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Stock Island Holiday Homes

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    Stock Island is popular with travellers just like you. Don’t let them get your perfect place first—book today!
    All 254 Rentals in Stock Island
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    Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!1 / 25
    (18)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Key West home w/shared pool and just steps from historic Old Town1 / 29
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Newly remodeled family home with a shared swimming pool and fitness center!1 / 39
    (3)Average
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Dog-friendly, tropical escape with central location, hot tub, and shared pool1 / 25
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Wi-Fi
    • Patio
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 December 2016
    My boyfriend and I stayed here for 4 nights in October. The house was very clean and the check in process was very easy. The house has a small shared pool with the other condos...
    Reviewed 1 August 2014
    The Flamingo Hideaway is a ground floor unit in a small condo complex of renovated, period buildings. This unit is tucked away from the street and right next to the shared pool...
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    About this property
    Flamingo Hideaway Surround yourself with peace, tranquility, and seaside fun when you book your trip to this Key West cottage. Enjoy the bubbling hot tub, shared pool, and easy beach access. Nestled in the Palm Gardens condo community in Old Town Key West, this tropical home embraces you with...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Comfortable condo w/ shared pool, private balcony, and beach access1 / 27
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 January 2015
    This was not as I expected. The place is very clean. Here are my things that I as not expecting. U can not go right to the beach in front of this place all rocks. Smothers beach...
    Reviewed 17 November 2014
    The condo was a very nice rental on the south side of Key West. The decor was modern and the condo had a classy feel. The large balcony patio was wonderful to sit out on in the...
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    About this property
    Atlantic Ocean View Escape to Key West's beaches during a stay at Atlantic Ocean View, where you'll enjoy prime island location and access to a shared pool. This condo accommodates up to six, so it's a great choice for the whole family! The condo backs up to a stretch of Higgs Beach, so you're...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Recently renovated home w/ shared pool, furnished patio area - in town, dogs ok1 / 28
    (2)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 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 8 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 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Keepin' it Reel *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. Enjoy the privacy that this waterfront condo has to offer during your next vacation to Key West. This condo is perfectly situated off...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Family friendly condo w/ shared pool, hot tub & dogs ok!1 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Terrace
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Saint Lucia Suite 201 Escape to the sunshine and soft sands of the Florida Keys with this amazing dog-friendly home in Sunrise Suites Resort in Key West with a shared pool. Enjoy bird watching at the Salt Ponds Preserve from the comfort of your private balcony. Back at...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Cozumel Suite 112 Wake up every morning to the crisp smell of the ocean when you stay at this cute condo on the shores of Key West! Complete with upscale resort amenities like a shared pool and hot tub, tennis courts, and a private, covered parking space, this comfortable rental is...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Washer
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Tahiti Suite 104 Caribbean comforts await at this lovely Key West condo just five miles from the island's historic downtown. With amenities like a private pool and hot tub, tennis courts, a private balcony, and a covered parking spot, this comfortable condo is perfect for anyone...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunset Marina Retreat *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 waterfront condo, located within a gated community, boasts incredible views of the water and spectacular sunsets. With a...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Dog-friendly home w/ private pool - walk to the beach and restaurants!1 / 26
    (2)Excellent
    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
    Reviewed 1 March 2018
    Had a great surprise birthday weekend in Key West. The house was fantastic! Very clean and bigger than the pictures make it seem. Loved the heated pool, and close walk to Duval...
    Reviewed 23 January 2017
    3 levels of beautifully decorated accommodations! Walking distance to famous Duval St, bars, restaurants and shopping. Loved it!
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    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 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Washer
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Samana Cay Suite 405 Immerse yourself in the laid-back ambiance of the Florida Keys with a stay at this colorful Key West condo! Complete with a shared pool and hot tub, tennis courts, dog-friendly policies, and a reserved parking spot, this comfortable vacation rental will have...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Hot Tub
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dreaming of a quiet tropical vacation surrounded by palm trees? Our residence is the place for you! Offering a relaxing location away from the hustle and bustle, but close enough to partake in all the activities that Key West has to offer, our guests will enjoy access to three outdoor pools, daily...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Hot Tub
    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dreaming of a quiet tropical vacation in a luxurious town home with an equipped kitchen? Our residence is the place for you! Offering a relaxing location away from the hustle and bustle, our guests will enjoy access to three outdoor pools, daily breakfast, housekeeping, air conditioning, and more...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Terrace
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your holiday amid luxury when you stay in our suite that has a spiral staircase, a large private courtyard, original artwork, and air conditioning. Offering a relaxing location away from the hustle and bustle, our guests will enjoy access to three outdoor pools, daily breakfast, housekeeping,...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Lovely dog-friendly home w/ mother-in-law cottage - great location, private pool1 / 29
    (5)Very good
    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 2 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 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • Hot Tub
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Dreaming of lazing in a hammock surrounded by palm trees? Our residence is the place for you! Offering a relaxing location away from the hustle and bustle, our guests will enjoy access to three outdoor pools, daily breakfast, housekeeping, air conditioning, and more when they stay here. • 2 Queen...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Beautiful condo with a deck/patio & shared pool - walk to beaches, Duval & more!1 / 26
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 November 2015
    We visited the Annex for Fantasy Fest a few years back. The location is perfect! Close enough to the action of the main streets, but private enough for some peace when you're...
