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2026-11-15
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Hotels in Key West near Classic Harbor Line

Bootlegger Bay @ Speakeasy Inn Key West!

1117 Duval St., Key West, United States View map

Situated nearly 5 minutes' walk from the comfortable Bootlegger Bay @ Speakeasy Inn Key West!, guests can reach the Key West Butterfly and Nature Conservatory in no time. This Key West guest house… More

From US$ 347 Book Now

Hideaway @ Speakeasy Inn Key West!

1117 Duval St., Key West, United States View map

Located only 400 metres from the South Beach, the comfortable Hideaway @ Speakeasy Inn Key West! offers Wi-Fi in the rooms and a car park. This Key West guest house lies in the Downtown Key West… More

From US$ 467 Book Now

Smuggler'S Cove @ Speakeasy Inn Key West!

1117 Duval St., Key West, United States View map

Featuring Wi-Fi in the rooms, the comfortable Smuggler'S Cove @ Speakeasy Inn Key West! is about a 20-minute walk from the Bayview Park. This guest house also includes a car park. More

From US$ 396 Book Now

Nightcap @ Speakeasy Inn Key West!

1117 Duval St., Key West, United States View map

Located around 400 metres from the Key West Lighthouse and Keeper's Quarters Museum, the comfortable Nightcap @ Speakeasy Inn Key West! is around 5 minutes' walk from the Key West Butterfly and… More

From US$ 376 Book Now

After Hours @ Speakeasy Inn Key West!

1117 Duval St., Key West, United States View map

After Hours @ Speakeasy Inn Key West!, located 18 minutes' walk from the Ripley's Believe It or Not, features Wi-Fi in the rooms. The guest house also includes parking. More

From US$ 344 Book Now

Night Watch @ Speakeasy Inn Key West!

1117 Duval St., Key West, United States View map

Located just 1.4 km from the USCGC Ingham Maritime Museum, the comfortable Night Watch @ Speakeasy Inn Key West! offers access to tourist attractions throughout Key West. The guest house also offers… More

From US$ 376 Book Now

Old Town Garden Villas

1001 Whitehead St., Key West, United States View map

Located 10 minutes' walk from the US 1 Mile Marker 0, Old Town Garden Villas Key West gives access to various tourist sites in the vicinity. More

From US$ 418 Book Now

Kw41 Amelia House

505 Amelia Street, Key West, United States View map

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Kw42 Bahama House

522 Bahama Street Key West Historic District, Key West, United States View map

Situated in the Downtown Key West district, a mere 1.9 km from the Fort Zachary Taylor, Bahama House Villa Key West comes with a swimming pool for guests to unwind. Guests can enjoy cycling and… More

From US$ 1932 Book Now

A Wave From It All

504 Porter Lane, Key West, United States View map

Situated just 9 minutes on foot from the downtown commercial zoned Duval Street, the 2-bedroom A Wave From It All Key West villa ensures a great leisure experience by offering snorkelling and fishing… More

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Paradise Found In The Center Of Old Town

907 Center St, Key West, Fl 33040, Key West, United States View map

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La Te Da - Adult Only, 21 Or Older

1125 Duval Street, Key West, United States View map

Experience the unparalleled beauty and charm of the La Te Da Hotel, an adult-only retreat nestled on the historic 1125 Duval Street. The property, crafted in 1892, is an establishment soaked in Key… More

From US$ 360 Book Now

Caribbean Cottage 28 Day Minimum Rental 2Br 2Ba Heated Pools

915 Center St, Key West, Fl 33040, Usa, Key West, United States View map

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Casa Bonita @ Duval Square R1

Key West, United States View map

To enjoy your vacation in Key West, stay at Casa Bonita @ Duval Square R1 Apartment Key West, which is nearly a 5-minute walk from the historical Key West Lighthouse and 2.3 km from the USCGC Ingham… More

From US$ 352 Book Now

Casa Key West-Pool & Free Parking

Duval Street 1075, Key West, United States View map

The 3-bedroom Casa Key West-Pool & Free Parking Villa accommodates up to 8 guests and offers proximity to Southernmost Point of the Continental US Monument, located merely a 5-minute walk away. More

From US$ 1170 Book Now

Villa Positano -Rooftop Pool On Duval

Duval Street 1075, Key West, United States View map

Villa Positano - Rooftop Pool On Duval Nestled in the vibrant heart of Duval, Villa Positano - Rooftop Pool On Duval presents a delightful blend of casual elegance and contemporary comfort. More

