Airbnb your place

Holiday rentals in Key West

Find and book unique accommodation on Airbnb

Quick stats about holiday rentals in Key West

  • Total holiday rentals

    Explore 2,110 holiday rentals in Key West

  • Nightly prices starting at

    Key West holiday rentals start at $13 SGD per night before taxes and fees

  • Verified guest reviews

    Over 74,900 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,250 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 730 rentals that welcome pets

  • Holiday rentals with a pool

    1,650 properties feature pools

  • Rentals with dedicated workspaces

    1,010 properties have a dedicated workspace

  • Wifi availability

    2,050 of Key West holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Self check-in, Free parking on premises and Monthly stays across Key West rentals

  • 4.8 Average rating

    Key West stays are highly rated by guests – averaging 4.8 out of 5!

Top-rated holiday rentals in Key West

Guests agree: these stays are highly rated for location, cleanliness and more.

1 of 1 pages1 / 1
Guest favourite
Boat in Key West

3BR In Resort Village, Pools, Free Kayak & Shuttle

Experience the ultimate KEY WEST VIBE aboard our 3BR/2BA sailboat Located at the luxury Perry Hotel, you’ll enjoy on water living, palm trees, and salty air. Free Perks: Kayak, pools, parking, & free shuttle to Old Town! Full Resort Access: 2 pools & hammock park, 3 restaurants, ice cream shop, private bathhouse & Views of million-dollar yachts Plz read everything below before booking. I want you to be completely informed about staying on the water. We look forward to hosting you! 🌊💙⚓

FamilyLocationSleep quality

4.81 out of 5 average rating, 27 reviews
Guest favourite
A motorboat is anchored on calm waters, featuring a spacious front deck. Two individuals are seated comfortably, enjoying the view. The boat's sleek design is complemented by a canopy overhead and small steps leading into the water, creating a relaxed atmosphere.
Boat in Key West

Stay on Roxie - free transport & snacks, BYOB.

Read our reviews and relax with last minute weather cancellation! 🌞 Shower, toilet and power to recharge phones, full cellular. Enjoy a peaceful night or two on the water! Free parking and one free round trip transport to/from Roxie per night stay! Roxie is anchored in ~3ft lagoon. We live on a boat a half-mile away if you need anything at all! Roxie has a Keurig, coffee pods, bread, peanut butter-jelly, and bottled waters. No cooking but you may bring to-go food, beer/booze/wine. 🛥️🌴🎣

LocationFamilyGetting around

4.9 out of 5 average rating, 245 reviews
Guest favourite
A private conch cottage floats on calm waters, featuring a light green exterior with white trim. Spacious decks are present at the front and back, while paddle boards and kayaks are visible nearby, highlighting the connection to the surrounding nature.
Houseboat in Key West

Key West Outpost: eco-vacation

The Outpost is a unique experience. This is a place where you can be completely off the grid, but still have all of the amenities. Private conch cottage on the backcountry waters surrounding Key West. Enjoy watching the amazing wildlife from your private deck. You can paddle board, kayak or do some light tackle fishing right off the boat. You can even add eco-tours to enhance the adventure. We will take you out for arrival and bring you back on your departure day, via one of our other boats.

FamilyLocationParking

4.95 out of 5 average rating, 84 reviews
Top guest favourite
Aerial view showcasing a waterfront property bordered by vibrant green mangroves. The calm turquoise water reflects the blue sky dotted with white clouds. A marina with docked boats is visible nearby, creating a serene coastal landscape.
Apartment in Key West

Gorgeous Ocean View in Paradise, Close to Key West

This is paradise! Wake up to a gentle breeze and birds singing just outside your balcony. Watch the sunrise over the ocean and mangroves from your private balcony. Enjoy your privacy as you start your day, then venture out to explore all that Key West has to offer: water sports, quaint shops, delicious food, history all around you, and so much more! On property features: Pool, Hot Tub, Yellowfin Bar & Kitchen and Parking. Beach supplies included: Coolers, Snorkel Gear and Beach Towels.

