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2026-05-14
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Key West holiday rentals

Southernmost Hospitality VII By Last Key Realty

1224 Duval St, Key West, United States View map

The 8-bedroom Southernmost Hospitality VII By Last Key Realty Key West villa offers proximity to such city sites as Key West Lighthouse and Keeper's Quarters Museum, located nearly 5 minutes' walk… More

From US$ 3730 Book Now

Louisa House

521 Louisa Street, Key West, United States View map

**Welcome to Louisa House Villa Key West,** a vibrant oasis nestled in the heart of Duval Street. This enchanting retreat offers an unrivaled blend of island-inspired charm and modern amenities… More

From US$ 1399 Book Now

Soleil Chalet

1116 Varela, Key West, United States View map

The 3-bedroom Soleil Chalet Key West is located around a 20-minute walk from Duval Street and provides windsurfing, snorkelling, and canoeing for active guests. More

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Sirens Serenade By Last Key Realty

66 Front Street, Key West, United States View map

Located 6 km from Fort East Martello Museum, Sirens Serenade By Last Key Realty Key West villa gives access to various tourist sites in the vicinity. More

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A Southard Pearl

202-11 Southard Street, Key West, United States View map

A Southard Pearl Villa Key West offers quick access to such city attractions as the US 1 Mile Marker 0, located just a 6-minute walk away. More

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Gypsyginny'S Hideaway

900 White Street #2, Key West, United States View map

The 2-bedroom Gypsyginny'S Hideaway Key West villa provides easy access to various city attractions, such as The Unitarian Universalist Fellowship of Key West, situated approximately a 5-minute walk… More

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Island Pearls

527 Fleming Street, Key West, United States View map

Situated a mere 6 minutes' stroll from 7 Artists & Friends Gallery, the 2-bedroom Island Pearls Villa Key West offers quick access to numerous city landmarks nearby. More

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A Key West State Of Mind

49 Spoonbill Way, Key West, United States View map

A Key West State Of Mind Villa Stock Island offers swift access to various city sites, such as FYT Fitness Center, situated nearly 5 minutes' walk away. More

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Banana Breeze

2863 Key Cove Dr., Key West, United States View map

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From US$ 1576 Book Now

Away From It All

620 Thomas St., #283, Key West, United States View map

Away From It All Key West villa offers easy access to such tourist spots as the US 1 Mile Marker 0, located just a 6-minute walk away. More

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Sailor'S Story

564 Porter Lane, Key West, United States View map

Situated only 6 minutes' walk from the San Carlos Institute, Sailor'S Story Villa Key West offers easy access to numerous tourist spots in the area. More

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Casa Oliviana By Last Key Realty

803 Olivia Street, Key West, United States View map

Staying at the 4-bedroom Casa Oliviana By Last Key Realty Key West, guests can visit Key West Cemetery, which is merely a 13-minute walk away. More

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Sand Crab Cabana Weekly Rental!

620 Thomas Street, #269, Key West, United States View map

Sand Crab Cabana Weekly Rental! Key West offers easy access to such tourist spots as the US 1 Mile Marker 0, located just a 6-minute walk away. More

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Tropical Executive

107 Front Street #116, Key West, United States View map

Situated only 1.8 km from the Key West Butterfly and Nature Conservatory, Tropical Executive Villa Key West entices guests to explore various tourist attractions in the area. More

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Casa Atlantic

Key West, United States View map

Casa Atlantic Villa is approximately 15 minutes on foot from Southernmost Point and a 10-minute drive from from Key West Aquarium. While staying at the 3-bedroom villa, guests are welcome to use a… More

From US$ 258 Book Now

Paradise Found

711 William Street, Key West, United States View map

The 2-bedroom Paradise Found Key West villa offers swift access to various city sites, such as Key West Lighthouse and Keeper's Quarters Museum, situated approximately 5 minutes' walk away. This… More

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Another Three Hour Tour

620 Thomas Street #153, Key West, United States View map

Situated in close proximity to the Key West Lighthouse and Keeper's Quarters Museum, Another Three Hour Tour Key West villa offers easy access to numerous tourist spots in the area. More

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Ecco Domani By Avantstay

1011-2 Simonton St, Key West, United States View map

The 0-bedroom Ecco Domani By Avantstay Gorgeous Home W Pool Balcony In Great Location Month Long Stays Only Key West is located in close proximity to the Key West Lighthouse and Keeper's Quarters… More

