Special offers and Exclusive deals

Search Hotels

2026-05-13
2026-05-14
Guests

Filter Results

Hotels by class

Hotel name

Price per night

Accommodation type

Districts

Attractions

Thematic hotels

Review rating

Hotel facilities

Room facilities

Apply Filters
Clear Filters

Key West holiday rentals

Alligator Reef Light Suite

419 Truman Avenue #1 F, Key West, United States View map

The 1-bedroom Alligator Reef Light Suite Key West villa provides easy access to various city attractions, such as the downtown commercial zoned Duval Street, situated nearly 5 minutes' walk away. More

Book Now

American Shoal Light Suite

419 Truman Avenue, Key West, United States View map

The 1-bedroom American Shoal Light Suite Key West villa provides easy access to various city attractions, such as Key West Lighthouse and Keeper's Quarters Museum, situated approximately 5 minutes'… More

Book Now

Villa The Watson House

525 Simonton Street, Key West, United States View map

Along with proximity to Key West First Legal Rum Distillery, just 650 metres away, the 4-bedroom Villa The Watson House Key West offers opportunities for windsurfing, snorkelling, and canoeing in the… More

Book Now

Aria At Azul Mansion Key West

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

More

From US$ 889 Book Now

Sombrero Reef Light Suite

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

The 1-bedroom Sombrero Reef Light Suite Key West villa offers swift access to various city sites, such as Key West Lighthouse and Keeper's Quarters Museum, situated nearly 5 minutes' walk away. More

From US$ 429 Book Now

Flaglers Oasis By Avantstay

2209 Flagler Ave Is #B, Key West, United States View map

Guests can enjoy a seaside sea view from a terrace at the welcoming Flaglers Oasis By Avantstay Key West villa, 3 km from the Ripley's Believe It or Not. More

From US$ 181 Book Now

The Mallory Suite At Inn On Fleming Key West!

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

Along with proximity to the 19 - acre Key West Cemetery, just a 9-minute walk away, The Mallory Suite At Inn On Fleming Key West! villa offers opportunities for windsurfing, snorkelling, and fishing… More

From US$ 441 Book Now

Egret Suite - Southernmost Sanctuary

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

Situated just 5 minutes' stroll from the even Southernmost Point, the 1-bedroom Egret Suite - Southernmost Sanctuary Key West villa offers quick access to numerous city landmarks nearby. More

From US$ 354 Book Now

Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom

915 Eisenhower Drive, Key West, United States View map

The 2-bedroom Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom Key West villa is located around 5 minutes' walk from Wreckers Sloop Mary and offers guests to relish a patio as well as a… More

From US$ 776 Book Now

St John - Downtown Waterfront Penthouse Pool Parking Dock

915 Eisenhower Drive, Key West, United States View map

The 4-bedroom St John - Downtown Waterfront Penthouse Pool Parking Dock Villa Key West is located only 6 minutes' walk from the C. B. Harvey Rest Beach Park and offers guests to relish a patio as… More

From US$ 2344 Book Now

Petes West Cottage

505 Louisa Street, Key West, United States View map

The 1-bedroom Petes West Cottage Key West is located approximately a 15-minute walk from Memorial Sculpture Garden and welcomes its guests to enjoy windsurfing, snorkelling, and canoeing. More

Book Now

Villa Angelita By Last Key Realty

421 Angela Street Unit B, Key West, United States View map

The 2-bedroom Villa Angelita By Last Key Realty Key West provides easy access to various city attractions, such as Duval Street, situated around 5 minutes' walk away. More

From US$ 957 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

Fleming-O

726 Fleming St, Key West, United States View map

Staying at the 1-bedroom Fleming-O Villa Key West, guests can visit Higgs Beach Dog Park, which is nearly a 25-minute walk away. This Key West holiday home is located in the Downtown Key West… More

Book Now

Casita Angelita By Last Key Realty

421 Angela Street Unit A, Key West, United States View map

Staying at the 2-bedroom Casita Angelita By Last Key Realty Key West villa, guests can easily reach Key West Wildlife Center, located around 25 minutes' walk away. More