ValueFamilyDecor

4.99 out of 5 average rating, 140 reviews
Guest favourite
Flat in Key West

Designer Waterfront Estate - Lunara Bay Collection

When you book this listing, you’ll be assigned one of our luxury waterfront homes within Lunara Bay, a gated collection of 26 upscale residences in Key West. Each 4+bedroom, 4.5+bath home offers high-end design, amenities, a private pool, marina access, parking, and a pet-friendly gated yard—perfect for your Key West getaway. Enjoy complimentary access to FYT Key West and personalized itineraries from our guest experience team to help you discover local favorites and hidden gems.

LocationFamilyKitchen

4.85 out of 5 average rating, 33 reviews
Guest favourite
Home in Key West

Key West House

Bring the whole family to this great place with lots of room for fun. Walking distance to Smather’s Beach and Higgs Beach. Only 14 minute drive to downtown. Peaceful and relaxed community, immersive local experience. Renting only month to month, bookings of minimum 28 day stay. Please message with any further questions or for more information, would be happy to provide! -Updated bathrooms with rain showers -New furniture -Deep cleaned and sanitized before each stay -Heated pool

LocationFamilyBack garden

4.84 out of 5 average rating, 19 reviews
Guest favourite
A bright and airy living space features a large sectional sofa, a dining area with a light-colored table and chairs, and large glass doors leading to a balcony with water views. Light wood paneling and artwork enhance the overall ambiance.
Apartment in Key West

Waterfront Dock Pool Condo Near Duval St Pet OK

Bring friends and family to this spacious 1,350 sq ft waterfront corner condo in historic downtown Key West. Enjoy a full kitchen, open living space, and a private balcony with marina and pool views. Dockage available with a fish cleaning station and commercial ice maker, perfect for boating and fishing. Located about 1 mile from Duval Street, the Historic Seaport, and Hemingway House. Amenities include a heated pool, tiki area, BBQ grills, parking, elevator, and secure entry.

LocationFamilyParks

4.89 out of 5 average rating, 281 reviews
Superhost
Home in Marathon

Marathon Oceanfront 4BR Private Pool 60’ Boat Dock

Wake up to open-water views at your private oceanfront retreat in Marathon. Bring the boat, step into your private pool, Perfect for families and boating groups.Your private 60' dock offers direct water access, freshwater for rinsing gear and flushing engines, while parking accommodates up to 4 vehicles. • Direct oceanfront setting • Private swimming pool • Private 60' boat dock • Complimentary kayaks • Sleeps up to 10 • Parking for 4 vehicles • Wi-Fi + dedicated workspace

FamilyLocationCleanliness

5.0 out of 5 average rating, 4 reviews
Top guest favourite
Houseboat in Key West

Strictly Pleasure | Unique Yacht Stay in the Keys

Staying aboard Strictly Pleasure offers a truly unique Keys experience. Enjoy life on the water with beautiful marina views, sunsets from the bow, and the charm of staying on a classic yacht. Located at Perry Marina, guests have access to pools, waterfront restaurants, and the trolley to downtown Key West. It’s the perfect mix of relaxation, location, and a one-of-a-kind stay you won’t find in a typical hotel.

FamilyLocationWalkability

5.0 out of 5 average rating, 20 reviews
Top guest favourite
Home in Key West

Pilar House

Charming 3BR/2BA townhouse in the heart of Old Town Key West. Just steps from restaurants, bars, shops, and attractions, yet on a quieter street for a relaxing stay. Two queen bedrooms downstairs, a king master with a balcony upstairs, plus a queen sofa bed to sleep 8. Enjoy a large private deck perfect for morning coffee, lounging, or BBQs. The ideal mix of comfort, space, and unbeatable walkability.

ValueFamilyAccuracy

4.96 out of 5 average rating, 46 reviews
Guest favourite
Boat in Key West

Waterfront Boat Stay + Resort Amenities

Docked at the exclusive Perry Hotel & Marina, this 40-foot, 2-bedroom luxury yacht is tucked away from the crowds, while remaining just minutes from downtown Key West. Featuring inviting indoor and outdoor spaces for living, dining, and relaxing, it offers the perfect balance of comfort and adventure. Guests enjoy hotel amenities, including two pools, a gym, and three waterfront bars and restaurants.