From US$ 762 Book Now

Kw72A Old Town Garden Villas - Abaco Suite

921 Center St., Key West, United States View map

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All Together Now By Last Key Realty

522-524-526 Dupont Lane, Key West, United States View map

Up to 32 guests can stay at All Together Now By Last Key Realty Key West villa and enjoy the even Southernmost Point, located 6 minutes' walk away. More

From US$ 6883 Book Now

Sweet Americana By Last Key Realty

524-526 Dupont Lane, Key West, United States View map

Sweet Americana By Last Key Realty Key West villa accommodates up to 20 guests and offers proximity to the downtown commercial zoned Duval Street, located just 7 minutes' walk away. More

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Summer Solstice By Last Key Realty

522-524 Dupont Lane, Key West, United States View map

Summer Solstice By Last Key Realty Key West villa offers swift access to various city sites, such as the Key West Lighthouse and Keeper's Quarters Museum, situated nearly a 5-minute walk away. More

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Casabella Duval Square

1075 Duval Street, Key West, United States View map

The 3-room Casabella Duval Square Apartment Key West is situated just a 6-minute walk from the even Southernmost Point and 5 km from Key West International airport. The spacious 115 m² apartment also… More

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Thalias Retreat

1075 Duval St #R23, Key West, United States View map

To enjoy your vacation in Key West, stay at the spacious 113 m² Thalias Retreat Apartment Key West, which is only 1.1 km from the 19 - acre Key West Cemetery and just moments from the Key West… More

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Bahama Breeze

416 Louisa Street, Key West, United States View map

The 3-bedroom Bahama Breeze Villa Key West offers swift access to various city sites, such as the Key West Lighthouse and Keeper's Quarters Museum, situated approximately a 5-minute walk away. Guests… More

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Elegant Escape By Last Key Realty

500 Emma Street, Key West, United States View map

**Welcome to the Elegant Escape By Last Key Realty, where luxury meets natural beauty in vibrant Key West.** Nestled just 10 km from Key West International Airport, this remarkable destination offers… More

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Andros Suite

921 Center Street #6, Key West, United States View map

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Road'S End - Old Town Garden Villas

921 Center Street #2, Key West, United States View map

The 1-bedroom Road'S End - Old Town Garden Villas Key West accommodates up to 4 guests and offers proximity to the Ernest Hemingway Home and Museum, located approximately a 5-minute walk away. More

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Endless Summer By Last Key Realty

522 Dupont Lane, Key West, United States View map

Endless Summer By Last Key Realty Key West villa offers quick access to such city attractions as Southernmost Point of the Continental US Monument, located just a 6-minute walk away. More

From US$ 3258 Book Now

Duval Square Penthouse

1075 Duval Street, Key West, United States View map

To enjoy your vacation in Key West, stay at the spacious 228 m² Duval Square Penthouse Apartment Key West, which is just 1.2 km from the shopping mall "Clinton Square Market" and approximately 10… More

From US$ 1378 Book Now

Pescado Penthouse

1201 Duval Street, Key West, United States View map

The 3-bedroom Pescado Penthouse Villa Key West, located just a 6-minute walk from the historic Key West Lighthouse, can host up to 9 guests. More

From US$ 1172 Book Now

Yellowfin Ledge

1201 Duval Street 2, Key West, United States View map

The 1-bedroom Yellowfin Ledge Key West villa, located merely a 6-minute walk from the historical Key West Lighthouse, can host up to 3 guests. More

From US$ 236 Book Now

Kingfish Keep

1201 Duval Street 3, Key West, United States View map

Situated just a 5-minute walk from Southernmost Point of the Continental US Monument, Kingfish Keep Villa Key West is ideal for up to 4 guests. More

From US$ 421 Book Now

Wahoo Way

1201 Duval Street 1, Key West, United States View map

**Wahoo Way Villa: A Caribbean Haven in Key West** Lastly, location is paramount at this exquisite villa. More

From US$ 227 Book Now

Pescado Penthouse On Duval

Key West, United States View map

Pescado Penthouse On Duval Villa Key West offers proximity to such city sites as the Key West Butterfly and Nature Conservatory, located approximately a 5-minute walk away. More