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Scarlet At Scarlet Mango Inn Key West

603 Southard St., Key West, United States View map

Situated 5 minutes' walk from the Key West Express, Scarlet At Scarlet Mango Inn Key West offers a heated pool. More

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Bayview Middle

801 Eisenhower Dr. #5, 5, Key West, United States View map

Set in the enchanting landscapes of Key West, the Bayview Middle Villa seamlessly blends luxurious comfort with the captivating charm of the island. Just 10 km from Key West International Airport… More

From US$ 1078 Book Now

Dune Wind South By Avantstay

1901 S.Roosevelt Blvd 201S, Key West, United States View map

Situated 2.5 km from the Ernest Hemingway Home and Museum, Dune Wind South: Beachside Extended Stay with Pool & Hot Tub Key West villa entices guests to explore various tourist attractions in the… More

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Tortuga Suite By Last Key Realty

329 William Street #2, Key West, United States View map

Situated in the Downtown Key West district, 950 m from Key West Aquarium, the 1-bedroom Tortuga Suite By Last Key Realty Key West villa comes with a heated swimming pool for guests to unwind. More

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Knot A Worry

625 Simonton Street, Key West, United States View map

**Knot A Worry Villa Key West** is a luxurious retreat nestled in the vibrant heart of Duval Street, offering guests an exquisite blend of sophistication and comfort. This stunning villa captivates… More

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Tortugas Harbor Light Suite

419 Truman Avenue #2R, Key West, United States View map

**Welcome to Tortugas Harbor Light Suite, a charming retreat situated in the vibrant heart of Duval.** With its prime location, this splendid accommodation captures the essence of Key West's unique… More

From US$ 805 Book Now

Ahoy Mate!

210-1 Southard Street, Key West, United States View map

Offering a location merely a 10-minute walk from the arts theater "Red Barn Theatre", Ahoy Mate! Villa Key West gives access to various tourist spots in the area. More

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The Poetic Pineapple By Last Key Realty

4 Aronovitz Lane, Key West, United States View map

Staying at the 2-bedroom The Poetic Pineapple By Last Key Realty Key West villa, guests can easily reach Mel Fisher Maritime Heritage Museum, located a mere 14 minutes' walk away. More

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Casita Casa Marina

908 Flagler Avenue, Key West, United States View map

Offering a free private car park in the Downtown Key West district of Key West, the 3-bedroom Casita Casa Marina Villa Key West is also 950 m from significant religious sites like the Minor Saint… More

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Bachelorparty Hq For 16-Feet To Duval-Pool-Hot Tub

Truman Avenue 417, Key West, United States View map

The 4-bedroom Bachelorparty Hq For 16-Feet To Duval-Pool-Hot Tub Villa is situated in Key West, a 10-minute drive from Key West Garden Club and nearly a 9-minute walk from Mile Marker 0 Store. The… More

From US$ 1984 Book Now

Southernmost Palms By Last Key Realty

101 Front Street #24, Key West, United States View map

Situated around a 5-minute stroll from Ripley's Believe It or Not Museum, the 3-bedroom Southernmost Palms By Last Key Realty Key West villa offers quick access to numerous city landmarks nearby. More

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Queen Of Louisa By Last Key Realty

515 Louisa Street, Key West, United States View map

Situated just a 5-minute stroll from The Ernest Hemingway Home and Museum, the 4-bedroom Queen Of Louisa By Last Key Realty Key West villa offers quick access to numerous city landmarks nearby. More

From US$ 1649 Book Now

An Island Retreat

403B Emma Street, Key West, United States View map

An Island Retreat Villa Key West offers proximity to nearby tourist spots, such as the Mallory Square, situated about 15 minutes' walk away. More

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Island Time On The Green

19 Kingfisher Way, Key West, United States View map

Nestled a 15-minute drive from the vintage parish "Saint Paul's Episcopal Church of Key West", Island Time On The Green Stock Island villa entices guests to explore various tourist destinations… More

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Angelfish Reef By Last Key Realty

101 Front Street #8, Key West, United States View map

**Welcome to Angelfish Reef, an exquisite escape nestled in the heart of Key West, where luxury meets coastal charm. This stylish retreat boasts a breathtaking waterfront setting, perfect for… More

