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Holiday Rentals near Sunset Pier

Duval St, Ocean Key Resort & Spa, Key West, Florida 33040
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    R 7 906 Average
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 19 Rentals in Key West
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    0.8 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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    0.8 kilometres from Sunset Pier
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Garden
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location! Brand new and beautiful, this spacious house is conveniently located on a quiet street in the heart of Old Town Key West only 1/2 block from the fabulous shops, restaurants and bars that made Duval Street famous. Beautifully furnished and luxuriously appointed, Bahama...
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    Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    0.8 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    • Luxury 2nd & 3rd floor Penthouse • 3 Bedrooms with private porches & 2 1/2 Baths • 2200 square feet of living space • Over 2000 square feet of porches and decks • Backyard with tropical landscaping, pool & waterfall • Huge roof top sun deck overlooking Duval Street • off-street parking One...
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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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    • Housekeeping Included
    • Air Conditioning
    • Cable/satellite TV
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Sauna
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OCEANFRONT CONDO RENTAL 45 FT FROM THE WATER WITH BREATHTAKING VIEWS OF KEY WEST, SUNSET KEY AND THE GULF OF MEXICO Sleeps 6 / 1 Master King - 1 Guest Queen / 1 Queen pullout / Private Balcony EXCEPTIONAL LOCATION & CONVENIENCE On the ocean at the end of North Front St (literally steps from your...
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    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.4 kilometres from Sunset Pier
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Hot Tub
    • Waterfront
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    • Wi-Fi
    • Air Conditioning
    • Cable/satellite TV
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Amenities & Details
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 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
    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
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    0.3 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    0.5 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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    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
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • 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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    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.8 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table. Check out the history and architecture of Old Town. All these options and many more are yours...
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    Location Information
    Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    0.3 kilometres from Sunset Pier
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Balcony
    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Location Information
    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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    Amenities & Details
    • Washer
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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
    0.6 kilometres from Sunset Pier
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    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
    0.8 kilometres from Sunset Pier
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Look No Further!! Bahamian Reed is the vacation rental home for those special vacation memories that you will come back to again and again. This two-bedroom, 1.5-bathroom, 2-story town home located in scenic Truman Annex in Old Town is conveniently located near all the reasons you came to Key West...
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    Location Information
    Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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