heather's Villa" rather than Buena Vista. We've stayed in B.V. before, and it is also equally nice. Heather's is located directly in front of B.V...
    Reviewed July 5, 2009
    We loved staying there. Great for a reconnection of my husband and myself after 12 years of marriage. Great location, safe and private. Walked or rented moped to get where we...
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    About this property
    Duval Hideaway Unwind in the heart of Key West's historic district with a dip in condo's hot tub ! The back patio here offers room to grill out and relax with your group after a long day enjoying all the island has to offer. This suite is located on historic Duval Street, where you'll find some...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Charming, dog-friendly home in a residential neighborhood w/ shared pool1 / 29
    (8)Very good
    0.2 miles from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information.This is what my (now) husband and I used during our stay.It was...
    Reviewed April 3, 2016
    This place was very private, tropical, had a very nice pool with about 5 or 6 apartment/houses surrounding the pool that you hardly knew were there. They were hidden with...
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    About this property
    Tropical Village - Poolside Paradise If you're looking for the perfect romantic escape for your next getaway, then look no further than this romantic Key West cottage. Featuring room for two guests to enjoy a shared pool and a location that puts you within easy reach of all of the local...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Island-themed, dog-friendly home in a residential neighborhood w/ a shared pool1 / 24
    (2)Very good
    0.2 miles from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 22, 2016
    Love the place! Location was good. There was an issue with ants in the kitchen. Also, I was issued 3 keys and 1 of the keys was not for our place. Changed the key with...
    Reviewed April 21, 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information.I did not stay in this particular cottage but our guests had rave...
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    About this property
    Tropical Village Utopia Get away from the stress of the daily grind with a trip to this contemporary Key West home. Offering street parking, access to a shared pool, room for up to four guests, and a charming island-themed ambiance, this home will make it easy to slip into vacation mode. The family...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.1 miles from Southernmost Point
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Duval Street Retreat Stay in style in the heart of Key West's historic downtown, where you're steps from the beach and all Duval Street has to offer! Your back patio houses a private hot tub, dog-friendly accommodations, and grill, perfect for lounging with the group after a long day of play....
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    Tropical Dreaming1 / 24
    (61)Very good
    0.2 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 8, 2020
    I visited this property and had great expectations however i was really surprised to see poor quality of food and gym services.
    Reviewed October 3, 2018
    This house has a great location and the floorplan is wonderful for 2 couples. The main issue is that proper maintenance is spotty and the property manager is not checking up on...
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    About this property
    Do not look any further! Your perfect vacation home rental is right here! Offering private pool with lounge chairs and covered outside porch. You can also bring your Fido! A distinctive private Key West vacation home with sparkling private pool, Tropical Dreaming is the classic example of the...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Cozy, dog-friendly retreat w/ shared hot tubs, patio, great location in Old Town1 / 29
    (2)Excellent
    0.1 miles from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Grill
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 25, 2015
    This place was perfect for our vacation needs. It was close to everything, and the places a bit further away totally doable by renting bikes for the week. We cooked some meals...
    Reviewed August 28, 2014
    This was a last minute booking for us.. we had no idea what type of room we would be getting. Boy were we surprised! The gate is a little hard to find at first and you begin...
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    About this property
    Osprey Suite Take a break from the ordinary with a visit to this tropical hideaway in the heart of Key West's historic district! Ideal for a romantic getaway, this suite promises comfort, space to relax, and a prime location in Old Town. The family dog is also welcome to join you for an additional...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    0.1 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gingerbread *Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. Take advantage of all that Key West has to offer from the incredible location of this adorable Key West home. This home features a full...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.1 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kingfish Keep On Duval Experience the best of Key West's historic district from the comfort of this condo! An upstairs balcony gives you a bird's eye view of the town, and you'll be steps away from shopping, dining, and the beach. Guests staying at this suite will experience historic Duval...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
    Duval Sea Turtle1 / 24
    (49)Very good
    0.2 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    • Balcony
    • Washer
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 28, 2016
    Just returned from a stay and this property exceeded our expectations. It was a great location in easy walking distance to everything on Duval. The unit was spotlessly clean...
    Reviewed July 4, 2014
    Great Location to enjoy all Key West has to offer. CVS for stocking up on snacks, alcohol, basic groceries is right next door. It was great to have 2 baths upstairs and 1/2 down...
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    About this property
    Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea Turtle townhome within easy walking distance to everything! Meticulously decorated with art from local galleries and artists, you’ll be greeted by the super-sized sea turtle...
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Tropical Key West studio w/ shared pool - near beaches & Duval St.1 / 25
    (8)Very good
    0.1 miles from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 25, 2015
    Clean, quiet, beautiful garden pool, well managed, prompt shuttle, fun to watch the iguanas marching thru and sun bathing in the palm trees. Locations is great, close to Duval...
    Reviewed July 30, 2014
    Papa's Hideaway is located on a quiet side street, a block away fromKey West's main drag, Duval Street, and a two-block walk from the"Southernmost Point" landmark: a...
