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2026-06-29
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Holiday Homes in Florida Keys

Sugarloaf Key Rv Resort & Cottages

3000 Johnson Road, Summerland Key, United States Show map

Situated approximately 25 minutes' walk from the Bow Channel, Sugarloaf Key Rv Resort & Cottages Summerland Key invites guests to relax at a patio. Guests can enjoy canoeing and fishing at this… More

From US$ 359 Book Now

Tropical Cottages

243 61St Street Gulf, Marathon, United States Show map

Situated 4.6 km from the snug Sunset Park Beach, the family-managed Tropical Cottages Marathon entices guests to explore various tourist attractions in the area. More

From US$ 83 Book Now

Tree Top Paradise

701 Spanish Main Drive 179, Cudjoe Key, United States Show map

Located only 13 minutes' stroll from Gopher Key, the 2-bedroom Tree Top Paradise Cudjoe Key villa offers a terrace with views of the pool. Offering a private swimming pool, the Cudjoe Key holiday… More

From US$ 237 Book Now

Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking

Seaside Drive 3625, Key West, United States Show map

Situated about a 25-minute stroll from the Smathers Beach, Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking Key West villa entices guests to enjoy cycling and fishing in… More

From US$ 595 Book Now

Truman @ Duval

Key West, United States Show map

Situated approximately a 5-minute stroll from the Key West Lighthouse and Keeper's Quarters Museum, Truman @ Duval Key West villa offers quick access to numerous city landmarks nearby. More

From US$ 210 Book Now

Sea Breeze -Great Location!

Whitehead Street 1025, Key West, United States Show map

Situated about 5 minutes' walk from the Ernest Hemingway Home and Museum, the 1-bedroom Sea Breeze -Great Location! Villa Key West ensures a great leisure experience by offering cycling. Boasting… More

From US$ 536 Book Now

Amelia House

Key West Florida 33040, Key West, United States Show map

Amelia House Villa Key West offers easy access to such tourist spots as the Key West Butterfly and Nature Conservatory, located merely 5 minutes' walk away. More

From US$ 270 Book Now

Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo

915 Eisenhower Drive, Key West, United States Show map

Located a 6-minute walk from the Historic Charter Boat Row, Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo Key West villa offers a patio with a view over the sea. Providing guests… More

From US$ 184 Book Now

Hideaway #23

Key Largo, United States Show map

The 3-bedroom Hideaway #23 Villa Key Largo is located in the immediate vicinity of Dolphins Plus Key Largo and provides a private swimming pool, ensuring a relaxing stay. More

From US$ 1613 Book Now

The Barbados -Bright Condo W Pool

Seaside Drive 3625, Key West, United States Show map

Staying at The Barbados -Bright Condo W Pool Key West villa, guests can easily reach the Bayview Park, located approximately a 10-minute drive away. More

From US$ 282 Book Now

Leeward Isle

Key West, United States Show map

Leeward Isle Villa Key West offers proximity to nearby tourist spots, such as the even Southernmost Point, situated 11 minutes' walk away. More

From US$ 423 Book Now

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

Duval Street 1075, Key West, United States Show map

Located a mere 1.3 km from the natural history museum "Florida Keys Eco-Discovery Center", the 3-bedroom New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool Key West offers a patio with views… More

From US$ 343 Book Now

Starfish Seas Key Largo Ocean Pointe 1302

Burton Drive 500, Key Largo, United States Show map

The 2-bedroom Starfish Seas Key Largo Ocean Pointe 1302 Villa is located within easy reach of the Hammer Point and offers guests to relish a patio as well as an outdoor swimming pool. Offering Wi-Fi,… More

From US$ 452 Book Now

Home On The Water In Marathon, Fl

1301 Grouper Drive, Marathon, United States Show map

Located 5 km from The Turtle Hospital, Home On The Water In Marathon, Fl provides access to various tourist attractions in the vicinity. More

