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Holiday Rentals near Southernmost Point

Whitehead Street, Key West, Florida 33040
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 50 Rentals in Key West
    Key West Townhouse in stunning 5 Star Resort * Close to Duval Street and beach1 / 19
    (1)Excellent
    0.2 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    LA DOLCE VITA, OLD TOWN KEY WEST!! STEPS TO DUVAL!!  SLEEPS 2-4, 3 BLKS TO BEACH1 / 61
    (9)Excellent
    0.2 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Conch Haven Old Town 1/1 MONTHLY Rental1 / 16
    (5)Very good
    0.5 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Seaside Place Key West FL 5 Bedroom House 4 Baths1 / 57
    (42)Excellent
    0.1 kilometres from Southernmost Point
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 February 2021
    We are 2 families who travel together frequently. Covid helped screw a couple trips up so we were determined to make this trip work. We met in Homestead to allow the kids to...
    Reviewed 15 November 2019
    I stayed here with a group of 10 friends. 4 couples and three singles. We had the best time. The house is beautiful. The pool amazing. Abby was responsive and helpful. Our...
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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
    0.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view of the...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1.8 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    • Sauna
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval1 / 24
    (111)Excellent
    0.2 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Luxury 2/2 condo In Heart Of Key West With Lagoon Pool. Monthly rentals only1 / 23
    (4)Excellent
    0.9 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    'TORTOISE SHELL II' ~ Comfortable, Modern Condo Two Blocks from Duval!1 / 15
    (7)Excellent
    1.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Attitude Key West (2 Bikes and Wireless Internet)1 / 50
    (108)Excellent
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 2
    Craig & Cindy Key West Truman Annex Shipyard Condo with a deck at Mile Marker 0!1 / 50
    (10)Excellent
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Reviewed 26 April 2021
    We stayed at Shipyard 206-7 by Cindy & Craig in October 2020 for 7 nights. The location is prime; not too far from Duval and all the fun activities, but def far enough away...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Truman Annex, two blocks from Duval1 / 27
    (57)Very good
    1.3 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    'LOST SHAKER OF SALT' ~ 3 Bed, 2 Bath Pet Friendly Home with 40' Private Pool1 / 14
    (103)Excellent
    1.0 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Craig & Cindy Key West Truman Annex 212 Fleming House1 / 47
    (18)Excellent
    1.1 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Craig & Cindy Key West 3 Bedroom Waterfront Beachside Resort Condo1 / 50
    (45)Excellent
    4.3 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    The Tree House Old Town 2 Bedroom MONTHLY Rental1 / 17
    (7)Very good
    0.5 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Grill
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    • Porch
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    Pet friendly
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    Reviewed 2 November 2018
    I booked this property for a 28 day stay and I'm so glad I did! What a great location! An easy 4 minute walk to Duval St and a 3 minute walk to the spectacular MLK Community...
    Reviewed 5 August 2018
    one of the best places and time i have in Key West.Super house,total privacy,very quiet naibourghood.coming back next year
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    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
    Key West Golf Club - Completely Renovated - Tree House Too.1 / 21
    (11)Excellent
    6.7 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    'SOUTHERNMOST BELLE'~ Heated Pool, Gourmet Kitchen & Elegant Large Bedrooms!1 / 41
    (82)Very good
    1.4 kilometres from Southernmost Point
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    Reviewed 6 March 2021
    This is a lovely property. The front yard was such a nice oasis for privacy & relaxation. There were only four of us and we had plenty of indoor space as well. The...
