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Holiday Rentals near Southernmost Point

Whitehead Street, Key West, Florida 33040
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    All 145 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 / 114
    (41)Excellent
    0.0 miles from Southernmost Point
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok1 / 28
    (2)Very good
    0.4 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 October 2018
    We were very pleased to locate this little home with a shared pool in the heart of the historic district. We were a group of 4 so we were looking for a clean, comfortable, and...
    Reviewed 7 March 2017
    Clean, quaint, and comfortable. The office help was great, and cleaning service was good. This is close to all of the action while maintaining a peaceful night's sleep.
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    About this property
    Poolside Retreat Up to four guests can enjoy all the fun of Key West at this updated home complete with a shared pool with waterfall, and lush, outdoor seating area. As an added bonus, this home comes with private, off-street parking for one vehicle - a real luxury in the Keys! Dogs are allowed...
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    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Conch Haven Old Town 1/1 MONTHLY Rental1 / 16
    (5)Very good
    0.3 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Grill
    • Porch
    • Balcony
    • Air Conditioning
    • Internet Access
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 February 2020
    We have been spending at least a month in Key West every winter for 6 years, usually on our boat. This year we rented this property and really enjoyed it. It is furnished with...
    Reviewed 23 September 2019
    Two months is not enough for me, would like to live there.This is my second year I stay at this house with family visiting couple of times.The owners Stephanie an Donna are...
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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 ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.2 miles from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Ocean Views
    • Parking
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
    0.3 miles from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Terrace
    • DVD Player
    • Washer
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Key Escape Escape to the Florida Keys for a relaxing vacation in this three-bedroom, two-and-a-half bath home for eight (six comfortably) with a private pool and walking distance to the beach and Duval Street. And your favorite canine friend is also welcome for a small nightly fee. This rental...
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    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    The Mermaids House, Historic Old Town Key West1 / 38
    (36)Excellent
    0.4 miles from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2016
    The Mermaid's House has an ideal location, half a block off Duval St and almost directly in the middle of both coasts so easy access to view sunrises and sunsets. The short walk...
    Reviewed 18 December 2015
    Let me start by saying I don't think I've ever stayed at a vacation rental so thoughtfully set up with everything a guest could possibly need. Kudos to Barbara! I loved the...
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    About this property
    Private Historic Bahama Conch Home in Old Town Key West. Fenced in with large tropical private quiet yard. Hundred year old trees to relax under in the hammock or lounge in the comfortable outdoor furniture for a respite from a day of touring.Great place to have a barbecue or read a book ,do yoga...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Casa Grande1 / 25
    (5)Excellent
    0.2 miles from Southernmost Point
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 October 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 6 May 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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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    ** Steps from Duval 1 Bedroom Townhouse in great complex Hidden secret **1 / 27
    (13)Very good
    0.3 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    • Balcony
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2015
    My (adult) daughter and I drove down to Key West for 4 days/nights - I had only been there once; she had never been there. We are from the midwest - it was hard to choose a...
    Reviewed 18 August 2014
    This small townhouse was absolutely the most convenient thing we could have asked for in Key West. 1/2 block off Duval Street at Truman. We literally parked the car and walked...
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    About this property
    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.3 miles from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Galleria - Andy's Attic Take your romantic getaway at this bright studio condo in the heart of Key West's historic Old Town! Free WiFi, a deck, and a kitchenette will have you feeling right at home less than a mile from the beach. Visit Fort Zachary Taylor State Park & Beach, about a mile...
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    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    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 21 April 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 21 May 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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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    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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    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Private Garden
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 November 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 13 October 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Couple's dog-friendly getaway with central location and access to a shared pool1 / 26
    (39)Very good
    0.3 miles from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 March 2015
    I cannot say enough great things about this place. There are 6 duplexes totaling 12 2 story cottages. In the center of all the cottages is a communal area considering of a...
    Reviewed 28 February 2015
    The pictures of the Bermuda Suite are better than the reality, but it is not bad. It is in a gated courtyard complex and the location is ideal. We were able to walk everywhere...
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    About this property
    Old Town Garden Villas - Bermuda Suite Book your romantic escape to this dog-friendly Key West home. With access to a shared pool and a great location on Duval Street, you'll be able to slip into vacation mode in no time. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Contemporary dog-friendly cottage with easy beach access and shared pool1 / 31
    (33)Very good
    0.3 miles from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 August 2017
    We LOVED our stay at the Andros Suite! The condo itself was clean and comfortable. The courtyard was breathtaking! The couple that are the property managers are PHENOMENAL...
    Reviewed 19 May 2016
    We loved our stay at the Andros Suite. The unit was very comfortable. They even had daily service who came in and cleaned and provided fresh towels (which was unexpected...
