
House holiday rentals in Key West
Find and book unique houses on Airbnb
Quick stats about house rentals in Key West

Total holiday rentals
Explore 510 holiday rentals in Key West

Nightly prices starting at
Key West holiday rentals start at $102 NZD per night before taxes and fees

Verified guest reviews
Over 11,360 verified reviews to help you choose

Family-friendly holiday rentals
440 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 270 rentals that welcome pets

Holiday rentals with a pool
370 properties feature pools

Rentals with dedicated workspaces
260 properties have a dedicated workspace

Wi-Fi availability
500 of Key West holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Key West rentals

4.9 Average rating
Key West stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated house rentals in Key West
Guests agree: These houses are highly rated for location, cleanliness and more.

Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
Historic Harrison's Hideaway is in an 1880's Cigar Maker's cottage renovated in 2010. It features a K size Pottery Barn memory foam bed, custom made full sleeper sofa, renovated kitchen with granite counter tops, 2 burner stove, under counter fridge/freezer, dishwasher, microwave, air fryer/oven tumbled marble 2 person shower, private front deck with seating for 4, 2 person Solana spa. Perfect for a couple or a family with children. Freshly painted a Caribbean blue with plantation shutters.
FamilyValueCleanliness

Captain’s Quarters Ahoy Mateys! Florida, Keys
This is located at the Florida Keys in Key Colony, Marathon. It is a spacious two bedroom, two bathroom duplex surrounded by water. It is a renovated beauty and close to the best restaurants and the tranquility of this city. It is the perfect getaway where you can recharge your exhausted batteries. Captain’s Quarters is a clean and spacious base camp location for the many adventures that await you in this amazing location. Water views and the accessibility to the best fishing in the world.
ValueLocationAmenities

Near Duval: Hot Tub, Sleeps 6, Top Location
Just 30 seconds from vibrant Duval Street, this iconic conch home is your perfect Key West escape! With two bedrooms, one bathroom, a full kitchen, and private outdoor perks—like a hot tub, second-story sundeck, and outdoor shower—you’ll have everything you need to relax in paradise. Ideal for up to 6 guests, it’s a tropical haven steps from world-class dining, shopping, and beaches. Book now and soak up the island life! Don’t forget to click the ♥ to save it for later.
LocationFamilyIndoor spaces

3 Bedroom Home - Perfect Location & Private Pool
The historic William Skelton Home is ideally located on Eaton Street in Old Town Key West, steps from Duval Street and all major attractions. This rental listing includes the second and third floors of the home, which features three bedrooms, a private swimming pool, spacious living areas inside and outside, off-street parking, and a newly renovated chef's kitchen to prepare meals. The first story of the home will be left vacant when this listing is rented.
LocationValueLayout

Private Pool Tropical Oasis - Centrally Located
Centrally located in the Florida keys, this beautiful three-bedroom home is steps away from fishing, restaurants, boat rentals and water sports. The property features a private and lush backyard filled with your own private pool, loungers and outdoor games. In the evening, unwind with a refreshing drink under the outdoor lighting or in the heated pool. The villa includes a high chair, pack and play, bed rails, booster seat, baby gate and kids dishware.
FamilyLocationSleep quality

Waterfront Anchor House with Boat Basin & Ramp!
Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with boat basin and ramp for your boat. The property lot is almost an acre with another rental home and still very spacious (search for Haven House to reserve both homes if available). Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the point and enjoy the underwater scenery!
LocationValueComfort

*Emerald Seas*-Florida Keys Ocean Front Paradise!
Welcome to our Florida Keys Ocean Paradise, Emerald Seas! Truly a special place to get away and relax. Enjoy the crystal-clear waters and amazing views. Bring or rent a boat, look for sea turtles, manatees, dolphins, lobster & tropical fish right from your patio or dock. Take in a glorious sunrise or moonlit night over the water. The amazing, 180 degree panoramic ocean views will take your breath away every moment you are there.
LocationValueWalkability

Coco Plum Waterfront Hideaway Home in Marathon
This Coco Plum home is the ultimate family getaway! With four bedrooms, two bathrooms, a modern living room with a 4K TV and surround sound, and an outdoor area that includes a fire pit, outdoor dining, and outdoor living space. The boat dock and breathtaking sunset views make this the perfect home for your fishing adventures. Beautiful Coco Plum beach is just a ten minute walk away. Make this home your next island adventure.
FamilyValueAccuracy

