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Holiday Rentals nearby Southernmost Point

Whitehead Street, Key West, Florida 33040
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    ₹ 16,332 Average
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    Travellers to Key West are booking December dates now. Secure your holiday home today, and have the perfect trip.
    All 100 Rentals in Key West
    Shelleys Rooftop Hideaway1 / 15
    (7)Excellent
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH1 / 122
    (7)Excellent
    0.2 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    PARKING,2bd/2bth,20yrd TO DUVAL,FREE OLD TOWN SHUTTLE,MAJOR ATTRACTIONS NEARBY1 / 41
    (2)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Dog-friendly home in a quiet neighborhood w/ shared pool & private hot tub!1 / 26
    (7)Very good
    0.3 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Grill
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Hot Tub
    • Parking
    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
    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. This home is nestled in a...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Dog-friendly home w/ private pool - walk to the beach and restaurants!1 / 27
    (2)Excellent
    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Terrace
    • Washer
    • Balcony
    • Parking
    • Internet Access
    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
    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 is mere blocks...
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    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Seaside Place Key West FL 5 Bedroom House 4 Baths1 / 64
    (40)Excellent
    0.1 kilometres from Southernmost Point
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • DVD Player
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This place has everything you could need and want while you stay in Key West. Conveniently located near restaurants, attractions and things to do. Very happy with Seaside Place!
    Reviewed 24 January 2017
    What a great house for our one-week getaway over the New Year holiday! We had a group of 11 people, and we were all comfortably housed inside the well-appointed home. From the...
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    About this property
    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer....
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    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Valhalla1 / 25
    (53)Excellent
    0.3 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 May 2018
    Beautiful villa. Peace and tranquility within easy reach of the heart of Key West. The most well-equpped kitchen I have found!
    Reviewed 13 December 2017
    Two blocks from the quiet end of Duval. Three blocks from the Southernmost Point. Ample on street parking and you can walk to Louie’s Backyard. Tim and his team at HH are first...
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    About this property
    This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Duval Balcony - Street Suite1 / 15
    (3)Very good
    0.6 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Housekeeping Included
    • Balcony
    • Cable/satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 January 2018
    Great location and great balcony overlooking Duvall St. This studio room was very clean and comfy. We will for sure stay again!!
    Reviewed 6 March 2017
    Tom was very nice and accommodating. He greeted us when we arrived. Great location in the heart of all the action of Duvall st and with this comes noise bring ear plugs for the...
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    About this property
    Located in the middle of Duval St, you are a 15 minute walk in one direction to the Atlantic Ocean and the Southernmost Point, and the same distance to the Gulf of Mexico and Mallory Square. Shopping, nightlife and the best restaurants are outside your front door. Hemingway House is 2 blocks away!...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    0.5 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Parking
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Quiet, dog-friendly getaway in a residential neighborhood with a shared pool1 / 25
    (4)Excellent
    0.3 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Cable/satellite TV
    • Internet Access
    • 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 cottage but our guests had rave reviews and I...
    Reviewed 5 March 2015
    My family and I stayed at Toon Hall the last week in February and had a blast. The home is located close to Higgs Beach, a few blocks away, and a few blocks from Duvall St. The...
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    About this property
    Grab your sunglasses, your beach towel, and charge your camera for a visit to this Key West home, once the winter home of Pulitzer Prize-winning cartoonist Jeff MacNelly. Offering a family-friendly atmosphere and a pristine shared pool, this home gives you the chance to experience the best of...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Caribbean Cottage ~ Duval Street Key West ~ Weekly Rental1 / 14
    (5)Very good
    0.3 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 August 2017
    Our group of 4 stayed here the first of August 2017. We thought the location was perfect with Duvall street, convenience stores and multiple bars & restaurants nearby. The...
    Reviewed 26 May 2017
    Best bed ever! Accommodations were everything listed and more. Easy check in and out. Floor plan gave us (2 couples) privacy. Pool was refreshing, even had a visit from a...