From US$ 750 Book Now

Sandpiper On The Ocean

1800 Atlantic Blvd C420, Key West, United States View map

To enjoy your vacation in Key West, stay at the 2-room Sandpiper On The Ocean Apartment Key West, which is within a 3-km distance of Fort Zachary Taylor and around a 25-minute stroll from Key West… More

From US$ 695 Book Now

Sundial On The Atlantic Ocean View

1800 Atlantic Blvd, Unit C328, Key West, United States View map

**Sundial On The Atlantic Ocean View is an idyllic retreat where luxury meets the vibrant spirit of Key West. Just 5 kilometers from Key West International, this stunning oceanfront haven offers… More

From US$ 561 Book Now

Harbor House Penthouse- B

423 Front Street, Key West, United States View map

More

Book Now

Brisa Del Mar By Avantstay

1901 S.Roosevelt Blvd 206E, Key West, United States View map

The welcoming Brisa Del Mar By Avantstay Key West villa is located a 10-minute drive from the Key West Firehouse Museum and provides a swimming pool, ensuring a relaxing stay. More

From US$ 615 Book Now

New The Windrose House - Pool & Pets

Shoreline Road 3, Key West, United States View map

The 6-bedroom New Windrose House By Brightwild - Pool & Pets Villa is at a 7 km distance from Key West Firehouse Museum and it takes 10 minutes to drive to Key West International airport. The… More

From US$ 2971 Book Now

New Private Pool & Docking - Floralee House

Mangrove Lane 11, Key West, United States View map

**Discover the Charm of New Private Pool & Docking - Floralee House Villa Key West** Nestled in the enchanting surroundings of Key West, New Private Pool & Docking - Floralee House invites you to… More

Book Now

Always Your Paradise By Avantstay

620 Thomas Street #164, Key West, United States View map

Situated only 450 metres from the downtown commercial zoned Duval Street, the 1-bedroom Always Your Paradise By Avantstay Key West villa has a swimming pool with a patio. Featuring access to a patio,… More

Book Now

Pelican Suite - Southernmost Sanctuary

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

Located nearly 5 minutes' walk from Dog Beach, the 1-bedroom Pelican Suite - Southernmost Sanctuary Key West villa offers quick access to various city attractions in the vicinity. More

From US$ 483 Book Now

The Mesa House-Close To Duval!

Simonton Street 220, Key West, United States View map

The 3-bedroom Mesa House Villa is nearly 8 minutes on foot from Truman Little White House and walking distance from the bustling plaza "Mallory Square". A fully furnished kitchen with a microwave… More

From US$ 1379 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

The Elizabeth Suite

1501 Truman Avenue 1, Key West, United States View map

Situated just a 5-minute stroll from The Unitarian Universalist Fellowship of Key West, the 1-bedroom The Elizabeth Suite Key West villa offers easy access to numerous tourist spots in the area. More

From US$ 383 Book Now

Brand New Catchlight House With Private Pool

Mangrove Lane 7, Key West, United States View map

The 7-bedroom Brand New Catchlight House With Private Pool Villa Key West is located around a 25-minute walk from Key West Tropical Forest and Botanical Garden and provides fishing for active guests. More

Book Now

The Fleming Suite

1501 Truman Avenue 3, Key West, United States View map

Nestled a 20-minute walk from The Ernest Hemingway Home and Museum, The Fleming Suite Key West villa entices guests to explore various tourist destinations nearby. More

From US$ 357 Book Now

Paradise Place By Avantstay

905 White St #1, Key West, United States View map

Featuring a swimming pool for guests' relaxation, the 1-bedroom Paradise Place By Avantstay Key West villa is located nearly 20 minutes' walk from the Higgs Beach. This welcoming holiday home in… More

From US$ 789 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

Coconut Palm

Whitehead Street 729, Key West, United States View map

**Coconut Palm Villa Key West** invites guests to experience the vibrant ambiance of Duval Street, where island-inspired charm meets contemporary luxury. Nestled amid a lively backdrop, this oasis… More