Book Now

The Exuma Cay -Pool View & Parking

Seaside Drive 3625, Key West, United States Show map

Situated 4.7 km from the Key West Butterfly and Nature Conservatory, The Exuma Cay -Pool View & Parking Villa Key West provides access to numerous tourist attractions in the area. More

From US$ 579 Book Now

Vacay Vibes At Mariners Club- Luxury Home In Oceanfront Resort With Pools, Pickleball & Marina

97501 Overseas Highway 604, Key Largo, United States Show map

Situated around a 5-minute walk from the American Outdoors, the 4-bedroom Vacay Vibes At Mariners Club- Luxury Home In Oceanfront Resort With Pools, Pickleball & Marina Key Largo is ideal for up to… More

From US$ 577 Book Now

Sky Loft In Key West

Southard Street 611, Key West, United States Show map

Situated in the Downtown Key West district, an 11-minute stroll from the Key West Butterfly and Nature Conservatory, Sky Loft In Key West Villa comes with an outdoor swimming pool for guests to… More

From US$ 512 Book Now

The Butterfly Cottage - Certified Butterfly Sanctuary - Ocean View Hot Tub - Authentic Keys Charm

443 97Th Street, Marathon, United States Show map

The 2-bedroom The Butterfly Cottage - Certified Butterfly Sanctuary - Ocean View Hot Tub - Authentic Keys Charm Marathon is located merely 1.9 km from the Florida Keys Aquarium Encounters and… More

From US$ 349 Book Now

Tiny Home On Waterfront, Bay Views, Deck, Pool

999 Morris Avenue, Jewfish, United States Show map

The 1-bedroom Tiny Home On Waterfront, Bay Views, Deck, Pool Jewfish offers proximity to nearby tourist spots, such as the Little Blackwater Sound, situated 2.8 km away. More

Book Now

Casa Blue Pelican.

11545 2Nd Avenue Ocean, Marathon, United States Show map

The 2-bedroom Casa Blue Pelican. Marathon is located nearly 15 minutes' walk from the EAA Air Museum and offers guests to enjoy their evening on a patio with a dining table. The property is situated… More

From US$ 510 Book Now

The Trinidad -Pool & Parking

Seaside Drive 3625, Key West, United States Show map

Located within 25 minutes' walk of Sheriff s Animal Farm, The Trinidad -Pool & Parking Villa Key West provides access to various tourist attractions in the vicinity. More

From US$ 336 Book Now

Southernmost Sanctuary

1330 Simonton Street, Key West, United States Show map

Located nearly a 25-minute walk from the waterfront Mallory Square, the 6-room Southernmost Sanctuary Villa Key West provides access to various tourist attractions in the vicinity. More

From US$ 118 Book Now

The Andros -4Th Floor Sunset View

Seaside Drive 3625, Key West, United States Show map

The Andros -4Th Floor Sunset View Villa Key West offers proximity to nearby tourist spots, such as the waterfront Mallory Square, situated about 6 km away. More

From US$ 491 Book Now

Kw44 Conch Casa

Key West, United States Show map

Staying at Conch Casa Villa Key West, guests can visit the Ernest Hemingway Home and Museum, which is only 300 metres away. Located in the Downtown Key West district, the Key West holiday home offers… More

From US$ 614 Book Now

Blue Ocean Bungalow

538 27Th Street Ocean, Marathon, United States Show map

At the 3-bedroom Blue Ocean Bungalow Marathon, guests can enjoy canoeing and fishing as well as a location nearly a 5-minute walk from The Turtle Hospital. More

From US$ 329 Book Now

Kw24 Key Lime Calypso

409 Petronia Ave, Key West, United States Show map

Offering a location 17 minutes' walk from the Fort Zachary Taylor, Key Lime Calypso Villa Key West gives access to various tourist spots in the area. More

From US$ 333 Book Now

Pelican'S Roost, Waterfront Comfort At Venture Out

701 Spanish Main Drive Unit 454, Cudjoe Key, United States Show map

Located only 1.5 km from the American Shoal Lighthouse, Pelican'S Roost, Waterfront Comfort At Venture Out Cudjoe Key villa features a swimming pool, a Jacuzzi, ensuring a relaxing stay. Featuring a… More

From US$ 405 Book Now

Full Time Lic Mgr - Luxurious 3 Bed 3 Bath Oceanfront Suite - Upscale Oceanfront Resort - Indoor Pickleball - Speakeasy!