    Reviewed 20 January 2015
    Great location; we loved having the back gate for direct access out to Angela Street and the close proximity to the Green Parrot and Blue Heaven - two of our Key West favorites...
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    About this property
    Secret Garden Find the best of Key West at your doorstep with this beautiful two-bedroom condo, a lovely South Florida escape with a private deck and patio, a shared swimming pool, and a wonderful location close to restaurants, beaches, and more! Perfectly located between Truman Annex and Bahama...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    • Hot Tub
    • Washer
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Commodore's Compound Spend your Key West vacation in style here at this high-end house with a private hot tub! There's plenty of room for everybody in this house's eight bedrooms, and you're steps away from the ocean. Key West's most popular attractions surround this home - walk down to Mallory...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    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 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Sunny condo w/ entertainment, balcony, & great location near the beach! Dogs OK!1 / 26
    (1)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Terrace
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Frontier Flat Escape to the land of sea and sun for your next vacation with this fresh condo in Key West. Featuring one bedroom and one bathroom, entertainment, and an awesome location close to all the action on the waterfront, up to four guests will love it here! The family dog is also...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Contemporary beachside escape with shared pool and close to local attractions1 / 25
    (4)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2014
    We had a wonderful time staying in Key West. The condo location was perfect. We walked everywhere. The beds were comfortable, and although the kitchen is very small, it was...
    Reviewed 13 March 2014
    This place is a very nice place to stay.Key West Vacation Rentals are very helpful and easy to reach.The location is perfect just 5 minutes walk to Duval Street and 15 min to...
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    About this property
    Lazy Lane at Shipyard Condos Grab your sunglasses, bathing suit, and sunscreen and get ready to dive into the beach lifestyle when you book this Key West condo. Boasting a shared pool to stay cool, this home gives you the chance to slip into vacation mode with ease. This condo is just two...
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    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Dog-friendly home in a quiet neighborhood w/ shared pool & private hot tub!1 / 26
    (7)Very good
    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 22 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 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Welcoming Sunrise Suites condo w/ balcony views, pool/hot tub- dog-friendly1 / 28
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2019
    When in Key West, I like to stay in a place that is quiet, comfortable and has easy assess to get around the island. This place has all of that. Even a bus line outside the...
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    About this property
    Sunrise Suites - Bimini Suite 211 This two-bedroom, two-bathroom suite allows you to show your friends and family the Florida getaway they deserve! Whether you want to explore the beaches or simply relax by the pool, all of Key West's wonders are out there waiting for you. When you've toweled...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Couple's dog-friendly getaway with central location and access to a shared pool1 / 26
    (39)Very good
    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 5 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 1 March 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 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Washer
    • Terrace
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Rum Cay Suite 304 Come to Key West and unwind with this comfortable and inviting two-bedroom condo! A shared pool and a private balcony with scenic views of the marsh add to the feeling of relaxation. The family dog is also welcome to join you for an additional nightly fee. This...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Terrace
    • Balcony
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Tierra Bomba Suite 403 Relax under azure skies and the gently rustling fronds of palm trees when you stay at this elegant and dog-friendly Key West condo! A community pool and hot tub, tennis courts, a parking space, and pool views from your private balcony add to an atmosphere of...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Contemporary dog-friendly cottage with easy beach access and shared pool1 / 31
    (33)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Shared Outdoor Pool (Unheated)
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    • 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 20 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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    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 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    Dog-friendly condo w/ shared pool and hot tub with free parking!1 / 33
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Terrace
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    • Hot Tub
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 May 2019
    This is a lovely place to spend a few days and our little dog did well here. The apartment is decorated cute and functional with a king bed and queen bed in separate bedrooms...
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    Sunrise Suites - Saint Martin Suite 207 Your loved ones deserve to rest and relax under some Florida sunshine. Give them the vacation they deserve with this dog-friendly Key West condo with shared amenities like a pool and a hot tub. A private parking spot is provided for your convenience....
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Historic house w/ private pool & easy beach access - ideal for groups! Dogs OK!1 / 31
    (1)Very good
    7 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Grill
    • Patio
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 May 2016
    We stayed in one of the units at the property (Banana Split). This is a 1 bedroom / 1 bath apartment on the second floor. It has a full kitchen, small sitting area and two decks...
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    Banana's Foster Guesthouse Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large historic house on Key West. Featuring a private heated pool, four private parking spaces, and a communal area with plenty of room for everyone, this seven-bedroom,...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 18
    Family friendly condo w/tennis, shared pool, hot tub, & private balcony- dogs ok1 / 24
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Hot Tub
    • Balcony
    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2016
    The location is nice because it's quiet. The unit and kitchen supplies need updating. The view from the balcony is nice. The pool area is nice.