From US$ 191 Book Now

Casa De Cuba

518 Virginia Street, Key West, United States View map

Situated about 5 minutes' walk from the Ernest Hemingway Home and Museum, the 3-bedroom Casa De Cuba Villa Key West entices guests with windsurfing, snorkelling, and canoeing in the area. More

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Sea Esta Suite - Duval Square

1075 Duval Street R11, Key West, United States View map

The 115 m² Sea Esta Suite - Duval Square Key West is situated merely a 6-minute walk from Southernmost Point of the Continental US Monument and 5 km from Key West International airport. More

From US$ 748 Book Now

Casa Grande By Avantstay

515 Amelia Street, Key West, United States View map

Offering a swimming pool that comes with a patio, the welcoming Casa Grande By Avantstay Key West is located merely an 8-minute walk from the downtown commercial zoned Duval Street. Offering guests… More

From US$ 1074 Book Now

Duval Sea Turtle By Avantstay

1075-29 Duval Square, Key West, United States View map

Located only 6 minutes' walk from the Key West Aquarium, the 1-bedroom Duval Sea Turtle By Avantstay Key West villa boasts a swimming pool, a hot tub for a relaxing experience. Offering Wi-Fi, this… More

From US$ 551 Book Now

Duval Breeze By Avantstay

1075 Duval St #30, Key West, United States View map

The welcoming Duval Breeze By Avantstay Key West villa provides easy access to various city attractions, such as the Key West Butterfly and Nature Conservatory, situated merely 6 minutes' walk away. More

From US$ 1572 Book Now

New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool

Duval Street 1075, Key West, United States View map

Up to 6 guests can stay at the 2-bedroom New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool Key West and enjoy the Key West Lighthouse and Keeper's Quarters Museum, located approximately a 5… More

From US$ 343 Book Now

New! Villa Positano - Duval Square Condo, Pool, Hot Tub & Parking

Duval Street 1075, Key West, United States View map

**Welcome to Villa Positano - Duval Square Condo** Nestled in the vibrant heart of Duval, the Villa Positano presents an exquisite retreat blending contemporary elegance with a touch of coastal charm. More

From US$ 718 Book Now

Kw80Flr Paradise Suite

921 Center St, Key West, United States View map

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An Island Retreat

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

An Island Retreat Villa Key West is located 18 minutes' walk from Southernmost Point of the Continental US Monument and provides snorkelling and fishing for active guests. More

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Bonaire Suite

921 Center St #7, Key West, United States View map

Featuring a private pool, the 1-room Bonaire Suite Key West is just 6 minutes' walk from Southernmost Point of the Continental US Monument. The apartment with a patio is located within reach of the… More

From US$ 515 Book Now

Orchid Suite

921 Center St #4, Key West, United States View map

The 1-room Orchid Suite Key West features convenient proximity to such city attractions as the even Southernmost Point, situated a mere 6 minutes' walk away. A range of activities, such as… More

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Nassau Suite Key West

921 Center Street #12, Key West, United States View map

**Nassau Suite Key West** is nestled in the vibrant heart of Duval, offering an enchanting retreat that perfectly blends luxury with a lively atmosphere. This striking suite boasts elegant leather… More

From US$ 431 Book Now

Esperanza Suite

921 Center Street #9, Key West, United States View map

Nestled in the vibrant heart of Duval, the Esperanza Suite offers an enchanting retreat that embodies the essence of island living. More

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Gypsy'S Palace In The Truman Annex

401B Emma Street, Key West, United States View map

Situated in the Downtown Key West district, within 15 minutes' walk of the Papa's Pilar Rum Distillery, the 2-bedroom Gypsy'S Palace In The Truman Annex Key West villa comes with a swimming pool for… More

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Casa De Cubana

512 Amelia Street, Key West, United States View map

The 2-bedroom Casa De Cubana Villa Key West accommodates up to 4 guests and offers proximity to the Key West Butterfly and Nature Conservatory, located only a 7-minute walk away. More

From US$ 2269 Book Now

Afternoon Delight

401 Emma Street Apt F, Key West, United States View map

Located just a 9-minute walk from the downtown commercial zoned Duval Street, the 2-bedroom Afternoon Delight Villa Key West features a swimming pool and can accommodate up to 4 guests. This 2… More

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A Palm Oasis

405 Emma Street Unit B, Key West, United States View map

A Palm Oasis Villa Key West hosts up to 4 guests and provides proximity to the downtown commercial zoned Duval Street, situated 9 minutes' walk away. More

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