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2026-11-05
2026-11-06
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Hotels in Classic Harbor Line area of Florida

Sky Loft In Key West

Southard Street 611, Key West, United States Show map

Situated only 0.7 km from the very unusual Key West Cemetery, the 1-bedroom Sky Loft In Key West Villa is ideal for up to 4 guests. This Key West holiday home boasts an aqua park and a golf course… More

From US$ 512 Book Now

Trumans Hideaway By Avantstay

113 Front St #108, Key West, United States Show map

To enjoy your vacation in Key West, stay at the spacious 123 m² Trumans Hideaway By Avantstay Key West apartment, which is only 1.6 km from Fort Zachary Taylor and only 500 metres from Key West… More

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Aqua Breeze

105 Front Street #219, Key West, United States Show map

Offering a heated pool, the 2-bedroom Aqua Breeze Villa Key West is located approximately a 5-minute walk from the fully accredited Mel Fisher Maritime Heritage Museum and is ideal for up to 5 guests… More

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A Sunset Peace

109 Front Street #210, Key West, United States Show map

Offering a heated pool, the 2-bedroom A Sunset Peace Villa Key West is located nearly a 5-minute walk from Audubon House and Tropical Gardens and is ideal for up to 4 guests. The holiday home… More

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Tropical Executive

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

Located only a 9-minute stroll from the bustling plaza "Mallory Square", the 2-bedroom Tropical Executive Villa Key West provides a heated pool as well as snorkelling and fisheries to diversify… More

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Saltwater Angler

115 Front Street #203, Key West, United States Show map

Providing guests with an aqua park and a golf course to ensure a memorable stay, the 2-bedroom Saltwater Angler Villa Key West is merely a 9-minute walk from the waterfront Mallory Square. Located in… More

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Colony Poolside

714 Olivia Street, Key West, United States Show map

Located just 500 metres from Southernmost Point of the Continental US Monument, the 1-bedroom Colony Poolside Villa Key West offers opportunities for windsurfing, snorkelling, and canyoning in the… More

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Sweet'S Spot

109 Front Street #309, Key West, United States Show map

Located just around the corner from the Harry S. Truman Little White House, Sweet'S Spot Villa Key West boasts an outdoor swimming pool and can accommodate up to 6. The 3-bedroom holiday home… More

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Paradise On The Ocean

105 Front Street #218, Key West, United States Show map

Located only 550 metres from Mile Marker 0 Store, the 2-bedroom Paradise On The Ocean Key West villa offers opportunities for snorkelling and fisheries in the area. This Key West holiday home hosts… More

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Sundown Refuge By Avantstay

113 Front St #107, Key West, United States Show map

The 2-bedroom Sundown Refuge By Avantstay Key West apartment is situated merely a 6-minute walk from Key West Shipwreck Treasure Museum and 5 km from Key West International airport. While staying in… More

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A Gulfstream Drift

105 Front Street #319, Key West, United States Show map

Situated a mere 9 minutes on foot from the waterfront Mallory Square, the 2-bedroom A Gulfstream Drift Villa Key West is suitable for 7 guests and provides a heated pool to relax in. Offering a lift… More

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Forever Young

115 Front Street, #202, Key West, United States Show map

The 2-bedroom Forever Young Key West villa is situated nearly 5 minutes' walk from Front Street, featuring such comforts as Wi-Fi and a private parking lot. Offering a prime location in the Downtown… More

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A Sunset And Harbour View

115 Front Street #204, Key West, United States Show map

Featuring an outdoor swimming pool, the 2-bedroom A Sunset And Harbour View Villa Key West is located merely 6 minutes' walk from Key West Shipwreck Treasure Museum and is suitable for up to 6 guests… More

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Sunset Dalite

109 Front Street #212, Key West, United States Show map

Situated approximately 5 minutes' walk from the fully accredited Mel Fisher Maritime Heritage Museum, the 2-bedroom Sunset Dalite Villa Key West is ideal for up to 4 guests. Providing guests with Wi… More

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A Harbour Roost

109 Front Street #114, Key West, United States Show map

Located just 0.6 km from the vintage parish "Saint Paul's Episcopal Church of Key West", the 2-bedroom A Harbour Roost Villa Key West has an outdoor swimming pool and is ideal for up to 5 guests. More

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Harveys Haven

611 Southard St #2, Key West, United States Show map

The spacious 44 m² Harveys Haven Apartment Key West is located only 0.8 km from the 19-acre Key West Cemetery and offers Wi-Fi for either business or leisure. Providing a prime setting in Key West… More

From US$ 375 Book Now

Southernmost Sanctuary All

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

The 6-bedroom Southernmost Sanctuary All Key West villa hosts up to 24 guests and provides proximity to the even Southernmost Point, situated only 5 minutes' stroll away. More

From US$ 6938 Book Now

Osprey Suite | Charming Hideaway, Hot Tubs!