LocationValueCondition

4.94 out of 5 average rating, 35 reviews
Guest favourite
The Tiki Suite is presented on a wooden platform, showcasing thatched roofing and an inviting porch area. Two stand-up paddleboards are placed alongside the structure, with calm waters reflecting the clear sky.
Houseboat in Key West

Tiki Suites ~ Original Tiki ~ Floating Bungalows

Stay on the water in this one-of-a-kind Tiki Suite in Key West. This private floating bungalow blends boat life with comfort, featuring a custom bed, panoramic views, and direct access to the ocean. Swim, paddle, or relax in a hammock surrounded by nature. A peaceful, off-grid glamping experience you won’t find anywhere else. Accessible by boat only.

ValueLocationIndoor spaces

4.91 out of 5 average rating, 561 reviews

Popular amenities for Key West holiday rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Stay near Key West's top sights

Key West

393 locals recommend

Fort Zachary Taylor Historic State Park

1,527 locals recommend

Key West International Airport

11 locals recommend

Smathers Beach

61 locals recommend

Ernest Hemingway Home & Museum

273 locals recommend

Southernmost Point

107 locals recommend

Other great holiday rentals in Key West

Guest favourite
A light-filled living area features a comfortable sofa paired with accent tables. Soft blue walls create a calming backdrop, while stylish decor elements, such as framed artwork and lamps, add character. A mirror reflects the space, enhancing its openness and inviting ambiance.
Apartment in Key West

EYW Getaway

LocationFamilyCleanliness

4.99 out of 5 average rating, 86 reviews
Top guest favourite
Lounge chairs with blue umbrellas surround a sandy beach area, providing a relaxed setting by the water. Steps lead down to the shoreline, where vibrant greenery and palm trees offer a natural frame against the bright blue sky and turquoise sea.
Home in Summerland Key

Ocean front classic keys cottage

FamilyLocationComfort

4.95 out of 5 average rating, 20 reviews
Guest favourite
A light and airy living area features a modern blue sofa adorned with patterned throw pillows. A wooden coffee table sits in front, complemented by a tall indoor plant. A full-length mirror reflects the space, while natural light brightens the room through the patio door.
Flat in Key West

Duval Corner - Pet friendly with Balcony

LocationValueIndoor spaces

4.86 out of 5 average rating, 57 reviews
Superhost
Houseboat in Marathon

Tiny Home Aqua Lodges 2/1

ValueFamilyWifi

4.77 out of 5 average rating, 148 reviewsA comfortable room features a spacious bed with crisp white linens, positioned against a coral-themed accent wall. Natural light streams through a window with white shutters. A small dining table and chairs complement a kitchenette area, while a large mirror enhances the sense of space.
Flat in Key West

At Mine | Lovely Suite steps from Duval Street

FamilyValueComfort

4.86 out of 5 average rating, 1739 reviews
Guest favourite
A floating home is anchored in calm waters, featuring a sleek design with large windows. Two red buoys are visible alongside the vessel. A paddle board rests on the top deck, which is covered for shade, inviting guests to relax while taking in the surrounding nature.
Boat in Key West

“The Easy Way” Comfy, Practical, Convenient

LocationAmenitiesOutdoor spaces

5.0 out of 5 average rating, 24 reviewsA tranquil resort pool is framed by palm trees with lounge chairs positioned along its perimeter. The gentle waves of the Gulf of Mexico are visible in the background, complementing the vibrant sunset sky filled with soft pink and purple hues.
Apartment in Key West

Two Bedroom Residence

FamilyLocationNearby

4.7 out of 5 average rating, 160 reviewsA spacious houseboat floats gracefully on calm waters under a vibrant blue sky. The exterior features a sleek white design with large windows, providing ample natural light. A small dock extends from the side, offering convenient access to the boat.
Houseboat in Key West

Happys Houseboat

ValueLocationCheckout

4.79 out of 5 average rating, 278 reviews

When is the best time to visit Key West?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$570 SGD$661 SGD$614 SGD$513 SGD$434 SGD$387 SGD$373 SGD$340 SGD$313 SGD$386 SGD$438 SGD$489 SGD
Avg. temp21°C22°C24°C25°C27°C29°C30°C30°C29°C27°C25°C23°C

Frequently Asked Questions

  • What are the best places to stay in Key West?

    Key West has inviting neighborhoods like Old Town, known for historic homes, and Mallory Square, which is close to lively waterfront activities. Staying near Duval Street places you close to dining and entertainment, while quieter areas like Truman Annex often attract those seeking a relaxed atmosphere.