From US$ 1683 Book Now

Tranquility By Avantstay

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

Located in the Downtown Key West district of Key West, a mere 6 minutes' walk from the Minor Saint Mary Star of the Sea Basilica, the 0-bedroom Tranquility By Avantstay Key West villa offers patio… More

From US$ 448 Book Now

Upper Sunset North

801 Eisenhower Dr. #8, 8, Key West, United States View map

**Experience Laid-Back Luxury at Upper Sunset North Villa Key West** Recreational amenities abound, with a lavish outdoor pool surrounded by lounge chairs and tables for ultimate relaxation. More

From US$ 884 Book Now

Toon Hall Tropical Village

1400 Alberta St #A, Key West, United States View map

Along with proximity to Higgs Beach, a mere 0.6 km away, the 2-bedroom Toon Hall Tropical Village Key West villa offers opportunities for canoeing, hiking, and cycling in the area. More

From US$ 1271 Book Now

Joan'S Caribbean Hideaway

143 Golf Club Drive, Key West, United States View map

Conveniently situated, Joan's Caribbean Hideaway Villa serves as the perfect base for exploring Key West's myriad attractions. More

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

Royal Poinciana Weekly Rental!

620 Thomas Street #292, Key West, United States View map

Royal Poinciana Weekly Rental! Key West villa is located an 8-minute walk from the Ernest Hemingway Home and Museum and offers guests to enjoy snorkelling and fishing. More

Book Now

Julie At Scarlet Mango Inn Key West

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

More

Book Now

Olivia'S Nest

828 White Street #1, Key West, United States View map

Situated only 1.5 km from Nancy Forrester's Secret Garden, Olivia'S Nest Villa Key West entices guests to enjoy windsurfing, snorkelling, and canoeing in the area. More

Book Now

Antigua Suite By Last Key Realty

329 William Street #3, Key West, United States View map

**Discover the Charm of the Antigua Suite by Last Key Realty** More

Book Now

Almost Paradise

106-7 Southard Street, Key West, United States View map

Located 12 minutes' walk from the Curry Mansion, Almost Paradise Key West villa gives access to various tourist sites in the vicinity. More

Book Now

Golf Course Oasis W/ Private Yard, 5 Mi To Duval!

28 Merganser Ln, Key West, United States View map

The 2-bedroom Golf Course Oasis With Private Yard, 5 Mi To Duval! Villa Key West offers proximity to nearby tourist spots, such as the Smathers Beach, situated around 10 minutes' drive away. More

Book Now

Honey At Scarlet Mango Inn Key West

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

More

Book Now

A Sunset View

104-5 Southard Street, Key West, United States View map

Staying at A Sunset View Villa Key West, guests can visit the 19 - acre Key West Cemetery, which is only 14 minutes' walk away. More

Book Now

Southern Skies, Stylish Home In Old Town Key West

315 Catherine Street #2, Key West, United States View map

Featuring a private swimming pool for guests' enjoyment, Southern Skies, Stylish Home In Old Town Key West is nestled in the centre of Key West, 1.2 km from Nancy Forrester's Secret Garden. More

Book Now

Bahamian Reed By Avantstay

510 Porter Lane, Key West, United States View map

The welcoming Bahamian Reed By Avantstay Key West villa provides easy access to various city attractions, such as the US 1 Mile Marker 0, situated nearly 5 minutes' walk away. More

From US$ 434 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

Island Oasis

101 Front Street, #25, Key West, United States View map

Situated merely 7 minutes' stroll from the Key West Aquarium, Island Oasis Villa Key West offers quick access to numerous city landmarks nearby. More

Book Now

About Time

620 Thomas Street Apt# 193, Key West, United States View map

About Time Villa Key West is located a mere 10 minutes' walk from the Harry S. Truman Little White House, giving access to various tourist spots nearby. More

Book Now

Waterfront Key West Oasis W/ Float Dock!

31 Palm Dr, Key West, United States View map

Guests can enjoy a seaside sea view from a terrace at Waterfront Key West Oasis With Float Dock! Villa, just a few steps from the Lower Sugarloaf Sound. More

Book Now