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2026-03-22
2026-03-23
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Key West holiday rentals

Sweet Caroline

Caroline Street 537, Key West, United States View map

Sweet Caroline Villa offers accommodation just 400 metres from Simonton Beach, while Key West Aquarium is about a 5-minute stroll away. This villa is equipped with 2 bedrooms plus a kitchen with a… More

From US$ 932 Book Now

Osprey Suite - Southernmost Sanctuary

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

The 1-bedroom Osprey Suite - Southernmost Sanctuary Key West villa offers proximity to such city sites as Dog Beach, located just a 5-minute walk away. More

From US$ 450 Book Now

Windward Isle

531 Olivia St, Key West, United States View map

Only 10 minutes' walk from the Harry S. Truman Little White House, Windward Isle Villa is just off The Ernest Hemingway Home and Museum. This villa comprises 2 bedrooms and 1 bathroom. More

From US$ 312 Book Now

Harbor House Suite A

Front Street, Key West, United States View map

Located 14 minutes' walk from Nancy Forrester's Secret Garden, Harbor House Suite A Key West villa gives access to various tourist sites in the vicinity. More

From US$ 1520 Book Now

Ibis Suite - Southernmost Sanctuary

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

Conveniently located just steps from the vibrant nightlife and cultural attractions of Duval Street, the holiday home offers effortless transportation options. More

From US$ 766 Book Now

Atlantic Paradise Found

1800 Atlantic Blvd C232, Key West, United States View map

Welcome to Atlantic Paradise, a luxurious enclave nestled in the heart of Key West, where comfort meets coastal charm. Just a short 5 km from Key West International Airport, this exquisite retreat… More

From US$ 690 Book Now

A Siesta Bay By Avantstay Key West Walkable Gated Community Shared Pool Month-Long Stays

620 Thomas St #263, Key West, United States View map

Staying at the 1-bedroom A Siesta Bay By Avantstay Key West Walkable Gated Community Shared Pool Month-Long Stays villa, guests can visit the US 1 Mile Marker 0, which is only 500 metres away. More

From US$ 351 Book Now

Yellowfin Ledge

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

Situated around a 25-minute walk from White Street Pier, the 1-bedroom Yellowfin Ledge Key West villa provides access to numerous tourist attractions in the area. More

From US$ 432 Book Now

First Breath By Avantstay Close To Old Town W Pool Month Long Stays Only

1106 Eaton Street, Key West, United States View map

The 3-bedroom villa is just 1.2 km from Truman Little White House and less than 10 minutes on foot from from the Minor Saint Mary Star of the Sea Basilica. Guests, staying at this villa, can use an… More

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Oceanfront Oasis

1901 South Roosevelt Blvd, Unit 304, Key West, United States View map

Located a mere 5 minutes' stroll from the Higgs Beach Dog Park, the 2-bedroom Oceanfront Oasis Villa Key West comes with a heated swimming pool, a sauna. More

From US$ 550 Book Now

Sky Loft In Key West

Southard Street 611, Key West, United States View map

Positioned in the heart of Duval, the Sky Loft in Key West is an exquisite blend of laid-back luxury and sophisticated charm. This unique villa captures the essence of Key West while providing guests… More

From US$ 759 Book Now

Amelia Home By Avantstay In Historic Old Town W Pool

605 Amelia Street, Key West, United States View map

The 1-bedroom Amelia Home By Avantstay In Historic Old Town W Pool is a mere 1 km from Higgs Beach and it takes 10 minutes to drive to Key West International airport. Located in the Duval district… More

From US$ 903 Book Now

Southard Getaway By Avantstay W Covered Patio Great Location Shared Pool Month Long Stays

203 Southard #3, Key West, United States View map

Nestled 17 minutes' walk from the Southernmost Point, the welcoming Southard Getaway By Avantstay W Covered Patio Great Location Shared Pool Month Long Stays Key West villa entices guests to explore… More

From US$ 612 Book Now

Petes East Cottage

507 Louisa Street, Key West, United States View map

Situated merely a 5-minute stroll from The Ernest Hemingway Home and Museum, the 1-bedroom Petes East Cottage Key West ensures a great leisure experience by offering snorkelling, canoeing, and… More

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Conch In The Treetops By Last Key Realty

1800 Atlantic Blvd #C125, Key West, United States View map

Located around 25 minutes' walk from The Ernest Hemingway Home and Museum, the 2-bedroom Conch In The Treetops By Last Key Realty Key West villa entices guests to relax in a Jacuzzi. More

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Tranquility By The Beach

1800 Atlantic Blvd C129, Key West, United States View map

Situated approximately 5 minutes' walk from The Key West Nature Preserve, the 2-room Tranquility By The Beach Apartment Key West offers guests easy access to various tourist attractions nearby. The… More