  • What are the best things to do in Key West with kids?

    Families often explore the Key West Butterfly and Nature Conservatory, visit the Key West Aquarium, and play on sandy beaches. Interactive museums, pirate-themed tours, and dolphin-watching excursions are frequently suggested for children.

  • What are some of the best things to do in Key West?

    You can explore Ernest Hemingway Home and Museum, stroll lively Duval Street, or watch the sunset at Mallory Square. Visitors frequently snorkel in clear waters, discover art galleries, and tour historic sites around the island.

  • How is the weather in Key West?

    Key West has warm weather year-round, with winter temperatures around 65–76°F (19–24°C) and summer highs reaching 91°F (33°C). Rainfall tends to be higher from June through October, while breezes help make coastal areas pleasant.

  • What are the best places to visit in Key West?

    Mallory Square draws crowds for daily sunset gatherings, and the Southernmost Point is popular for photos. The Ernest Hemingway Home and Museum and Key West Lighthouse highlight the island’s historic character.

  • What are some hiking trails in Key West?

    Key West has shorter walking paths, like the nature trails at Key West Tropical Forest & Botanical Garden and scenic shoreline walks around Fort Zachary Taylor Historic State Park. These areas combine greenery with views of the water.

  • What are some family activities we can do in Key West?

    Families can explore interactive exhibits at the Key West Shipwreck Museum, watch sea life at the Key West Aquarium, or join mangrove kayak tours. Sandy beaches and creative workshops are frequently suggested, especially for children.

  • What are some of the best day trip ideas from Key West?

    Day trips often include exploring the islands and marine life in Dry Tortugas National Park, visiting nearby wildlife refuges, or snorkeling from local boat tours. Historic landmarks and island nature preserves are also frequently suggested.

  • Are there any pet friendly accommodations available in Key West?

    Key West has pet-friendly vacation rentals in several neighborhoods, including Old Town and New Town. Many hosts welcome pets, and local parks make it easy to enjoy island walks with your dog.

  • What are some local tips for visiting Key West?

    Locals recommend wearing reef-safe sunscreen, exploring by bike or foot, and trying fresh seafood at casual spots. Sunset gatherings in Mallory Square and early morning walks along quiet streets offer unique island perspectives.

  • What is Key West known for?

    Key West is known for its lively Duval Street, colorful sunsets, and waterfront celebrations in Mallory Square. The city has a rich literary history, historic architecture, and active arts and water sports communities.

  • What are the best hidden gems to explore in Key West?

    Smaller museums like the Key West Firehouse Museum and Secret Garden, tucked-away art studios, and secluded beaches are frequently suggested by locals. Exploring side streets often reveals tucked-away architecture and murals.

  • What are the best foods to try in Key West?

    Key lime pie is frequently suggested, alongside fresh grouper sandwiches, conch fritters, and tropical fruit salads. Coastal restaurants highlight Caribbean-influenced seafood and Cuban flavors in many dishes.

  • What should I bring for a trip to Key West?

    Pack light clothing, sun protection, swimwear, sturdy sandals, and a reusable water bottle for outdoor activities. A wide-brimmed hat and rain jacket can be useful, especially from late spring through early fall.

  • What is the nightlife in Key West like?

    Duval Street is known for lively bars, music venues, and late-night gatherings, while waterfront lounges around Mallory Square attract sunset crowds. Explore dance floors, drag shows, and laid-back patios throughout the area for varied experiences.

  • What are the most popular events or festivals in Key West?

    Fantasy Fest draws creative costumes and parades each fall, and Hemingway Days celebrates the author's legacy in summer. The Conch Republic Days highlight local history, while waterfront sunset celebrations are daily traditions.

  • Are there family friendly vacation rentals in Key West?

    Key West has family-friendly vacation rentals in neighborhoods such as Old Town, Truman Annex, and Bahama Village. Many hosts provide amenities suitable for children, with easy access to beaches and parks.

  • When is the best time to visit Key West?

    Late winter through spring is often recommended for milder temperatures, less rainfall, and lively events. The island buzzes with festivals, water activities, and vibrant sunsets during these months.

Destinations to explore