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    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Majestic Escape near Duval!  Pool, wifi, renovated 2/2 1/2, private courtyard.1 / 50
    (61)Excellent
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    'THE QUARTERDECK' ~ Colorful & Comfortable 2Ba/ 1Ba Unit in The Shipyard!1 / 10
    (44)Very good
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    'TIDES ON SIMONTON' ~ Perfectly located just off Duval and all the fun!1 / 18
    (95)Very good
    0.7 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    'CASA DE VINO' ~ Excellent Price for an Amazing Townhouse with Pool & Tiki!1 / 24
    (59)Excellent
    6.6 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Tom's Chicken Coop:  Nice Ocean View, Pool, Renovated, Close to Beach1 / 40
    (78)Excellent
    1.9 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    'CORAL CABANA' ~ Lush Porch Views of the Pool & Gardens, near Golf Course!1 / 19
    (81)Excellent
    6.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Tropical Key West Get Away1 / 33
    (92)Very good
    6.5 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Great location! Everything one would need. 3 month minimum1 / 13
    (5)Excellent
    0.7 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Secret Villa I * Old Town with Private Pool, close to Duval!1 / 24
    (65)Excellent
    1.1 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    BEST DEAL IN THE KEYS!1 / 26
    (99)Very good
    1.1 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Secret Villa II * Old Town: Beautiful Home w/ Private Pool, 2 blocks to Duval!1 / 24
    (42)Excellent
    1.1 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    'OFF CALL' ~ Rustic, Nautical Decor With King Master Suite & Heated Pool!1 / 21
    (62)Very good
    6.4 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Harbour Place 115 in Truman Annex Key West1 / 23
    (63)Excellent
    1.1 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi1 / 50
    (195)Excellent
    1.0 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.5 kilometres from Southernmost Point
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    A beautiful three-story home with private pool, off street parking, and attractive decor, Ecco Domani is a wonderful Key West escape that you will want to come home to year after year. Beautifully designed and decorated this private home has a gourmet kitchen with French doors that lead to a...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.5 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
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    About this property
    Gated compound walking distance to Duval Street but behind the gates quiet solitude in your beautiful home with front porch overlooking the sparking pool. Key West Pinks, parties and drinks, that is the theme for this island retreat, Shrimp Party! When you think that a quick getaway to Key West...
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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Key West Gem - Large, Bright 2 BR Condo on Ocean w/ Olympic-size Pool1 / 31
    (126)Excellent
    1.9 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Sauna
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Terrace
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    • Shared Outdoor Pool (Unheated)
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    About this property
    Location! Location! Location! Duval Breeze offers the best location in town! Walking distance to restaurants, bars and galleries and easy biking distance to the beaches! Enjoy the great location of this beautiful 2 bedroom 2.5 bath vacation home in Key West located in the gated rooftop community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Do not look any further! Your perfect vacation home rental is right here! Offering a private pool with lounge chairs and covered outside porch. You can also bring your Fido! A distinctive private Key West vacation home with sparkling private pool, Tropical Dreaming is the classic example of the...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.3 kilometres from Southernmost Point
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
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    About this property
    Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions! CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    After a long day cool off in your private pool, enjoy cold Mojitos on the covered porch and cook up some fresh grouper on the grill! Welcome to your dream vacation home! The Amelia home is a 2 bedroom 2.5 bath retreat with sparkling private pool that is only four blocks from the Atlantic Ocean and...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.5 kilometres from Southernmost Point
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Amid the most iconic historic sites in Key West you’ll find the Lighthouse Villa, a timeless and private Conch home. This tropically inspired three level property has all the updated amenities for you and your guests to enjoy, plus be within walking distance of the Southernmost Point, the Hemingway...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    0.4 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located above a courtyard “mall” with shops and restaurants on upper Duval Street - you’ll find the delightful Duval Sea Turtle town home within easy walking distance to everything! Meticulously decorated with art from local galleries and artists, you’ll be greeted by the super-sized sea turtle...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Conch Get Enough!  - Key West's Old Town Truman Annex1 / 32
    (140)Excellent
    1.1 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    Pet friendly
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    Sunshine Daydream: Private Home 1/2 Block Off Duval in Gallery District -1 / 22
    (112)Excellent
    0.2 kilometres from Southernmost Point
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    0.5 kilometres from Southernmost Point
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
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    • Private Garden
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    Pet friendly
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    About this property
    THE PROPERTY: Eleanor's Place has everything you might want on your monthly vacation to Key West, beginning with your own private parking space (a rarity in Old Town) and cozy front porch. Eleanor's Place is located in historic Old Town Key West in Bahama Village. This charming house has...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Truman Annex: The Plantation SELF CATERING  beautifully landscaped rear patio1 / 17
    (70)Excellent
    1.1 kilometres from Southernmost Point
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    0.2 kilometres from Southernmost Point
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
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    • Grill
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    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy Island life and live like a local in this perfect cottage on a quiet street in Key West. A welcoming outdoor space with a relaxing feel, this rental features a private hot tub and grill for outdoor entertaining. The rear entry to this quaint cottage has French doors that open to rich...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
    Truman Annex Best Location in Town1 / 31
    (27)Excellent
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
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    • Washer
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Sunset and Ocean View in Key West's Truman Annex with 2 Bikes and Pool Access1 / 51
    (185)Excellent
    1.0 kilometres from Southernmost Point
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Washer
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    • Cable/satellite TV
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Superb Location, Affordably Priced1 / 50
    (155)Excellent
    0.9 kilometres from Southernmost Point
    Studio, 1 Bathroom, Sleeps 1 Quick View
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 1
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