    Reviewed 15 March 2016
    This 2 bedroom condo in Key West was really great. The staff went out of their way to make us feel welcome. They checked to see if our room was ready and clean early and it...
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    Sunrise Suites - Margarita Suite 305 Leave your troubles behind and head for the beach with this delightful and dog-friendly Key West condo! Incredible amenities like a shared pool and hot tub, tennis courts, and a private balcony with views of the marsh ensure you'll have a vacation to remember....
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Two-level dog-friendly cottage w/shared pool, outdoor shower - near the beach1 / 33
    (20)Very good
    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 28 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 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Flagler's Crossing *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.* Explore the tropical surroundings of Key West in style from the comfort of this dog-friendly condo! A shared pool, ocean views,...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Conch Cottage *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. Enjoy this classic Key West cottage featuring a shared pool and a furnished patio, located within blocks of beaches, shops,...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Heart of Old Town getaway, perfect romantic retreat -near the action1 / 26
    (1)Excellent
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
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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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    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 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Curry House Room 5 Experience a piece of Key West's past when you book a stay at this charming ground-floor suite in the historic Curry House Bed & Breakfast! Up to two guests will enjoy a shared on-site pool, home comforts, and a convenient location in the heart of the city. Curry House sits...
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    Location Information
    Stock Island, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Balcony
    • Washer
    • Terrace
    • Hot Tub
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Big Kahuna Suite 202 Spend your next Key West vacation at this lovely condo in the Florida Keys. This rental comes equipped with a shared pool, hot tub, and tennis courts, along with central air-conditioning, a private balcony, and a fitness room. What's Nearby: This condo...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Deluxe, ground-floor studio w/ view of the courtyard and pool - close to shops1 / 26
    (14)Very good
    Studio, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Washer
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    • Patio
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 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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    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 33040
    Condo/Apartment - 1 Bathroom, Sleeps 4
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Shipyard Hideaway Bask in the tropical warmth of Key West at this two-bedroom condo, where you'll enjoy a beautiful community swimming pool, a private patio dining area, and an outstanding location close to beaches, shops, and restaurants. This condo is located in the lovely Truman Annex...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Dog-friendly condo w/ private hot tub & shared pool - close to shops & beaches1 / 25
    (16)Very good
    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 13 April 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 11 December 2014
    Amazing condo ! Great Staff ! Beautiful place with comfy beds and all the comforts of home and then some ! Hot Tub !!! Full kitchen w/washer and dryer. Gated parking and 2 pools...
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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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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Colorful condo w/ deck, balcony & shared pool - near downtown & beaches1 / 26
    (23)Very good
    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 8 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 7 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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    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 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunrise Suites - Catalina Suite 311 Escape to the sunny shores of Key West with a stay at this comfortable two-bedroom condo. Complete with a shared pool, an on-site parking space, and a private deck for taking in the views, this dog-friendly vacation rental has everything you need for an...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Cable/satellite TV
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    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Seaport Suite Situated on the second floor of a historic home, this spacious dog-friendly condo welcomes guests with great amenities and a private hot tub! Soak after a long day in the sunshine, and make full use of the back patio space. You're right around the corner from Duval Street's...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Banana Breeze * Key Cove #4 *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. Escape to Key West and stay in this lovely waterfront home for a luxurious getaway. Your group will enjoy a private pool,...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Frontier Suite *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. Get away from it all and head to Key West for a sun-filled vacation with this two-bedroom, two-bath condo for six and enjoy easy...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Contemporary seaside cottage w/ private hot tub, shared pool - dogs welcome!1 / 24
    (29)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2015
    My wife and I recently rented this unit for the first week of February. Overall, I’d call it a solid good! We liked the location, with a grocery store and an excellent...
    Reviewed 3 September 2014
    I stayed here this past Labor Day weekend for a friend's bachelorette party. There were 10 of us, and the Heron Hideaway as well as the three other one-bedroom condos in the...
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    Heron Hideaway Surrounded by possibilities for fun and relaxation, this Key West cottage offers up to four guests the chance to bask in the warm Florida sun. Featuring a private hot tub, pristine seasonally heated shared pool, and easy access to a wide range of local attractions, this home puts you...
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    Location Information
    Stock Island, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Romantic dog-friendly cottage w/shared pool, tropical decor, & easy beach access1 / 19
    (25)Excellent
    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 9 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 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
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    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Atlantic Parrot This beachfront condo in Key West offers a much-needed pop of color to your Florida Keys vacation! You'll enjoy views of the ocean from your private balcony, as well as an open floor plan that provides ample space for everyone to relax. This complex features wonderful shared...
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    Location Information
    Stock Island, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Penthouse w/ private hot tub & shared pool - close to beaches, dogs OK.1 / 35
    (28)Very good
    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 13 March 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 17 September 2015
    Very nice place in a great location. Close to everything and very convenient. Staff was excellent, place was clean and service by the concierge was top notch. I would stay...
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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 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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