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    About this property
    Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Top Of Duval- 6 Bedroom Penthouse1 / 52
    (14)Excellent
    0.6 kilometres from Southernmost Point
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    This was such a perfect place for our group! All the suites are clean and large! The pool area was just perfect! You’re literally right in the middle of all the action of Duval...
    Reviewed 8 April 2018
    The location is perfect -- nearly equidistant from the Atlantic and the Gulf and in the midst of Duval Street restaurants, shops and bars. And, the rooms are great -- attractive...
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    About this property
    Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. It's like having your own private hotel. If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual...
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    Key West, Florida Keys
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    LOCATION! Feel like a Local! Spacious Suite steps off Duval St.-Eyebrow Suite1 / 24
    (4)Excellent
    0.5 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Patio
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2017
    This was our 2nd time staying with Andrews Inn and Cottages. They are amazing!! The staff is very accommodating, the suites are wonderful, and we can't wait to go back. I highly...
    Reviewed 23 March 2017
    Eyebrow House has a ton of room, lovely front porch and rear patio. The negative for senior citizens is that it has only a queen bed and hideabed which works for kids, not...
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    About this property
    The Eyebrow House is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local...
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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    LOCATION! Feel like a local! Treetop Studio w/ Jacuzzi steps off Duval St.1 / 7
    (3)Excellent
    0.6 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2017
    We booked the Treetop Studio for our first trip to Key West. Everything about it was perfect! The location is just a block off of Duval, but south of the crazy end, so the...
    Reviewed 28 March 2017
    What can I say? This was literally a perfect place from top to bottom. We stayed for a week and it was very nice to have a kitchen in room to save some $$. We loved going out to...
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    About this property
    The Treetop Studio is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Amelia Home1 / 24
    (55)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 April 2015
    What a great place to stay. Location is perfect. Everything you need is supplied. Decor and Landscaping were also wonderful. Already talking about next years stay. Nothing...
    Reviewed 2 April 2014
    Amelia Home was a great place to stay and experience Key West. The house is very clean and in excellent condition. The pool made the stay.The location is great. You can walk to...
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    About this property
    AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Amelia Home. This is the Key West Florida vacation home rental you have been seeking, tucked away in one of the...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Duval Street Suite1 / 22
    (44)Very good
    0.3 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 April 2018
    This townhome-type rental has a queen bed and a bathroom downstairs, and a king (with bathroom) in the loft. The downstairs sofa is a pullout bed, and an additional folding twin...
    Reviewed 18 February 2018
    We stayed in this condo mid January for two weeks. First let me thank Tim who was very helpful. The apartment was very clean, the beds are comfortable. The kitchen is well...
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    About this property
    It's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment. From your private and expansive...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Expansive group escape w/shared pool & five separate villas 1/2 block from Duval1 / 41
    (1)Excellent
    0.5 kilometres from Southernmost Point
    5 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    • Grill
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 February 2015
    I stayed here with a group of friends and we reserved all five of the villas for 14 people. Each villa had one bedroom and most had one and a half bath with a small kitchen that...
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    About this property
    This family-friendly Key West home features five separate villas grouped together, a shared pool, and a location that puts you close to all of the action. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am Located on Center Street, this home is just a mile from the Key West...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 20
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    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Washer
    • Balcony
    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 October 2016
    The management staff were very friendly. The house is right on Truman st. A couple of feet from Duval St. House as pictured in ad. We were a total of 8 people 5 adults and 3...
    Reviewed 25 July 2014
    This is our second time staying in this property. We stayed here again because the property manager & his team were fantastic, the property was very clean and it was a...
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    About this property
    Experience a quintessential Key West vacation when you stay at this historic three-bedroom, two-and-a-half-bathroom cottage. With a private heated pool, home comforts including free WiFi and cable TV, and room for up to eight guests, this home is perfect for a large family or a group of close...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.3 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Washer
    • Parking
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 January 2015
    Great location! 1/2 a block off the main street (Duval) and convenient to everything, but in a quiet dead end street. Private parking! (Hard to park anywhere in the Keys...