NEW! Private Pool, 50’ Dock, Kayaks, Waterfront
Slack Tide Cove Welcome to Slack Tide Cove, a stunning 3-bedroom, 2-bathroom waterfront retreat in the heart of Marathon, FL. This brand-new construction is chicly decorated with a coastal theme, offering the perfect blend of luxury and relaxation. Take in breathtaking views of Boot Key Harbor from the pool or balcony, and enjoy 50 feet of deep-water dockage with a fish cleaning station for your day’s catch.
LocationFamilyDecor

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.
LocationFamilyAmenities

Oceanfront, beach, heated pool, dock, tiki hut
This is a minimum 28 night minimum rental. Welcome to your dream getaway, just 13 miles from downtown Key West! This charming two-level beach home offers the perfect blend of relaxation, adventure, and luxury. With accommodations for up to 10 guests, bring the entire family, friends, and even your fur babies, and don’t forget your boat!
FamilyLocationBiking

Marathon one-level home on the Marina - with slip!
***New Listing! Recently renovated with all new furnishings and appliances*** Beautiful oasis in the heart of the Florida Keys, Marathon is a fisherman's paradise. Coral Lagoon is the perfect destination for a relaxing family getaway and this home is all new with stylish interior and unbeatable location.
LocationFamilyWi-Fi
Popular amenities for Key West house rentals
House rentals with a pool

Waterfront 2-bedroom Home w/Pool and Spa
LocationFamilyBreakfast

Palm - Beach Houses Key West
LocationValueBathroom

Ocean~View w/ Dock, Pool, Kayaks, King Bed
FamilyValuePool

Luxury Boating Paradise+Pool+Sailing Kayaks
LocationFamilyCleanliness

Grand Sands/120'Dock/Mini Golf/HtdPool /Game Room
ValueLocationWalkability

Funky Chicken Cottage with Shared Pool in Paradise
FamilyLocationPool

Palm Breezes! Room for Everyone on the Ocean.
ValueLocationAccess

Angler’s Terrace Conde Nast Traveler’s Best Airbnb
ValueLocationQuiet
Weekly house rentals

Key West Paradise
ValueLocationDecor

Off The Charts-Waterfront Tiki Bar & Private Dock
FamilyLocationIndoor spaces

3/2 Home w Dock, lagoon, kayaks!
FamilyLocationComfort

Flamingo Palms-April availability
FamilyLocationSleep quality

Waterfront Oasis3/2 Direct Ocean
FamilyLocationSleep quality

Tiki Time in Cudjoe Key 136
FamilyLocationView

Private Pool Oasis | 3 King Suites | 30 Min to KW
LocationFamilyShared spaces

Viamarhe House-Private beach, Kayak, yard games
FamilyValueGetting around
Private house rentals

Florida Keys Oceanside Utopia
ValueFamilyCleanliness

Villa 7218 on Duck key - Boat Slip Available
FamilyLocationNearby

Waterfront House - 30' Dock & Pool at Cabana Club
LocationFamilyCleanliness

Mermaid's Paradise ~ Pool ~ Dock ~ Games ~ Views!
ValueFamilyView

Beautiful Beachfront Villa w/ Pool/Tiki/Dock
FamilyLocationCondition

Waterfront Private Home w/Pool-Family&Pet Friendly
FamilyValueCleanliness

KeyColony,4 Bedroom, Pool, 40'Dock, Quick Vaca Cut
LocationFamilyAmenities

Refuge on the Reef~ Waterfront Pool Home, 75' Dock
ValueLocationAccess
When is the best time to visit Key West?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $942 NZD | $1,123 NZD | $978 NZD | $759 NZD | $669 NZD | $624 NZD | $605 NZD | $579 NZD | $524 NZD | $624 NZD | $712 NZD | $807 NZD |
| Avg. temp | 21°C | 22°C | 24°C | 25°C | 27°C | 29°C | 30°C | 30°C | 29°C | 27°C | 25°C | 23°C |
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
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- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
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- Tampa Bay Holiday rentals
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- Sombrero Beach
- Smathers Beach
- Long Beach
- Bahia Honda State Park
- Sunset Park
- Ernest Hemingway Home & Museum
- Fort Zachary Taylor Historic State Park
- Seven Mile Bridge
- The Turtle Hospital
- Florida Keys Aquarium Encounters
- Key West Lighthouse Museum
- Southernmost Point
- Key West Butterfly & Nature Conservatory
- Boyd's Key West Campground
- Calusa Beach & Loggerhead Beach
- Boca Grande Key
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