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

Southernmost Vistas By Last Key Realty

1327 Whitehead Street, Key West, United States Show map

Staying at the 4-bedroom Southernmost Vistas By Last Key Realty Key West villa, guests can easily reach Key West Aquarium, located just 1.2 km away. With a maximum capacity of 10 guests, the Key West… More

From US$ 528 Book Now

Contra House -Luxury Home With Pool

Simonton Street 720, Key West, United States Show map

Offering an outdoor swimming pool, the 4-bedroom Contra House -Luxury Home With Pool Key West is situated merely 7 minutes' walk from The Ernest Hemingway Home and Museum and can accommodate up to 12… More

From US$ 1909 Book Now

Pegasus International Hotel

501 Southard Street, Key West, United States Show map

The 3-star Pegasus International Hotel Key West is situated in a busy area of Key West, merely 1 km from Key West Butterfly and Nature Conservatory and only 5 minutes' walk from Nancy Forrester's… More

From US$ 114 Book Now

Keys Please!

Louisa Street 514, Key West, United States Show map

Keys Please! Villa Key West accommodates guests in the Duval district, a 12-minute walk from the vintage parish "Saint Paul's Episcopal Church of Key West", and offers a private garden for guests to… More

From US$ 1910 Book Now

The Green Gawdess

1325 Whitehead Street, Key West, United States Show map

Up to 8 guests can stay at the 4-bedroom The Green Gawdess Key West villa and enjoy Key West Lighthouse and Keeper's Quarters Museum, located about a 5-minute walk away. The property features… More

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Louisa House

521 Louisa Street, Key West, United States Show map

Offering a swimming pool, the 4-bedroom Louisa House Villa Key West is situated just a 6-minute walk from Southernmost Point of the Continental US Monument and can accommodate up to 10 guests. This 1… More

From US$ 1399 Book Now

Diamond Girl By Last Key Realty

62 Front Street, Key West, United States Show map

Situated merely an 8-minute stroll from Key West Aquarium, the 4-bedroom Diamond Girl By Last Key Realty Key West villa is suitable for 8 guests and provides a swimming pool to relax in. Offering a… More

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Kw121Flr Casa Hueso

1321 Whitehead Street, Key West, United States Show map

Featuring a heated pool, Kw121Flr Casa Hueso Villa Key West is suitable for up to 8 people and is located a 17-minute walk from Nancy Forrester's Secret Garden. This 4-bedroom villa features… More

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Ecco Domani By Avantstay

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

Located only 6 minutes' walk from The Ernest Hemingway Home and Museum, the 3-bedroom Ecco Domani By Avantstay Key West villa boasts an outdoor swimming pool and can accommodate up to 6. Providing… More

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Absolutely Paradise

1011 Simonton Street #3, Key West, United States Show map

Located around 5 minutes on foot from The Ernest Hemingway Home and Museum, the 3-bedroom Absolutely Paradise Key West villa can accommodate up to 8 guests, providing them with a sauna for a relaxing… More

From US$ 1973 Book Now

Coconut Cabana

523 Louisa Street, Key West, United States Show map

Along with proximity to Southernmost Point of the Continental US Monument, just 500 metres away, the 3-bedroom Coconut Cabana Key West offers opportunities for windsurfing, snorkelling, and canyoning… More

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Kw378Flr Periwinkle Place

604 Truman Ave, Key West, United States Show map

The 1-bedroom Kw378Flr Periwinkle Place Key West villa, located just 5 minutes' walk from the historic Key West Lighthouse, can host up to 4 guests. This property features opportunities for… More

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Kw255Flr Louisa

522 Louisa St (Lower Level), Key West, United States Show map

Along with proximity to The Ernest Hemingway Home and Museum, just 0.6 km away, the 1-bedroom Kw255Flr Louisa Villa Key West offers opportunities for snorkelling, diving, and fisheries in the area. More

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Marreros Guest Mansion - Adult Only

410 Fleming Street, Key West, United States Show map

Featuring 12 rooms, the 2-star Marreros Guest Mansion - Adult Only Bed & Breakfast Key West is located near the beach district of Key West and about 700 metres from the waterfront Mallory Square. More

From US$ 235 Book Now

Kw335Wk Dancing Palms

606 Truman Ave 9, Key West, United States Show map

Featuring an outdoor swimming pool, the 2-bedroom Kw335Wk Dancing Palms Villa Key West is suitable for up to 4 people and is located nearly a 25-minute walk from Fort Zachary Taylor. The villa boasts… More

From US$ 533 Book Now

Baya House

606 Truman Ave, #13, Key West, United States Show map

Situated within 5 minutes' walk of Saint Mary Star of the Sea Basilica, Baya House Villa Key West offers easy access to numerous tourist spots in the area. More

From US$ 321 Book Now

Breezy Retreat

606 Truman Avenue, Key West, United States Show map

Featuring an outdoor swimming pool, Breezy Retreat Villa Key West is suitable for up to 4 people and is located a 16-minute walk from Key West Aquarium. Providing guests with Wi-Fi and parking, this… More