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    Papa's Hideaway #4 - Islands in the Stream Plan a romantic getaway for two to Key West at this quaint studio rental complete with a well-equipped kitchenette, furnished patio, and access to a shared swimming pool, well-maintained tropical courtyard, and sundeck. This complex is located in a quiet,...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Old Town condo w/private hot tub & shared pool - walk to Duval St!1 / 29
    (36)Very good
    0.2 miles from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Hot Tub
    • Cable/satellite TV
    • Balcony
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 9, 2016
    My husband and I stayed at this condo for 2 nights with another couple. The location was great. Although we were near the main street, this unit (R9) was quiet (except for the...
    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...
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    About this property
    Casa Caribe * Duval Square R9 Bask in the allure of old town Key West at this sunny condo, where you'll have a private hot tub and deck, a community swimming pool, and enviable access to beaches, shops, and wonderful restaurants. Located mere steps from Duval Street and verdant tropical gardens,...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    1.1 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    • DVD Player
    • Cable/satellite TV
    • Housekeeping Included
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Cozy, dog-friendly suite w/ shared hot tubs, grill, and patio space to relax1 / 27
    (3)Excellent
    0.1 miles from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Grill
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 23, 2016
    My Daughter and I stayed in Ibis Suite.We Loved the location and the secluded quietness of our suite.The Cuban coffee shop, the Sandwich shop, the Grocery store, the Trolley...
    Reviewed June 2, 2015
    My friends and I stayed at Ibis this past January (all in our mid 20's). I thought I reviewed this property then, but apparently I did not. It was our first trip to Key West and...
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    Ibis Suite Ibis Suite offers visitors a prime location in Old Town Key West, great amenities, and space to relax. Top off your visit with soaking time in one of the property's hot tubs, and you're well on your way to an optimal Key West experience. Here, you're a few blocks off of famous Duval...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Tropical family-friendly home w/private pool, 1/2 block from Duval St. - dogs ok1 / 49
    (50)Very good
    0.1 miles from Southernmost Point
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
    • Cable/satellite TV
    • Private Yard
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 16, 2014
    The rental is great and in an excellent location. We had a group of 6 and had no issues. Note: unlike some rentals there is nothing in the house if you plan to cook. You...
    Reviewed July 24, 2014
    Everything was easy and perfect check in wise. Rooms were clean. Will stay here again. Walked to all bars and loved the tall ceilings.
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    About this property
    Tropical Retreat Immerse yourself in the island lifestyle when you book this Key West accommodation, comprised of a two-bedroom house and a separate one-bedroom pool house. Featuring a private heated pool at no additional fee, a private parking spot, and an outdoor shower, this home gives you the...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Spacious, dog-friendly rental w/ three hot tubs, near Duval Street and the beach1 / 49
    (2)Very good
    0.1 miles from Southernmost Point
    6 Bedrooms, 6 Bathrooms, Sleeps 24 Quick View
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    • Patio
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 4, 2017
    This property is private and has the benefits of a kitchenette and a hot tub. Accommodations are very average--the room is no frills and could use updating and some new...
    Reviewed May 26, 2016
    Was a bit frustrated after arriving to realize the office that rents these was not on site but at 1075 duval suite 22..I had booked through booking. Com and at first they...
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    About this property
    Southernmost Sanctuary Gather your group at this festive property, home to three private hot tubs, deck space, multiple kitchenettes, and six bedrooms for up to 24 people. The family dog is also welcome to join you for an additional nightly fee. You're about a block away from Southernmost Point,...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 24
    Quiet, dog-friendly getaway in a residential neighborhood with a shared pool1 / 24
    (4)Excellent
    0.2 miles from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information.I did not stay in this cottage but our guests had rave reviews and I...
    Reviewed March 5, 2015
    My family and I stayed at Toon Hall the last week in February and had a blast. The home is located close to Higgs Beach, a few blocks away, and a few blocks from Duvall St. The...
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    Tropical Village - Toon Hall Grab your sunglasses, your beach towel, and charge your camera for a visit to this Key West home, once the winter home of Pulitzer Prize-winning cartoonist Jeff MacNelly. Offering a family-friendly atmosphere and a pristine shared pool, this home gives you the chance to...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Cute, dog-friendly condo w/ shared hot tub in the heart of historic Key West!1 / 25
    (2)Very good
    0.1 miles from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 5, 2014
    The room was a nice size for two friends. It was not fancy, but clean and well equipped. Another plus was the front porch where we sat and people watched while having coffee or...
    Reviewed July 25, 2014
    The Egret Studio is very close to the Southernmost Point and next door to a Cuban cafe, so I had coffee there every morning. The studio is very clean, well appointed and we...
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    About this property
    Egret Suite Settle in at this conveniently located four-person suite, where you'll have access to a shared hot tub and your own kitchenette! Egret Suite can be rented on its own, or as a part of the entire property for larger groups. The family dog is also welcome to join you for an additional...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    0.1 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wahoo Way On Duval This dog-friendly suite provides everything you need for a couple's getaway in Key West. This home's coveted location on Duval Street means prime access to the town's best nightlife and restaurants, like Nine One Five a few blocks away. You're also a short walk from the beach...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
    Charming studio w/ shared pool, covered patio - a block from shopping and dining1 / 26
    (8)Very good
    0.1 miles from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
    • Washer
    • Terrace
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 13, 2015
    Well, talk about HIGH season. Prices are dear and the lines of cars down the highway get longer each day between Xmas and New Year's. But Key West is a special place, at least...