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    About this property
    Old Town Garden Villas - Andros Suite Book your well-deserved getaway to this dog-friendly Key West home. With a prime central location near Duval Street and access to a shared pool, this home will let up to four guests and your happy puppy (for a small nightly fee) unwind in style. Notice:...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    0.3 miles from Southernmost Point
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Terrace
    • Balcony
    • Grill
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home. This tropically inspired three level property has all the updated amenities for you and your guests to enjoy, plus be within walking distance of the Southernmost Point, the Hemingway...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Two-level dog-friendly cottage w/shared pool, outdoor shower - near the beach1 / 33
    (20)Very good
    0.3 miles from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 2015
    This is our second year at this location. This year we chose the Havana Suite. The unit was extremely clean and pleasantly decorated. Very nice kitchen. TVs in the bedroom and...
    Reviewed 27 April 2015
    We chose Little Havana initially because of the location. It is a smidgen off the beaten path from the hustle and bustle of the Duval action, yet within walking distance to a...
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    About this property
    Old Town Garden Villas - Little Havana Suite Slip into vacation mode at this dog-friendly Key West cottage. Featuring room for up to four people, two levels, a shared pool, and easy access to all of the seaside action, this home promises to make your next vacation fun-filled and hassle-free!...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    0.3 miles from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Duval Breeze1 / 24
    (57)Very good
    0.2 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 February 2020
    Location is great, very convenient. Unit was super clean. Rented for two weeks. On day six parking pass was lost,called AT HOME AT KEY WEST. At this time I was asked if they...
    Reviewed 6 July 2015
    First off At Home in Key West is awesome. We have used them twice and never had any trouble at all. They are very prompt, courteous and a delight to deal with. The condo...
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    About this property
    Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches! Enjoy the great location of this beautiful 2 bedroom 2.5 bath vacation home key west located in the gated rooftop community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.3 miles from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    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 19 September 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 4 June 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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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 4
    Romantic dog-friendly cottage w/shared pool, tropical decor, & easy beach access1 / 19
    (25)Excellent
    0.3 miles from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 October 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...
    Reviewed 19 August 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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    About this property
    Old Town Garden Villas - Caribbean Suite Book your romantic retreat to this dog-friendly Key West cottage. Enjoy the shared pool and a great location off of Duval Street. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am Located a few blocks from the Florida Keys...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    0.1 miles from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Air Conditioning
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    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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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 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 Garden
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information.I did not stay in this particular cottage but our guests had rave...
    Reviewed 7 October 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    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 7 April 2015
    Very well decorated an equipped with everything needed. Nice open area, the pictures do not do it justice. Larger living area and dining than the photos show. Two nice balconies...
    Reviewed 6 August 2014
    Excellently furnished, Immaculately clean. Completely up to date appliances and amenities. (Washer & dryer just off the kitchen!) Tip-Bring your own laundry...
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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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    0.3 miles from Southernmost Point
    Studio, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Truman * Duval - Unit B Enjoy this one bedroom apartment for your next getaway to Key West! Perfect for couples, this romantic spot is newly remodeled and will provide everything you need for a quick weekend escape! Beach towels are provided for your use. What's nearby: Located in the heart of...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 2 Bathrooms, Sleeps 4
    0.2 miles from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Patio
    • Wi-Fi
    • Private Garden
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Colada *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 charming home features a gorgeous, open floor plan, a heated, outdoor pool, beautiful landscaping, an adorable front porch for...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    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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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 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 Garden
    • 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
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Heart of Old Town getaway, perfect romantic retreat -near the action1 / 26
    (1)Excellent
    0.3 miles from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
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    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2019
    It's not big, but it's plenty for two people. The a/c unit was sufficient, the bed a little squeaky but comfortable, bathroom small but sufficient. Everything was clean and...
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    About this property
    Truman * Duval - Studio A Suprise your special someone with a stay at this charming and colorful Key West retreat! Set right in the heart of downtown, this home offers the perfect opportunity to enjoy a sun-kissed vacation you'll never forget. Located steps from the intersection of Truman Avenue...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Cozy, dog-friendly cottage w/ patio - walk to shops, restaurants, and more!1 / 25
    (29)Very good
    0.3 miles from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 May 2016
    Beautiful room, stocked kitchen, comfortable bed, private front porch. Loved everything about it! We only stayed one night but we could have stayed a month!
    Reviewed 13 July 2015
    Can't say enough about this place. Will never stay at another location in Key West. Staff was kind and helpful. Felt like this place was my own home, very cozy. Highly recommend.
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    About this property
    Truman Suite Enjoy the tropical ambience of this studio-style Key West cottage, where you'll find a private patio, dog-friendly accommodations, and a perfect location for dining, shopping, and exploring the local beaches and nightlife. This sweet yellow cottage is located in a small complex that...
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    Location Information
    Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
    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 11 December 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 25 October 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
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    0.3 miles from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view of the...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Sunny condo w/ shared pool & entertainment - central location!1 / 34
    (30)Very good
    0.4 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 December 2014
    Wonderful location, quiet. In desperate need of upgrades, 2 burner stovetop not fixed but portable one available, ac in bedroom starts and stops every 5 minutes...several...
    Reviewed 17 November 2014
    Nice,good location but no parking onsite 95% of time. Had to park 2 blocks away. Cooktop did not work so had to use portable 110 volt spare.