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Weatherstation Inn Circa 1911

57 Front Street, Key West, United States Show map

Situated merely 1.5 km from the 19-acre Key West Cemetery, the 2-star Weatherstation Inn Circa 1911 Key West features Wi-Fi in public areas, and private car parking on site. This Key West hotel is in… More

From US$ 169 Book Now

Truman Hotel

611 Truman Avenue, Key West, United States Show map

The 3-star Truman Hotel Key West, located merely a 9-minute walk from the downtown commercial zoned Duval Street and about 2 km from Key West Garden Club, features a heated pool for guests to take a… More

From US$ 224 Book Now

Dolphin Watch

100-1 Eaton Street, Key West, United States Show map

Dolphin Watch Villa Key West boasts an aqua park and a golf course and enjoys its location in the Downtown Key West district, 6 minutes' walk from Audubon House and Tropical Gardens. Located 2.1 km… More

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Key West Conch

707 Simonton Street, Key West, United States Show map

Situated right around the corner from Key West Lighthouse and Keeper's Quarters Museum, the 3-bedroom Key West Conch Villa provides access to numerous tourist attractions in the area. This Key West… More

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Sirens Serenade By Last Key Realty

66 Front Street, Key West, United States Show map

Staying at the 4-bedroom Sirens Serenade By Last Key Realty Key West villa, guests can easily reach Key West Garden Club, located nearly a 25-minute walk away. With a maximum capacity of 8 guests… More

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Avalon Bed And Breakfast (Adults Only)

1317 Duval Street, Key West, United States Show map

Located merely 1 km from the downtown commercial zoned Duval Street, Avalon Bed And Breakfast Key West is a mere 5 minutes' walk from Key West Butterfly and Nature Conservatory. Offering a plunge… More

From US$ 273 Book Now

Newly-Built, Dog-Friendly Home With Shared Pool - Walk To Beach & Dining

605 Virginia St, Key West, United States Show map

The 3-bedroom Newly-Built, Dog-Friendly Home With Shared Pool - Walk To Beach & Dining Key West provides easy access to various city attractions, such as Saint Mary Star of the Sea Basilica, situated… More

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Azure Vista Penthouse

401 Emma Street H, Key West, United States Show map

The 2-bedroom Azure Vista Penthouse Villa Key West, located around a 5-minute walk from US 1 Mile Marker 0, can host up to 6 guests. The villa features opportunities for snorkelling in the area, in… More

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Amelia Home By Avantstay

605 Amelia Street, Key West, United States Show map

Located a mere 8 minutes' walk from The Ernest Hemingway Home and Museum, the welcoming Amelia Home By Avantstay Key West is suitable for 6 guests and provides an outdoor swimming pool to relax in. More

From US$ 903 Book Now

Tropical Dreaming By Avantstay

607 Amelia St, Key West, United States Show map

Overlooking the pool, the welcoming Tropical Dreaming By Avantstay Key West villa enjoys a prime setting a 6-minute walk from the Minor Saint Mary Star of the Sea Basilica. Offering parking as well… More

From US$ 2051 Book Now

Parrotville

606 Truman Ave #12, Key West, United States Show map

Featuring a swimming pool, the spacious 2-bedroom Parrotville Key West apartment is within 5 minutes' walk of The Ernest Hemingway Home and Museum. Also, windsurfing, snorkelling, and canyoning can… More

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Courtney'S Place Historic Cottages & Inns

720 Whitmarsh Lane, Key West, United States Show map

Featuring luggage storage, the 2-star Courtney'S Place Historic Cottages & Inns Key West lies merely 9 minutes' walk from The Ernest Hemingway Home and Museum. The guest house offers Wi-Fi in public… More

From US$ 219 Book Now

Southernmost Inn Adult Exclusive

525 United St, Key West, Fl, Key West, United States Show map

Offering a hot tub and a sunbathing terrace, the 3-star Southernmost Inn Adult Exclusive Key West is nestled in Duval with leather arm chairs and couches all surrounded by glimmering candles and chic… More

From US$ 109 Book Now

Tumis Time Out By Avantstay

606 Truman Ave #4, Key West, United States Show map

Located in the Duval district, a 6-minute walk from Saint Mary Star of the Sea Basilica, Tumis Time Out By Avantstay Key West villa offers pool views. Providing guests with Wi-Fi and parking, the 2… More

From US$ 251 Book Now

Villa Cubana By Last Key Realty

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

Located within a 700-metre distance of the downtown commercial zoned Duval Street, Villa Cubana By Last Key Realty Key West is suitable for 4 guests and provides a swimming pool to relax in. Located… More

From US$ 848 Book Now

Old Town Main House Guest House Close To Duval

614 Virginia Street, Key West, United States Show map

Staying at the 2-bedroom Old Town Main House Guest House Close To Duval Key West villa, guests can visit US 1 Mile Marker 0, which is just 0.8 km away. More

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New Kamp - Rooftop Penthouse

