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Holiday Rentals near Sunset Pier

Duval St, Ocean Key Resort & Spa, 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 49 Rentals in Key West
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    0.4 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    0.3 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    0.4 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    A spacious, airy 3-bedroom, 3-bathroom penthouse at The Galleon Resort & Marina in the Old Historic Seaport in Key West. Available from Saturday March 31 to April 7, 2018. Weekly Rental Only. The first level of the penthouse has a full kitchen and wet bar, with a washing machine and dryer. There...
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    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    0.3 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.3 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Best location in Old Town, Steps to Duval St and Mallory Square. Rare private beach and fishing pier. Tiki Hut, Pool and spa, Observation decks. On boardwalk to all casual and more upscale spots. All units renovated with beautiful appointments. One parking spot for stay. Full kitcvhen, large...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Harbor Walk Hideaways1 / 22
    (22)Excellent
    0.4 kilometres from Sunset Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    Reviewed 30 April 2021
    As pictured, nothing fancy, was clean, perfect for a big group and is a great location! Gail was very responsive and helpful. It did take the owner awhile to respond sometimes...
    Reviewed 7 September 2019
    We loved our stay! We have been trying to find time to visit again. You open the gate from the busy street and it’s literally like you walk into another world. The plants and...
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    About this property
    Very private gated compound sleeping eight guests right in the heart of Key West's Old Town. Enjoy the beat of Key West's nightlife, the romance of sunset at Mallory Square, or the excitement of deep sea fishing or water sports all less than a two-minute walk from our tropical paradise. Standing...
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    Key West, Florida Keys
    Private Room - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    'LADY ADMIRAL' ~ Sweet cottage & guest house with private pool off Duval1 / 24
    (107)Excellent
    1.7 kilometres from Sunset Pier
    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
    1.0 kilometres from Sunset Pier
    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
    0.5 kilometres from Sunset Pier
    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
    (107)Excellent
    0.9 kilometres from Sunset Pier
    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
    (9)Excellent
    0.9 kilometres from Sunset Pier
    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
    (54)Very good
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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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
    (99)Excellent
    0.8 kilometres from Sunset Pier
    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
    (17)Excellent
    0.7 kilometres from Sunset Pier
    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
    (41)Excellent
    4.6 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Key West Golf Club - Completely Renovated - Tree House Too.1 / 21
    (11)Excellent
    7.1 kilometres from Sunset Pier
    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
    (79)Very good
    0.5 kilometres from Sunset Pier
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
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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
    0.9 kilometres from Sunset Pier
    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
    'THE QUARTERDECK' ~ Colorful & Comfortable 2Ba/ 1Ba Unit in The Shipyard!1 / 10
    (42)Very good
    0.9 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    'TIDES ON SIMONTON' ~ Perfectly located just off Duval and all the fun!1 / 18
    (89)Very good
    1.1 kilometres from Sunset Pier
    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
    7.1 kilometres from Sunset Pier
    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
    3.2 kilometres from Sunset Pier
    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
    7.1 kilometres from Sunset Pier
    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
    7.0 kilometres from Sunset Pier
    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
    1.6 kilometres from Sunset Pier
    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
    (60)Excellent
    0.8 kilometres from Sunset Pier
    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
    (92)Very good
    0.8 kilometres from Sunset Pier
    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
    0.8 kilometres from Sunset Pier
    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
    7.0 kilometres from Sunset Pier
    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
    (62)Excellent
    0.7 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    0.5 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    About this property
    View passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building! Balmy breezes, brilliant sunrises, and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex. You'll spend most of your time overlooking...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi1 / 50
    (192)Excellent
    1.0 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    0.3 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Charming 1 bedroom apartment with comfortable King size bed (100% cotton sheets) in the best possible location. The heart of Old Town Key West, two blocks from Simonton beach, the seaport, watersports and four blocks from Mallory Square. Walk everywhere, to the Historic Seaport, Hemingway House,...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.3 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    Charming 1 bedroom apartment with comfortable King size bed (100% cotton sheets) in the best possible location. The heart of Old Town Key West, two blocks from Simonton beach, the seaport, watersports and four blocks from Mallory Square. Walk everywhere, to the Historic Seaport, Hemingway House,...
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    Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    0.7 kilometres from Sunset Pier
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    Pet friendly
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    About this property
    Twice the comfort, twice the amenities, that’s The Dolphin House, located in the exclusive Truman Annex community in the heart of Old Town. Wonderful for larger groups or family get-togethers, The Dolphin House offers a roomy vacation home and quaint guest house with a pool and outdoor living...
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    Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Key West Gem - Large, Bright 2 BR Condo on Ocean w/ Olympic-size Pool1 / 31
    (122)Excellent
    3.2 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.5 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Air Conditioning
    • Washer
    • Parking
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious home with a large outside deck is tucked away on a quiet lane in the Truman Annex, yet only a short walk to all attractions. Artist Garden makes an ideal vacation rental for those who like to enjoy a Duval crawl and a quiet peaceful vacation at the same time. A bright and breezy 2...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Parking
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just steps away from Harry Truman's 'Little White House' you’ll find your vacation dreams come true! Located in the historic brick Foundry building, Key West Found is a spacious two bedroom, two and a half bath, three-story town home. Enter through a wrought iron gate to your own tropical...
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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
    0.8 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Parking
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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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
    1.6 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Parking
    • Internet Access
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
    0.5 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch. This lovely Truman Annex condo rental in the exclusive...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    0.5 kilometres from Sunset Pier
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home. At Easy Livin' the name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    0.6 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Garden
    • Washer
    • Cable/satellite TV
    • Balcony
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-minute walk will take you to the iconic Duval Street, the heart of Key West. The unit located on the first floor has three-dimensional ceilings throughout with indirect LED...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Truman Annex: The Plantation SELF CATERING  beautifully landscaped rear patio1 / 17
    (65)Excellent
    0.8 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check-in Check-out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fully renovated house is located in the historic seaport with many highly rated restaurants and shops. A quick 5-minute walk will take you to the iconic Duval Street, the heart of Key West. The unit located on the second floor has three-dimensional ceilings throughout with indirect LED...
    View all property information
    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
    Truman Annex Best Location in Town1 / 31
    (27)Excellent
    0.9 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Check-in Check-out
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Washer
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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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
    (179)Excellent
    0.9 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    stayz logo
    Check-in Check-out
    Show Prices
    Amenities & Details
    • Internet Access
    • Washer
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Superb Location, Affordably Priced1 / 50
    (149)Excellent
    0.9 kilometres from Sunset Pier
    Studio, 1 Bathroom, Sleeps 1 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 1
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