From US$ 561 Book Now

Key Lime Calypso

409 Petronia Ave, Key West, United States View map

Key Lime Calypso Villa is situated in Key West, within a 5-minute walk of the downtown commercial zoned Duval Street and 15 minutes on foot from the secluded pocket Dog Beach. While staying at the 2… More

From US$ 333 Book Now

Conch Adventure By Avantstay Great Location W Outdoor Dining Pool Access Month-Long Stays

104 Southard Street #3, Key West, United States View map

Offering pool views, the 0-bedroom Conch Adventure By Avantstay Great Location W Outdoor Dining Pool Access Month-Long Stays Key West villa is situated a mere 10 minutes' walk from the Ernest… More

From US$ 369 Book Now

Somewhere On The Beach

1800 Atlantic Blvd, Unit C238, Key West, United States View map

The 2-bedroom Somewhere On Beach Villa is situated 15 minutes on foot from Higgs Beach in Key West and offers accommodation with an equipped kitchenette area. The property is located in Key West and… More

From US$ 972 Book Now

Darling Of Duval By Last Key Realty

425 Caroline Street, Key West, United States View map

Situated about a 5-minute stroll from Key West Historic Seaport, the 2-bedroom Darling Of Duval By Last Key Realty Key West villa provides guests with a Jacuzzi for additional relaxation. More

From US$ 1598 Book Now

Duval Hideaway

1124 Duval Street B, Key West, United States View map

**Discover the Duval Hideaway Villa in the Heart of Key West** Conveniently located, the villa is within walking distance to the bustling nightlife and unique shops that Duval Street is renowned for. More

From US$ 1284 Book Now

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

Duval Street 1075, Key West, United States View map

Situated in the Duval district, the 3-bedroom New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool right next to Key West Butterfly and Nature Conservatory and nearly 20 minutes' walk from the… More

From US$ 343 Book Now

Duval Street Retreat

1124 Duval Street A, Key West, United States View map

Located just 1.5 km from Memorial Sculpture Garden, the 1-bedroom Duval Street Retreat Villa Key West provides access to various tourist attractions in the vicinity. More

From US$ 1284 Book Now

Last Minute

Key West, United States View map

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From US$ 861 Book Now

Key West Light Suite

215 Eanes Lane, Key West, United States View map

The 1-bedroom Key West Light Suite villa provides easy access to various city attractions, such as the Ernest Hemingway Home and Museum, situated approximately 5 minutes' walk away. More

From US$ 853 Book Now

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$ 546 Book Now

New Grenada Suite - Parking Pool & Pets 209

Seaside Drive 3625, Key West, United States View map

New Grenada Suite - Parking Pool & Pets 209 is located at a 4.9 km distance from The Ernest Hemingway Home and Museum and 10 minutes' drive from Key West Firehouse Museum. This villa is equipped with… More

From US$ 513 Book Now

La Brisa Unit 105 North Building

South Roosevelt Boulevard 1901, Key West, United States View map

Higgs Beach is 1.2 km from La Brisa Unit 105 North Building Villa, while The Ernest Hemingway Home and Museum is a 10-minute drive from here. The 2-bedroom villa also comes with a kitchen, which is… More

From US$ 741 Book Now

The Breeze

1901 South Roosevelt Blvd, Unit 301 East, Key West, United States View map

During the stay at The Breeze Villa Key West, guests can indulge in a sauna or visit the Higgs Beach Dog Park, located 14 minutes' walk away. More

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Key West On My Mind

1800 Atlantic Blvd Unit A305, Key West, United States View map

Located just a 9-minute walk from Higgs Beach Dog Park and The Key West Nature Preserve, the 126 m^2 Key West On My Mind Apartment features views of the sea. More

From US$ 616 Book Now

Tranquility By Avantstay Close To Duval St W Bbq Shared Pool

714-5 Olivia St, Key West, United States View map

Located in the Downtown Key West district with The Ernest Hemingway Home and Museum nearby, the 1-bedroom Tranquility By Avantstay Close To Duval St W Bbq Shared Pool lies a mere 1.2 km from Higgs… More

From US$ 400 Book Now

Leo'S Lodge

1016 Howe St #7, Key West, United States View map

Located just a few steps from Key West Lighthouse and Keeper's Quarters Museum, the 1-bedroom Leo'S Lodge Key West offers quick access to various city attractions in the vicinity. More