1330 Simonton Street #4, Key West, United States Show map

The 1-bedroom Osprey Suite | Charming Hideaway, Hot Tubs! Key West villa offers swift access to various city sites, such as the secluded pocket Dog Beach, situated approximately a 5-minute walk away.… More

From US$ 321 Book Now

Heron Suite | Vibrant Retreat, Hot Tubs, Steps From Duval

1330 Simonton Street #2, Key West, United States Show map

The 1-bedroom Heron Suite | Vibrant Retreat, Hot Tubs, Steps From Duval Key West villa hosts up to 4 guests and provides proximity to the even Southernmost Point, situated just 5 minutes' walk away. More

From US$ 219 Book Now

Egret Suite | Bright Retreat, Hot Tubs, Steps From Duval!

1330 Simonton Street #1, Key West, United States Show map

The 1-bedroom Egret Suite | Bright Retreat, Hot Tubs, Steps From Duval! Key West villa accommodates up to 4 guests and offers proximity to the even Southernmost Point, located merely a 5-minute walk… More

From US$ 354 Book Now

Ibis Suite | Bright Hideaway, Hot Tubs, Steps From Duval!

1330 Simonton Street #3, Key West, United States Show map

Situated within 5 minutes' walk of the even Southernmost Point, the 1-bedroom Ibis Suite | Bright Hideaway, Hot Tubs, Steps From Duval! Key West villa offers easy access to numerous tourist spots in… More

From US$ 766 Book Now

Pelican Suite | Cozy Cottage, Hot Tubs, Close To D

1330 Simonton Street #5, Key West, United States Show map

Situated about 25 minutes' walk from the Harry S. Truman Little White House, the 1-bedroom Pelican Suite | Cozy Cottage, Hot Tubs, Close To D Key West provides access to numerous tourist attractions… More

From US$ 620 Book Now

Seagull Suite | Inviting Studio, Steps From Duval

Simonton Street, Key West, United States Show map

Staying at the 1-bedroom Seagull Suite | Inviting Studio, Steps From Duval Key West villa, guests can visit the natural history museum "Florida Keys Eco-Discovery Center", which is just 1.8 km away. More

From US$ 461 Book Now

Ole' Olivia

716 Olivia Street, Key West, United States Show map

Located just a 5-minute walk from The Ernest Hemingway Home and Museum, Ole' Olivia Villa Key West is suitable for 8 guests and provides a heated pool to relax in. More

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Southernmost Sanctuary

1330 Simonton Street, Key West, United States Show map

Situated a 10-minute drive from Fort Zachary Taylor, Southernmost Sanctuary Key West villa entices guests to explore various tourist attractions in the area. More

From US$ 118 Book Now

Casa Azul-Open Concept Home With Pool

Elizabeth Street 629, Key West, United States Show map

Situated in the Downtown Key West district of Key West, just 550 metres from San Carlos Institute, the 2-bedroom Casa Azul-Open Concept Home With Pool Key West comes with a swimming pool for guests… More

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Island Pearls

527 Fleming Street, Key West, United States Show map

The 2-bedroom Island Pearls Villa Key West accommodates up to 4 guests and offers proximity to Nancy Forrester's Secret Garden, located only a 9-minute walk away. The property features opportunities… More

From US$ 1551 Book Now

Catch Of The Day

113 Front Street #106, Key West, United States Show map

The 3-bedroom Catch Of The Day Villa Key West entices guests to enjoy snorkelling and fisheries and offers proximity to the bustling plaza "Mallory Square", located only 9 minutes' stroll away. The… More

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Winslow'S Bungalows - Key West Historic Inns

725 Truman Avenue, Key West, United States Show map

The 4-star smoke-free Winslow'S Bungalows - Key West Historic Inns is about a 10-minute stroll from South Beach and offers a swimming pool. Located within a few blocks of Mile Marker 0 Store, this… More

From US$ 139 Book Now

Casa Lima

718 Windsor Lane, Key West, United States Show map

During the stay at Casa Lima Villa Key West, guests can indulge in windsurfing, snorkelling, and canyoning or visit the downtown commercial zoned Duval Street, located a 13-minute walk away. The 2… More

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The Marquesa Hotel

600 Fleming Street, Key West, United States Show map

Featuring Wi-Fi throughout the property, The Marquesa Hotel Key West is a 10-minute walk from the very unusual Key West Cemetery. Guests can take advantage of a private parking lot at additional… More

From US$ 440 Book Now

Paradise Found

711 William Street, Key West, United States Show map

Offering a steam room and a sauna for a relaxing experience, Paradise Found Key West villa is located an 18-minute walk from the waterfront Mallory Square. The 2-bedroom holiday home features… More

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Conch House

330 Caroline Street, Key West, United States Show map

The 4-bedroom Conch House Villa Key West hosts up to 8 guests and provides proximity to the bustling plaza "Mallory Square", situated only a 7-minute walk away. The accommodation features… More

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Old Town Manor

511 Eaton Street, Key West, United States Show map

Situated merely 0.9 km from the historical Key West Lighthouse, the 3-star smoke-free Old Town Manor Bed & Breakfast Key West features Wi-Fi in the rooms, and public parking nearby. Staying at this… More