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    About this property
    Oceana Suite Take a remarkable retreat to Key West with this one-bedroom, one-bathroom cottage with a shared pool, and a great central location on the island! Sitting in a quiet location just off Truman Avenue and a few blocks down from Duval Street, you'll be within walking distance of any...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.2 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Parking
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A Tropical Paradise on the Atlantic Ocean in Key West, Florida, this one-bedroom, one-bathroom suite is located at the historic Coconut Beach Resort. Hidden from the street, on the quiet side of the island is the perfect blend of old island architecture, lush vegetation and walkways flowing onto...
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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 13 November 2019
    We enjoyed every thing about this house. Close enough to Duval. The pool was perfect size for 4 people.
    Reviewed 4 February 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.2 miles from Southernmost Point
    12 Bedrooms, 9 Bathrooms, Sleeps 36 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
    About this property
    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
    Holiday Rental House - 12 Bedrooms, 9 Bathrooms, Sleeps 36
    0.4 miles from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a complimentary weekly boat ride around Key West on a 33' Cruisers Yacht with your stay. A tropical and light beachy property right on Duval St. perfect for all the entertainment during Fantasy Fest. This location is centered on Duval St. so either direction there is happening entertainment...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.3 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Grill
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool. Key West Pinks, parties and drinks, that is the theme for this island retreat, Shrimp Party! When you think that a quick getaway to Key West is...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    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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    Amenities & Details
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2016
    Love the place! Location was good. There was an issue with ants in the kitchen. Also, I was issued 3 keys and 1 of the keys was not for our place. Changed the key with...
    Reviewed 21 April 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information.I did not stay in this particular cottage but our guests had rave...
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    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
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Leeward Isle Key West Retreat1 / 23
    (35)Very good
    0.3 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Terrace
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 January 2014
    We have rented in the Windward Park before, but this unit was the nicest unit by far. Recently updated and remodeled. Completely supplied with anything you will need.
    Reviewed 20 November 2013
    We just love this little get away home that we get to stay at when in Key West. The new owners have done a nice job of re-modeling and the Leeward Isle is so comfortable.
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    About this property
    Leeward Isle Key West Retreat – Location is everything! A hidden gem in the heart of Old Town Key West. Nestled in a quiet and private gated oasis of only 13 properties, this townhome community is located right in the heart of Old Town. It’s the perfect location to stay and explore Key West....
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    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 4 November 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 6 July 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
    Holiday Rental House - 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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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 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 3 April 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
    Spacious condo w/ balcony & shared pool - near shops & restaurants1 / 38
    (11)Very good
    0.2 miles from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Balcony
    • Terrace
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 February 2016
    This was at the southern end of Duval so not quite as noisy, which was nice. The restaurant below did play music in the morning which was annoying at times and the rooster would...
    Reviewed 14 March 2015
    The apartment was very comfortable and spacious. It is centrally located and although it's a little noisy at meal times, it is not a problem at night. It does need some minor...
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    About this property
    Casa Key West * Duval Square R32 Experience the beachy retreat you've been searching for at this dog-friendly Key West condo, where you'll enjoy a private balcony, a shared swimming pool, and a wonderful location for exploring. Beautifully positioned to overlook the gardens of Duval Square, this...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Island condo w/ balcony & great central location - beach nearby! Dogs OK!1 / 25
    (42)Very good
    0.1 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 November 2016
    Not even a block off Duval near the Southernmost end of the island (i.e., the quiet end of Duval), this efficiency was a great find. Located in a renovated old house with...
    Reviewed 10 November 2016
    The location is great. Right next to duval street. But it's definitely too small even for 4 persons.... we were walking in each other. One fan wasn't working and in the kitchen...
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    About this property
    Duval Corner This one-bedroom, one-bathroom condo in Key West, featuring entertainment, a wrap-around balcony, and beach access nearby! The family dog is also welcome to join you for an additional nightly fee. Located on the corner of Duval Street and Amelia Street, you'll be close to all the...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.1 miles from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • Private Garden
    • 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
    Tropical Dreaming1 / 24
    (59)Very good
    0.2 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 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...
    Reviewed 3 July 2017
    Nice and quiet with pool. Two bed rooms and two baths. Nice and clean house only draw back, has limited parking since we had 2 cars.
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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 pool, Tropical Dreaming is the classic example of the best of...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1.1 miles from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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
    About this property
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Historic, dog-friendly cottage in the heart of Key West w/ private hot tub1 / 36
    (16)Very good
    0.3 miles from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Washer
    • DVD Player
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 June 2016
    This house had a wonderful location. It was very easy to walk to Duval Street and the Southernmost Point. The beds were comfortable, but the house inside and out needs...
    Reviewed 1 July 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...
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    About this property
    Almost Southernmost If you're looking for a convenient home base for your Key West adventure, consider this two-bedroom, one-bathroom vacation rental. Up to six guests will enjoy the convenient location, a private hot tub, a fully equipped kitchen, and more! The family dog is also welcome to join...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    0.3 miles from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a complimentary boat ride weekly around Key West on a 33' Cruisers Yacht with your stay. A hidden Shangrila right on Duval St. perfect for your entertainment during Fantasy Fest. This location is centered on Duval St. so either direction there is some fun to be had during the day or night....
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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