From US$ 392 Book Now

Conch Cove

Simonton Lane 720, Key West, United States View map

The 2-bedroom Helen'S Hideaway Villa is set in Key West, a mere 300 metres from Nancy Forrester's Secret Garden and 0.9 km from South Beach. It includes WiFi throughout the property along with free… More

From US$ 2574 Book Now

Knowles House

1004 Eaton Street, Key West, United States View map

Situated in the Downtown Key West district, just 1.9 km from Dog Beach, Knowles House Villa Key West comes with a private swimming pool for guests to unwind. The villa is featuring a terrace with a… More

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Great Key West Location

100 Admirals Lane, Key West, United States View map

Great Key West Location Villa offers quick access to such city attractions as Key West Aquarium, located approximately a 5-minute walk away. More

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Soul Of Duval By Last Key Realty

615½ Duval Street, Unit 1, Key West, United States View map

Situated just 6 minutes' stroll from Southernmost Point of the Continental US Monument, Soul Of Duval By Last Key Realty Key West villa offers quick access to numerous city landmarks nearby. More

From US$ 1106 Book Now

Hemingway'S View

Key West, United States View map

The 3-bedroom Hemingway'S View Villa is located near The Ernest Hemingway Home and Museum, only 0.6 km from Southernmost Point. The property features a kitchen with a microwave, coffee/tea making… More

From US$ 1175 Book Now

Contra House -Luxury Home With Pool

Simonton Street 720, Key West, United States View map

Situated in Key West, at 750 metres of Key West Firehouse Museum, the 4-bedroom New Listing Palm Escape- Luxury Home W Pool provides accommodation with complimentary parking and a swimming pool. This… More

From US$ 1909 Book Now

Cohiba At Azul Mansion Key West

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

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Carey'S Corner

1016 Howe St #10, Key West, United States View map

The 1-bedroom Carey'S Corner Villa Key West offers swift access to various city sites, such as Southernmost Point, situated 500 metres away. More

From US$ 304 Book Now

The Mellow Macaw By Last Key Realty

1025D Whitehead Street, Key West, United States View map

The 1-bedroom The Mellow Macaw By Last Key Realty Key West villa offers swift access to various city sites, such as The Ernest Hemingway Home and Museum, situated nearly 5 minutes' walk away. More

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Ambrosia At Azul Mansion Key West

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

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From US$ 448 Book Now

Key West'S Best

1800 Atlantic Blvd, Unit C326, Key West, United States View map

Located just a 9-minute walk from the Higgs Beach Dog Park, the 2-bedroom Key West'S Best villa entices guests with a hot tub and a sauna. More

From US$ 644 Book Now

Ibis By Avantstay Close To Duval Street W Shared Pool Month Long Stays Only

714 Olivia #11, Key West, United States View map

This Key West villa is a mere 1.1 km from Ripley's Believe It or Not Museum and walking distance from The Ernest Hemingway Home and Museum. The accommodation comes with 1 bedroom and a kitchen with a… More

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Aquaria House -Pool & Boat Dock

Shoreline Road 14, Key West, United States View map

The 4-bedroom Smooth Sailing Villa is situated within 7 km of Key West Firehouse Museum in Key West and offers accommodation with a kitchen. It includes Wi Fi throughout the property along with… More

From US$ 1318 Book Now

Ocean Hideaway On The Atlantic

1800 Atlantic Blvd Suite A206, Key West, United States View map

### Ocean Hideaway On The Atlantic - Your Coastal Retreat Nestled just minutes away from the stunning shores of Smathers Beach, Ocean Hideaway On The Atlantic is a serene and luxurious getaway for… More

From US$ 738 Book Now

Julia Whitehead Guest Suites

1011 Whitehead St Master, Key West, United States View map

Julia Whitehead Guest Suites is situated in Key West, at 450 metres from Duval Street and merely 0.6 km from South Beach. The 3-bedroom villa also comes with a kitchen complete with a microwave oven,… More

From US$ 458 Book Now

Abaco - Large Waterfront 2X2 End Unit With Boat Slip

915 Eisenhower Drive, Key West, United States View map

**Abaco - Large Waterfront 2X2 End Unit With Boat Slip Villa** offers a charming blend of luxury and convenience, ideally situated just 5 kilometers from the vibrant Key West International Airport. More

From US$ 383 Book Now

The Geiger Suite At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

At The Geiger Suite At Inn On Fleming Key West! villa, guests can enjoy windsurfing, snorkelling, and fishing as well as a location 700 metres from the Key West Cemetery. More

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Breezy Retreat

606 Truman Avenue, Key West, United States View map

The 2-bedroom Breezy Retreat Villa Key West is located just 1.5 km from Key West First Legal Rum Distillery and provides a swimming pool, ensuring a relaxing stay. More

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