    Reviewed 12 January 2015
    Its just a few steps away from where all the actions is. Considering the location, it is actually quiet at night. We got ourselves lock out while drinking and partying at the...
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    About this property
    Spend your vacation days snorkeling in the clear coastal waters and strolling the streets of downtown Key West when you stay at this three-bedroom, two-bathroom cottage, which also features a private hot tub and one reserved off-street parking space. The family dog is also welcome to join you for...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.3 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    Reviewed 25 July 2014
    I can say this very simply, this is exactly what you picture in your mind when you think of a quaint bungalow in Key West, except more luxurious. Top notch value.
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    About this property
    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 renovated...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.6 kilometres from Southernmost Point
    4 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2014
    Tradewinds was the perfect place for 6 cousins to stay as we gathered in KW to send my sister's ashes off into her beloved warm ocean. The accommodations were perfect for the 6...
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    About this property
    Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a great location, each house features two bedrooms and one bathroom, a private parking space, dog-friendly accommodations, and a tranquil garden with a private hot tub in the back...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 12
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    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Internet Access
    • Washer
    • Parking
    • Grill
    • Air Conditioning
    • 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 26 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
    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 south end of the...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    0.2 kilometres from Southernmost Point
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Grill
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 December 2014
    The rental is great and in an excellent location. We had a group of 6 and had no issues. Note: unlike some rentals there is nothing in the house if you plan to cook. You...
    Reviewed 25 July 2014
    Everything was easy and perfect check in wise. Rooms were clean. Will stay here again. Walked to all bars and loved the tall ceilings.
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    About this property
    Immerse yourself in the island lifestyle when you book this Key West accommodation, comprised of a two-bedroom house and a separate one-bedroom pool house. Featuring a private heated pool, a private parking spot, and an outdoor shower, this home gives you the chance to unwind. Four dogs are...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.3 kilometres from Southernmost Point
    12 Bedrooms, 9 Bathrooms, Sleeps 36 Quick View
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    • Hot Tub
    • Patio
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2016
    We rented out the entire Tropical Village compound for our December 2015 destination wedding. While renting all 6 cottages may not be the "norm," it worked out perfect...
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    About this property
    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, hot tub, grilling...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 12 Bedrooms, 9 Bathrooms, Sleeps 36
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    0.3 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Patio
    • Air Conditioning
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    • Grill
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Slip into vacation mode as you explore Duval Street and dive into the beach scene when you book your trip to this dog-friendly Key West cottage. Featuring street parking, a relaxing shared pool, and a location that puts you right in the heart of the action, up to six guests and a canine companion...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Cable/satellite TV
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    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
    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 (for a small nightly fee). This...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.4 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Parking
    • Terrace
    • Air Conditioning
    • Balcony
    • Internet Access
    • Washer
    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
    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 condo offers guests unbeatable...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.5 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Patio
    • Grill
    • Cable/satellite TV
    • Washer
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This turn-of-the-century Key West vacation rental is ready and waiting to be your home away from home for your next family getaway. Spacious enough for up to eight guests and a dog (for a small nightly fee), this home comes with a tropically-landscaped back yard and a private, outdoor hot tub. This...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    0.3 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Washer
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    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
    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 dog is also welcome to...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.6 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Patio
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2016
    The location is awesome. The kitchen lay out is a train wreck! It was clean and daily towel and linen and linen service was good. Parking ....good luck. Overall it was a fair...
    Reviewed 5 June 2014
    Superb location, ideal for a few days in Key West. Only small but great outside space. Loads of character, only slight negative is the bathroom could do with a little tlc. But...
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    About this property
    Experience Key West in style with this dog-friendly vacation rental in the heart of Old Town! Up to six guests will enjoy a private hot tub and typical home comforts including a private washer/dryer, street parking, and free WiFi. Situated just one block from Duval Street, this cottage has no...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.5 kilometres 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
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    Casa Grande1 / 24
    (4)Excellent
    0.3 kilometres from Southernmost Point
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa Grande...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Poinciana House1 / 25
    (48)Excellent
    0.6 kilometres from Southernmost Point
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Grill
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2018
    My husband and I took our 13 year old daughter to the Poinciana House. Location is perfect for bikes: It was far enough from all the crazy noise of Duval street, but close...