    Reviewed December 23, 2014
    Stayed for a week before Christmas 2014. I did a bit of research on different properties/hotels, and really wanted to get away from the traditional 'resort' style...
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    Papa's Hideaway #1 - Torrents of Spring Absolutely ideal for a romantic getaway for two, this cozy studio offers a well-equipped kitchenette, a furnished deck, and access to a shared swimming pool at the heart of a beautifully-maintained tropical courtyard. Located just a block from Duval...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Classic Key West cottage featuring shared pool, courtyard, covered front porch1 / 57
    (17)Very good
    0.1 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 27, 2017
    We stayed here after having a rough go of it in Miami and we fell in love. My kids said "Mom we should have stayed here the whole time, this place is awesome." The pool...
    Reviewed September 10, 2015
    Beautifully decorated Old Key West home. Our kids (12, 5) loved seeing the Iguana in the courtyard. The pool was nice to relax in after a day of sightseeing. Beds were...
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    About this property
    Papa's Hideaway - Garden of Eden Part of the Papa's Hideaway complex, this charming, old Key West cottage is an ideal home away from home for that next vacation to the Southernmost Point. Up to six guests can enjoy this recently updated home complete with a high-end kitchen, loads of modern...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.2 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Grill
    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tropical Village - Tropical Cottage Slip into vacation mode as you explore Duval Street and dive into the beach scene when you book your trip to this dog-friendly Key West cottage. Featuring street parking, a relaxing shared pool, and a location that puts you right in the heart of the action, up to...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Charming tropical getaway w/ shared pool, sundeck, and bar - near Duval Street1 / 29
    (4)Very good
    0.1 miles from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Balcony
    • Terrace
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 27, 2014
    Papa's Hideaway is a hidden paradise! It is beautiful and comfortable and close to everything. The bed was extremely comfortable and furnished with everything we needed for a...
    Reviewed March 18, 2014
    Loved the location to everything,walking distance and even had parking included in the cost of rental...made me feel relaxed instantly,loved hanging out at the pool and meeting...
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    Papa's Hideaway #2 - The Sun Also Rises This second-floor studio has a private outdoor seating area and plenty of space for up to four guests. Spend time at home splashing in the shared pool or catch some rays on the sundeck. Located in a residential neighborhood, this rental is just a short...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Dog-friendly beach suite w/ shared hot tubs, kitchenette, patio space, and more!1 / 29
    (6)Average
    0.1 miles from Southernmost Point
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 19, 2017
    We stayed from Monday through Thursday so we expected lower crowds but were we surprised. Check in was easy but at a different location. It was a surprise to have to park our...
    Reviewed December 12, 2015
    First impression was that room smelled clean. Very secluded and minutes from Duval Street. Second night, noticed a lot of critter activity. Small bugs and roaches. Management...
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    About this property
    Seagull Suite Look no further than this homey suite for your next couple's weekend! Take a dip in the property's shared hot tubs, or simply enjoy the fresh air on the patio space outside your doorstep. Seagull Suite situates you walking distance from historic Duval Street's attractions, from...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Dog-friendly Key West cottage with a private hot tub & an unbeatable location!1 / 25
    (10)Very good
    0.2 miles from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Air Conditioning
    • Patio
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 13, 2015
    Great location! 1/2 a block off the main street (Duval) and convenient to everything, but in a quiet dead end street. Private parking! (Hard to park anywhere in the Keys...
    Reviewed January 12, 2015
    Its just a few steps away from where all the actions is. Considering the location, it is actually quiet at night. We got ourselves lock out while drinking and partying at the...
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    About this property
    Amelia House Spend your vacation days snorkeling in the clear coastal waters and strolling the streets of downtown Key West when you stay at this three-bedroom, two-bathroom cottage, which also features a private hot tub and one reserved off-street parking space. The family dog is also welcome to...
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    Location Information
    Stock Island, Florida Keys
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval1 / 24
    (87)Very good
    0.1 miles from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    • Internet Access
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    • Patio
    • Housekeeping Included
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Luxury 2/2 condo In Heart Of Key West With Lagoon Pool. Monthly rentals only1 / 23
    (4)Excellent
    0.5 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Balcony
    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    'TORTOISE SHELL II' ~ Comfortable, Modern Condo Two Blocks from Duval!1 / 15
    (5)Excellent
    0.8 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Air Conditioning
    • Washer
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Attitude Key West (2 Bikes and Wireless Internet)1 / 49
    (93)Excellent
    0.6 miles from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • DVD Player
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    • Patio
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!1 / 50
    (7)Very good
    0.6 miles from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
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    • DVD Player
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Truman Annex, two blocks from Duval1 / 27
    (42)Very good
    0.8 miles from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • DVD Player
    • Air Conditioning
    • Internet Access
    • Patio
    • Shared Outdoor Pool (Unheated)
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    • Washer
    Suitability
    Pet friendly
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    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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