97501 Overseas Highway Suite 524, Key Largo, United States Show map

Located within 5 minutes' walk of the American Outdoors, the 3-bedroom Lic Mgr - Luxurious 3 Bed 3 Bath Oceanfront Suite - Upscale Oceanfront Resort - Indoor Pickleball - Speakeasy! Key Largo villa… More

From US$ 798 Book Now

Beach House Getaway - 2Br 2-5Ba Coastal Villa

5097 Sunset Village Drive, Duck Key, United States Show map

Located merely a 5-minute walk from the Hawks Cay Boulevard, Beach House Getaway - 2Br 2-5Ba Coastal Villa Duck Key offers a terrace with a view over the sea. More

From US$ 567 Book Now

St Croix - Downtown 4X4 Waterfront Penthouse Pool Dock Pet

915 Eisenhower Drive, Key West, United States Show map

The 4-bedroom St Croix - Downtown 4X4 Waterfront Penthouse Pool Dock Pet Villa Key West offers quick access to such tourist spots as the Wreckers Sloop Mary, situated just a 5-minute walk away. More

From US$ 1966 Book Now

Just Steps To Duval- Sleeps 10- Heated Pool House

Truman Avenue 417, Key West, United States Show map

The 3-bedroom Just Steps To Duval- Sleeps 10- Heated Pool House Villa Key West offers proximity to such city sites as the historic Key West Lighthouse, located just a 5-minute walk away. More

From US$ 1183 Book Now

Reef House

5070 Sunset Village Dr Unit C103, Duck Key, United States Show map

Reef House Villa Duck Key is located 2.7 km from the Keys Cable Park, giving access to various tourist spots nearby. More

From US$ 461 Book Now

Newly Renovated And Cozy Home In The Florida Keys

11105 1St Avenue Ocean, Marathon, United States Show map

The 2-bedroom Newly Renovated And Cozy Home In The Florida Keys Marathon is located only 8 minutes' walk from the Florida Keys Aquarium Encounters and features a swimming pool as well as a terrace… More

From US$ 253 Book Now

Papaya Place By Avantstay

110A 1800 Atlantic Blvd, Key West, United States Show map

The 0-bedroom Papaya Place By Avantstay Key West villa, located merely a 5-minute stroll from The Key West Nature Preserve, entices guests with a swimming pool as well as a hot tub to relax in. More

From US$ 556 Book Now

Frost Free In Cayo Hueso

1800 Atlantic Blvd Unit C439, Key West, United States Show map

Located only 0.8 km from the Higgs Beach Dog Park, the 2-bedroom Frost Free In Cayo Hueso Villa offers a swimming pool for guests to relax by. Featuring a sauna, the holiday home is around 10 minutes… More

From US$ 674 Book Now

Ta15 Ocean Pointe #2210

Tavernier, United States Show map

Situated in close proximity to the Florida Keys Wild Bird Rehabilitation Center, Coastal Retreat With Private Balcony, Pool, & Easy Beach Access Tavernier villa ensures a great leisure experience by… More

From US$ 187 Book Now

Aruba - Downtown Waterfront 2X2 Dock & Pool Pet-Friendly

915 Eisenhower Drive, Key West, United States Show map

The 2-bedroom Aruba - Downtown Waterfront 2X2 Dock & Pool Pet-Friendly Villa Key West is located nearly a 5-minute walk from the Bayview Park and offers guests to relish a patio as well as an outdoor… More

From US$ 1144 Book Now

New The Cottage At James House

512 Caroline Street, Key West, United States Show map

Located just an 8-minute stroll from the vintage parish "Saint Paul's Episcopal Church of Key West", the 1-bedroom New The Cottage At James House Key West includes a patio with views of the city. More