Fleming Street 430, Key West, United States Show map

Offering an aqua park and a golf course, the 1-bedroom New Kamp - Rooftop Penthouse Key West apartment is located in Duval with leather arm chairs and couches all surrounded by glimmering candles and… More

From US$ 1477 Book Now

Southernmost Point Guest House & Garden Bar

1327 Duval Sreet, Key West, United States Show map

Offering a terrace and a picnic area, Southernmost Point Guest House & Garden Bar Key West lies in Duval with leather arm chairs and couches all surrounded by glimmering candles and chic decor, 17… More

From US$ 253 Book Now

The Collins On Duval

Duval Street 505, Key West, United States Show map

Set in Duval with one of Key West's top culinary experiences, a 9-minute walk from the historical Key West Lighthouse, the spacious The Collins On Duval Apartment Key West accommodates up to 8 guests… More

From US$ 655 Book Now

The Conch House Heritage Inn

625 Truman Ave, Key West, United States Show map

Offering luggage storage, The Conch House Heritage Inn Key West lies in the Downtown Key West district, about 500 metres from Key West Lighthouse and Keeper's Quarters Museum and 16 minutes' walk… More

From US$ 345 Book Now

Knot A Worry

625 Simonton Street, Key West, United States Show map

Located just 8 minutes' walk from the vintage parish "Saint Paul's Episcopal Church of Key West", Knot A Worry Villa Key West offers a swimming pool for guests to relax by. The villa features… More

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Duval Dream Loft On Duval

Duval Street 503, Key West, United States Show map

The welcoming 150 m² Duval Dream Loft On Duval Apartment Key West features a prime location just 500 metres from The Oldest House Historical Place Museum and hosts up to 8 guests. This spacious… More

From US$ 627 Book Now

Villa Bahama By Last Key Realty

101 Front Street #11, Key West, United States Show map

Located 9 minutes' walk from Mile Marker 0 Store, Villa Bahama By Last Key Realty Key West is suitable for 6 guests and provides a swimming pool to relax in. Located 2.3 km from Key West Garden Club,… More

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Elizabeth'S Secret - Old Town Key West

910 Elizabeth St, Key West, United States Show map

Nestled an 18-minute walk from Papa's Pilar Rum Distillery, Elizabeth'S Secret - Old Town Key West Villa entices guests to explore various tourist destinations nearby. More

From US$ 1566 Book Now

Conch Easy Livin'

617 Simonton Street, Key West, United States Show map

Situated in the Duval district of Key West, within 15 minutes' walk of Saint Mary Star of the Sea Basilica, the 2-bedroom Conch Easy Livin' Villa Key West comes with a heated pool for guests to… More

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Key West Found By Avantstay

101 Front St #13, Key West, United States Show map

Staying at the 2-bedroom Key West Found By Avantstay villa, guests can visit Saint Mary Star of the Sea Basilica, which is just 1.7 km away. Offering parking as well as Wi-Fi, the welcoming holiday… More

From US$ 544 Book Now

The Royal Compound By Last Key Realty

101 Admirals Lane, Key West, United States Show map

Featuring a swimming pool, The Royal Compound By Last Key Realty Key West villa is suitable for up to 8 people and is located 5 minutes' drive from South Beach. Providing guests with Wi-Fi and… More

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Southernmost House - Adult Exclusive

1400 Duval Street, Key West, United States Show map

The smoke-free Southernmost House - Adult Exclusive Key West hotel is situated in Duval with one of Key West's top culinary experiences, about a 10-minute walk from The Ernest Hemingway Home and… More

From US$ 232 Book Now

Kw143Flr Olivia Street Retreat

630 Olivia Street, Key West, United States Show map

The 1-bedroom Kw143Flr Olivia Street Retreat Villa Key West offers quick access to such city attractions as the 19 - acre Key West Cemetery, located just a 6-minute walk away. Offering a prime… More

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H2O Suites- Adults Only

1212 Simonton Street, Key West, United States Show map

The 4-star smoke-free H2O Suites- Adults Only Key West hotel is only 1.7 km from Higgs Beach Dog Park and boasts a sunbathing terrace, a shared lounge, and a golf course. Offering a heated pool, the… More

From US$ 299 Book Now

1 Island Time Escape

101 Front Street, #15, Key West, United States Show map

Situated nearly a 5-minute stroll from the Harry S. Truman Little White House, the 2-bedroom 1 Island Time Escape Villa Key West ensures a great leisure experience by offering snorkelling and… More

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Jasmine Jule By Last Key Realty

108 Admirals Lane, Key West, United States Show map

Situated only 5 minutes' stroll from the bustling plaza "Mallory Square", the 2-bedroom Jasmine Jule By Last Key Realty Key West villa is suitable for 6 guests and provides a swimming pool to relax… More

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A License To Chill

101 Front Street, #12, Key West, United States Show map

Located within a 700-metre distance of the waterfront Mallory Square, A License To Chill Villa Key West is suitable for 6 guests and provides an outdoor swimming pool to relax in. The 2-bedroom villa… More

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