From US$ 154 Book Now

The Admirals Estate By Last Key Realty

324 Whitehead Street, Key West, United States Show map

Offering a heated pool, the 4-bedroom The Admirals Estate By Last Key Realty Key West villa is situated a mere 8 minutes' walk from US 1 Mile Marker 0 and can accommodate up to 8 guests. Located a… More

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The Toasted Coconut By Last Key Realty

423 Simonton Street, Key West, United States Show map

Situated nearly a 5-minute stroll from Key West Historic Seaport, the 3-bedroom The Toasted Coconut By Last Key Realty Key West villa is suitable for 8 guests and provides a swimming pool to relax in… More

From US$ 798 Book Now

The Lime And The Coconut By Last Key Realty

421-423 Simonton Street, Key West, United States Show map

Situated approximately 5 minutes' walk from Vandenberg Wreck, the 6-bedroom The Lime And The Coconut By Last Key Realty Key West villa is ideal for up to 16 guests. More

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Casa 325 Guesthouse

325 Duval Street, Key West, United States Show map

Offering a swimming pool, Casa 325 Guesthouse Key West is situated in Duval with one of Key West's top culinary experiences, 8 minutes' walk from Mile Marker 0 Store. Boasting a location in proximity… More

From US$ 285 Book Now

The Zesty Lime By Last Key Realty

421 Simonton Street, Key West, United States Show map

Staying at the 3-bedroom The Zesty Lime By Last Key Realty Key West villa, guests can visit Mile Marker 0 Store, which is only 0.8 km away. The Key West holiday home features a heated pool and is… More

From US$ 2356 Book Now

Casa Amor

723 Catherine Street, Key West, United States Show map

Casa Amor Key West is located an 8-minute walk from Higgs Beach and offers guests to enjoy windsurfing, snorkelling, and canyoning. Offering a prime location in the Downtown Key West district, the 3… More

From US$ 1929 Book Now

Santa Maria Suites Resort

1401 Simonton Street, Key West, United States Show map

The 4-star Santa Maria Suites Resort Key West is located approximately 20 minutes' walk from the historic fort "West Martello Tower" and offers a restaurant. Boasting a location just around the… More

From US$ 190 Book Now

Tennessee Williams By Avantstay

709 Bakers Lane, Key West, United States Show map

Offering pool views, Tennessee Williams By Avantstay Key West villa is situated a 5-minute walk from the downtown commercial zoned Duval Street. Providing guests with Wi-Fi and a car park, the 2… More

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Monkey House By Avantstay

709 Bakers Lane, Key West, United States Show map

Offering an outdoor swimming pool, the 2-bedroom Monkey House By Avantstay Key West villa is located merely 0.6 km from Key West First Legal Rum Distillery and is ideal for up to 4 guests. Providing… More

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The Key West Hotel

325 Duval Street, Key West, United States Show map

The comfortable The Key West Hotel, located in Duval with one of Key West's top culinary experiences, about 20 minutes' walk from Alan S Maltz Gallery, features views of the pool. Offering an outdoor… More

From US$ 1090 Book Now

Valhalla - Southernmost Oasis

641 United St, Key West, United States Show map

Situated just a 6-minute stroll from Key West Butterfly and Nature Conservatory, the 2-bedroom Valhalla - Southernmost Oasis Key West villa is suitable for 4 guests and provides a swimming pool to… More

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Ambrosia Key West

622 Fleming Street, Key West, United States Show map

The 3-star Ambrosia Key West Motel is located near the entertainment district of Key West, merely 6 minutes' walk from US 1 Mile Marker 0. Opened in 1903, the motel with air-conditioned rooms and 3… More

From US$ 299 Book Now

Boat House By Avantstay

711 Bakers Lane, Key West, United States Show map

Located merely 6 minutes' walk from the downtown commercial zoned Duval Street, Boat House By Avantstay Key West villa features an outdoor swimming pool and can accommodate up to 2 guests. This 1… More

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Simonton Court Historic Inn & Cottages

523 Eaton Street, Key West, United States Show map

Simonton Court Historic Inn & Cottages Key West is a great place to stay in Duval with leather arm chairs and couches all surrounded by glimmering candles and chic decor, an 18-minute walk from Key… More

From US$ 175 Book Now

The Mermaid & The Alligator - Adult Only

729 Truman Avenue, Key West, United States Show map

The Mermaid & The Alligator - Adult Only Key West hotel is a great place to stay in the Downtown Key West district, a 20-minute walk from the Harry S. Truman Little White House. This hotel features… More

From US$ 256 Book Now

The Artist House

534 Easton Street, Key West, United States Show map

Featuring Wi-Fi in public areas, The Artist House Bed & Breakfast Key West sits a 15-minute walk from Alan S Maltz Gallery. Located 3.1 km from Smathers Beach, this hotel offers views of the garden… More

From US$ 125 Book Now