From US$ 519 Book Now

Paradise At Sunset

5 Kyle Way East, Marathon, United States Show map

Paradise At Sunset Marathon villa provides easy access to various city attractions, such as Knight's Key, situated about a 5-minute walk away. More

From US$ 577 Book Now

Dk18 Duck Key Retreat Villa #5105

5105 Sunset Village Dr., Duck Key, United States Show map

Duck Key Retreat Villa #5105 offers quick access to such tourist spots as the Hawks Cay Boulevard, situated a mere 5 minutes' walk away. Guests can enjoy fishing at the accommodation, located 3.2 km… More

From US$ 201 Book Now

Sea View And Sunrise Top Floor Ocean Pointe 2412

Burton Drive 500, Key Largo, United States Show map

The 2-bedroom Sea View And Sunrise Top Floor Ocean Pointe 2412 Key Largo villa is situated in close proximity to the Hammer Point, featuring such comforts as Wi-Fi and parking. More

From US$ 645 Book Now

St Kitts - Downtown Waterfront Penthouse Pool Dock Parking

915 Eisenhower Drive, Key West, United States Show map

Situated within 5 minutes' walk of the Wreckers Sloop Mary, the 4-bedroom St Kitts - Downtown Waterfront Penthouse Pool Dock Parking Villa Key West offers quick access to numerous city landmarks… More

From US$ 547 Book Now

Lazy Daze Double King Suite Ocean Pointe 2310

Burton Drive 500, Key Largo, United States Show map

Offering a patio overlooking the sea, Lazy Daze Double King Suite Ocean Pointe 2310 Key Largo villa is located just near the Hammer Point. Providing guests with Wi-Fi and a car park, the 2-bedroom… More

From US$ 380 Book Now

Ocean Pointe 2309

500 Burton Drive 2309, Tavernier, United States Show map

Located in the immediate vicinity of Old Settler's Park, the 2-bedroom Ocean Pointe 2309 Villa Tavernier offers quick access to various city attractions in the vicinity. More

From US$ 430 Book Now

Coconut House

Duck Key, United States Show map

Coconut House Villa Duck Key offers quick access to such city attractions as the Hawks Cay Boulevard, located approximately a 5-minute walk away. More

From US$ 205 Book Now

Full Time Lic Mgr - Modern 4 Bed 4 Bath Villa - Upscale Oceanfront Resort - Indoor Pickleball - Speakeasy!

97501 Overseas Highway, Key Largo, United States Show map

Offering a swimming pool, Lic Mgr - Modern 4 Bed 4 Bath Villa - Upscale Oceanfront Resort - Indoor Pickleball - Speakeasy! Key Largo is located just 250 metres from the American Outdoors and is ideal… More

From US$ 525 Book Now

Crawl To Duval W/ Hot Tub

415 Truman Avenue, Key West, United States Show map

The 1-bedroom Crawl To Duval W/ Hot Tub Villa Key West is located merely 5 minutes' walk from the Ernest Hemingway Home and Museum and offers a Jacuzzi, ensuring guests a relaxing stay. Situated in… More

From US$ 1642 Book Now

Aqua Vista Ocean Pointe 3307

Burton Drive 500, Key Largo, United States Show map

Situated near the Hammer Point, Aqua Vista Ocean Pointe 3307 Villa Key Largo invites guests to relax at a patio. More

From US$ 416 Book Now

Lavender Jungle By Avantstay

104 Southard Street #1, Key West, United States Show map

Nestled only an 8-minute walk from the Harry S. Truman Little White House, the 0-bedroom Lavender Jungle By Avantstay Key West villa features a swimming pool along with a patio to help guests unwind.… More

From US$ 425 Book Now

Key Largo Sunrise Resort Style Ocean Pointe 5315

Burton Drive 500, Key Largo, United States Show map

Key Largo Sunrise Resort Style Ocean Pointe 5315 villa offers proximity to nearby tourist spots, such as B&B Tavernier Cinema 5, situated 2.5 km away. More

From US$ 515 Book Now