    Reviewed 13 June 2017
    The house was a 1/2 block off Duvall Street. Was close to all restaurants and attractions. The house was very cute and clean. The pool was fantastic. We would definitely stay...
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    About this property
    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    0.6 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Air Conditioning
    • Internet Access
    • Balcony
    • Patio
    • Cable/satellite TV
    • Parking
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2016
    Close to where we want to be. Have booked this place twice in two years. And plan to rent again for our annual trip.
    Reviewed 15 May 2015
    I stayed here with four of my friends and the location was wonderful close to restaurants close to clubs and only a half a block off of Duval. this is a wonderful place and I...
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    About this property
    This cozy Key West rental comes with a shared pool (complete with a cascading waterfall), a furnished patio area, and space for up to six guests. It's perfect for that next family vacation or tropical getaway with a few friends. Please note that this home also comes with one private, off-street...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.5 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This two-bedroom, one-bathroom house is the perfect place for your next family vacation to the palm-tree paradise of Key West! With a great location downtown, a private parking space, and easy access to a sandy beach nearby, you'll be all set for fun in the sun. Located a half block from bustling...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.4 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Internet Access
    • Air Conditioning
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 May 2017
    Great adult week 1 block away from Duval street. the house was very clean! we had the best time ever!!!
    Reviewed 7 February 2015
    For $1700 for 5 nights, I expected a little more. First, I considered doing laundry on the last day, but the dryer door doesn't close (as evidenced by the tape marks all over it...
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    About this property
    Enjoy one of the most enviable locations in Key West when you escape to this two-bedroom condo, where you'll have a dog-friendly interior, a private covered porch, and wonderful access to beaches, restaurants, and the Old Town. This gated property sits in the heart of Old Town Key West, just one...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Tropical Dreaming1 / 24
    (58)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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.
    Reviewed 22 July 2015
    Very Nice! Photos are true to form. Needed a place we could bring our small dog. Perfect distance from Duval. Pool was small but we had only 4-6 max (plus the dog). Grilled a...
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    About this property
    TROPICAL DREAMING -- A distinctive private Key West vacation home with sparkling pool, Tropical Dreaming is the classic example of the best of both worlds while vacationing in Old Town. Only a short stroll over to Duval Street, where entertainment and activity abounds or 4 blocks to the Atlantic...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.3 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Internet Access
    • Parking
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The sunny paradise of Key West beckons, and this dog-friendly home is the perfect place to stay, with a private patio and hot tub 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 Key West, from...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Duval Square1 / 22
    (47)Very good
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 March 2018
    Super location on Duval Street no far from the Southernmost Point and within walking distance to great restaurants and entertainment. This condo has everything you need for an...
    Reviewed 16 January 2018
    Absolutely beautiful, we so enjoyed this location and the condo itself. Safe, Secure, Parking, Bike racks inside the garage Clean, well stocked, beautifully...
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    About this property
    There's no more perfect place to practice the art of tropical vacationing than this professionally decorated, two-story townhome, which features two bedrooms, two and a half baths, a private deck with private hot tub, and a master bedroom balcony. A short walkway flanked by lush gardens leads to a...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Stunning home near beach and town with private hot tub and shared pool - dogs OK1 / 24
    (5)Very good
    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
    • Grill
    • Parking
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 March 2014
    We were at Tobago House for the month of February 2014. It is absolutely wonderful !! I will say that I would have preferred if everything had been tested out before we got...
    Reviewed 23 January 2014
    Tobago House is very nice, close to Duval - quiet street.Nice amenities, pool, hot tub, great outdoor area. Would recommend to anyone. Close walk to everything.Wonderful!