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Villa Cubana By Last Key Realty

606 Truman Avenue #5, Key West, United States View map

The 2-bedroom Villa Cubana By Last Key Realty Key West is located only a 12-minute walk from Southernmost Point of the Continental US, giving access to various tourist spots nearby. More

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Archipelago II

241 Southard Street, Key West, United States View map

Situated only 1.1 km from the Fort Zachary Taylor, Archipelago II Key West villa provides access to numerous tourist attractions in the area. More

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A Sunset Poolside

620 Thomas Street #156, Key West, United States View map

Located approximately a 10-minute walk from the Harry S. Truman Little White House, A Sunset Poolside Villa Key West provides access to various tourist attractions in the vicinity. More

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Colors Of The Keys By Last Key

101 Front Street #19, Key West, United States View map

The 3-bedroom Colors Of The Keys By Last Key Key West villa offers proximity to such city sites as Key West Shipwreck Treasure Museum, located just a 5-minute walk away. More

From US$ 663 Book Now

The Royal Compound By Last Key Realty

101 Admirals Lane, Key West, United States View map

Nestled in the lush paradise of Key West, The Royal Compound By Last Key Realty offers an idyllic retreat just 10 km from Key West International Airport. More

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Casa Caribe

506 Catherine St, Key West, United States View map

The 4-bedroom Casa Caribe Villa Key West is located a mere 0.9 km from the vintage parish "Saint Paul's Episcopal Church of Key West" and allows guests to enjoy windsurfing, snorkelling, and canoeing. More

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Corona At Azul Mansion Key West

907 Truman Ave., Key West, United States View map

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From US$ 523 Book Now

Ascension Truman Annex

225 Southard Street, Key West, United States View map

Ascension Truman Annex Key West villa is located 17 minutes' walk from the even Southernmost Point and invites guests to join snorkelling and fishing. More

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The Grande Vista

1800 Atlantic Blvd Unit C432, Key West, United States View map

The 2-room The Grande Vista Apartment Key West is located nearly 5 minutes' walk from The Key West Nature Preserve and overlooks the sea. Area attractions include South Beach, 2.5 km away, and Key… More

From US$ 818 Book Now

Island Paradise

413 Virginia St, Key West, United States View map

Featuring a year-round outdoor swimming pool for guests' enjoyment, Island Paradise Key West villa is nestled right in the centre of Key West, within a 300-metre distance of the Ernest Hemingway Home… More

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Southernmost Sanctuary All

1330 Simonton Street All, Key West, United States View map

Situated merely a 13-minute walk from Red Barn Theatre, Southernmost Sanctuary All Key West villa provides access to numerous tourist attractions in the area. More

From US$ 6938 Book Now

Luxury Residence In Old Town Key West W Pool

522 Simonton Street, Key West, United States View map

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Sailor'S Son

2867 Key Cove Dr., Key West, United States View map

**Sailor's Son Villa Key West is the perfect coastal escape where luxury meets the laid-back charm of island life. Located just 10 km from Key West International Airport, guests can effortlessly… More

From US$ 1325 Book Now

Harbor Walk Hideaways

Greene Street, Key West, United States View map

Situated in the Downtown Key West district, just 500 metres from The Studios of Key West Cultural Association, the 3-bedroom Harbor Walk Hideaways Villa Key West comes with a swimming pool for guests… More

From US$ 2171 Book Now

Prime Downtown Location - Truman Little Cozy Cottage

910 Simonton Street 3, Key West, United States View map

Situated 18 minutes' walk from the waterfront Mallory Square, Prime Downtown Location - Truman Little Cozy Cottage Key West entices guests to explore various tourist attractions in the area. More

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Casa Amarilla By Last Key Realty

516 Catherine Street, Key West, United States View map

The 2-bedroom Casa Amarilla By Last Key Realty Key West offers easy access to such tourist spots as Key West Lighthouse and Keeper's Quarters Museum, located a mere 5 minutes' walk away. More

From US$ 761 Book Now

Casita Olivietta By Last Key Realty

805 Olivia Street, Key West, United States View map

Situated just a 13-minute walk from Key West Firehouse Museum, the 5-bedroom Casita Olivietta By Last Key Realty Key West villa provides access to numerous tourist attractions in the area. More

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