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    About this property
    Make your next stay in the Florida Keys one to remember with this amazing home in Key West! Three bedrooms, three bathrooms, dog-friendly accommodations, and a shared pool ensure your next trip to the tropics will be one you'll always remember. Your home is only a block away from the famous shops...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    0.5 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Hot Tub
    • Internet Access
    • Parking
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Washer
    • DVD Player
    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
    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 you for an additional...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.0 kilometres from Southernmost Point
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Parking
    • Air Conditioning
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This four-bedroom Key West home has just what you need for an awe-inspiring Florida beach getaway, including a private heated pool, rooftop patio with a fantastic ocean view, and easy access to the beach and major attractions. You'll be a few steps from Southernmost Point, and you can walk to Key...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    0.2 kilometres from Southernmost Point
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Parking
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in style in the heart of Key West's historic downtown, where you're steps from the beach and all Duval Street has to offer! Your back patio houses a private hot tub, dog-friendly accommodations, and grill, perfect for lounging with the group after a long day of play. You're located on...
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    Location Information
    Stock Island, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    0.4 kilometres 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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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    0.3 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Cable/satellite TV
    • Washer
    • Balcony
    • Parking
    • Terrace
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Head to Key West and revel in access to a shared pool, dog-friendly accommodations, and close proximity to beautiful beaches and major attractions when you stay at this three-bedroom, three-bath home for six. Dogs are also welcome for a small nightly fee. This rental is located in the heart of Old...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    0.7 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 September 2015
    I just returned from a long weekend in beautiful Key West and the Verde Suite was a perfect choice. It was clean, comfortable and just far enough away from the hustle of the...
    Reviewed 30 June 2015
    We really enjoyed our few days here and thank goodness for the refreshing pool because it was HOT HOT HOT! We enjoyed meeting a couple of other folks in the quaint cluster of...
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    About this property
    There's nothing like a tropical atmosphere to reset and this colorful one-bedroom, one-bathroom cottage in Key West is the place for you. Featuring access to a shared pool, entertainment, and a full kitchen, you'll have everything you need for a vacation in paradise. The family dog is also welcome...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    0.3 kilometres from Southernmost Point
    5 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Patio
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West home for nine offers privacy right in the heart of all the action with amenities like a private hot tub and close proximity to the island's most notable attractions. You'll feel a sense of seclusion in this home, thanks to its location behind a charming gate and surrounded by lush...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 9
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    0.6 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Parking
    • Patio
    • Internet Access
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 December 2015
    We stayed in this property for two days. We had a good time. Staff is friendly. They have everything what we need there. I read reviews about this property and some one...
    Reviewed 12 December 2015
    Nice location. Hot tub, patio nice, porch fun to watch traffic a passerbys with morning coffee. Houe is cute but needs a little TLC. Fingerprints on walls and doors, missing...
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    About this property
    Bask in the peaceful sunshine of Key West and feel all your stress melt away when you stay at this cozy dog-friendly cottage right in town. With a private hot tub in the garden area out back plus all the conveniences of home, what's not to love? Sitting only half a block from all the fun and...
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    Location Information
    Sugarloaf Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    0.5 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Historic Preservation Award Winner! This licensed vacation home was recently featured on Key West's historic home tour and is available to rent monthly. We recently completed a massive 6-month remodel, making this one of the more spectacular vacation homes you'll find for rent in Old Town. In...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Vintage Luxury Cottage ~ Weekly Rental1 / 11
    (6)Very good
    0.3 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 April 2018
    Loved the cottage. Loved the location. Very quiet even though it’s steps from Duval. The only reason I don’t give it five stars were little details such as the shower drain was...
    Reviewed 4 January 2018
    Read the comments about shade around pool. True, but we thought it was a wonderful place, When at the beach most of our time is under an umbrella, Immaculate and nicely...
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    About this property
    Without a doubt, one of the rarest private Key West vacation cottages available. Situated in one of the most requested locations in Old Town Key West, this luxury renovated turn-of-the-century Vintage Luxury Cottage vacation rental is hidden just off upper Duval Street in Old Town. Enter the gate...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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