Key West Holiday Homes
More than just hotels
Apartments, cabins, holiday rentals and more, plus millions of reviews from Aussie & Kiwi travellers
Flexibility matters
24/7 support, so you can book with confidence
Relax with our Price Promise
Find a lower price on a hotel or package online, before your stay, and we'll refund the difference^
Featured Holiday Homes in Key West

BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!

Key West Dreamin' - Private Pool Steps Off Duval

Perfect Location, Private Heated Pool, Pristine Luxury Home!

**THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES...

HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!

INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!

Key West Caribbean Cottage - On Duval St w Private Pool

LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!

Road's End | Prime Old Town Location! Updated Home w/ Pool

PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!
Holiday Accommodation Key West
You’re the type of person who wants to be right in the middle of it all, but still have your own space. You want to be able to take care of everything yourself, but also get plenty of R&R. Well, holiday rentals in Key West are ready to roll out the welcome mat. We mean that literally—they probably do have a welcome mat. It’s all those little things that will make you fall in love with this type of accommodation, and with Key West itself. Once you’ve stayed in a holiday rental, you’ll wonder why you ever stayed anywhere else.
Key West holiday houses have everything you could need in a place to stay, along with several things you probably never even thought you needed. Towels and linens? Check. Cooking utensils? Check. Dog treats for the pupper? Well, you might want to bring your own to your pet-friendly holiday house, just in case. (He’s a picky little prince anyway, right?) But otherwise you’re good to go. You might even find some games for the little ones, if you’re bringing the family along.
If you are bringing the kids, don’t let that dissuade you from looking for the finer things. Luxury is the name of the game in Key West, and house accommodation is no different. Sure, it should feel like a home away from home—but more like a really fancy home, where you don’t have to worry about cleaning or mowing the lawn. Yes, it’s as great as it sounds.
Make your next getaway truly your own. We’ve got plenty of holiday accommodation in Key West with your name on it, so pack up your favourite books, wine and that playlist of summer hits from 2003. It’s your time to shine.
Key West Holiday Homes essential information
Accommodation | 1043 Holiday Homes |
|---|---|
Lowest Price | NZ$456 |
Highest Price | NZ$4,444 |
Popular accommodation | BAHAMA DREAMING ~ Incredibly Located 3 Bed, 2 Bath w/ Private Heated Pool!, Key West Dreamin' - Private Pool Steps Off Duval, Perfect Location, Private Heated Pool, Pristine Luxury Home!, **THE CONTENTED CRANE @ OLD TOWN** Home & Pool Near Duval + LAST KEY SERVICES..., HAVANA DAYDREAMING ~ Waterfront 1 BR/1 Ba w/ Dockage & Hot Tub!, INCOMMUNICADO ~ Waterfront 2 BR/2 Ba w/ Dockage and Hot Tub!, Key West Caribbean Cottage - On Duval St w Private Pool, LADY ADMIRAL ~Sweet cottage & guest house with private heated pool off Duval!, Road's End | Prime Old Town Location! Updated Home w/ Pool, PAGITT HOUSE - 4/3.5 - OLD TOWN KEY WEST WITH POOL!, SEVENTH HEAVEN~Waterfront 5 BR, 4 Ba Townhome with Pool, Elevator & Dockage!, Amelia`s Hideaway - Hidden Key West Courtyard - Steps off Duval w Private Pool |
Top trending hotels in Key West

Margaritaville Beach House Key West
More Destinations
- Hotels near Duval Street
- Hotels near Ernest Hemingway Home and Museum
- Hotels near Fort Zachary Taylor Historic State Park
- Aparthotels in Key West
- Apartments in Key West
- B&B in Key West
- Condo Rentals in Key West
- Cottages in Key West
- Guest Houses in Key West
- Hostels in Key West
- Resorts in Key West
- All Inclusive Hotels in Key West
- Apartment Hotels in Key West
- Arcade Hotels in Key West
- Beach Hotels in Key West
- Cheap Hotels in Key West
- Golf Hotels in Key West
- Highgate Independent Hotels in Key West
- Hilton Hotels in Key West
- Hotels with a Lazy River in Key West
- Hotels with Balconies in Key West
- Hotels with Free Breakfast in Key West
- Hotels with a Gym in Key West
- Hotels with Free Parking in Key West
- Hotels with Parking in Key West
- Hotels with Pool in Key West
- Hotels with Room Service in Key West
- Independent Hotels in Key West
- Luxury Hotels in Key West
- Oceanfront Hotels in Key West
- Hotels with Shopping in Key West
- Spa Hotels in Key West
- Hotels with a Waterpark in Key West
- Wyndham Hotels in Key West
- Houseboats in Key West
- Motels in Key West
- Hotels near Mallory Square
- Old Town Key West Hotels
- White Street Gallery District Hotels
- Flights to Key West
- Flights from Auckland to Key West
- Flights from Charlotte to Key West
- Flights from Chicago to Key West
- Flights from Dallas to Key West
- Flights from New Orleans to Key West
- Flights from Stockholm to Key West
- Flights from Sydney to Key West
- Flights from Washington to Key West
- Flights from Perth to Key West
- Flights from St. George's Parish to Key West
- Flights from Mildura to Key West
- Flights from Huntley to Key West
- Flights from Roma to Key West
- Flights from Thangool to Key West
- Flights from Amarillo to Key West
- Flights from Windhoek to Key West
- Flights from Gibson to Key West
- Flights from Galiwinku to Key West
- Flights from Cundletown to Key West
- Flights from Cairns to Key West
- Flights from Peoria to Key West
- Flights from Mackay to Key West
- Flights from Managua to Key West
- Flights from Norfolk Island to Key West
- Flights from Olympic Dam to Key West
- Flights from Utqiagvik to Key West
- Flights from Coffs Harbour to Key West
- Flights from Dubbo to Key West
- Ace Rental Cars in Key West
- Addcar rental Rental Cars in Key West
- Advantage Rent-A-Car Rental Cars in Key West
- Apex Car Rentals Rental Cars in Key West
- Car hire near Harry S. Truman Little White House
- Car hire Key West
- Car hire near Oldest House Museum and Garden
- Convertible Car Hire in Key West
- Dirent Rental Cars in Key West
- Dollar Rent A Car Rental Cars in Key West
- Drive-A-Matic Rental Cars in Key West
- Firefly Rental Cars in Key West
- First-Car Rental Cars in Key West
- First Car Rental Rental Cars in Key West
- Get Your Car Rental Cars in Key West
- Goldcar rental Rental Cars in Key West
- Keddy By Europcar Rental Cars in Key West
- Mex Rent A Car Rental Cars in Key West
- Midway Car Rental Rental Cars in Key West
- Offer Car Hire Rental Cars in Key West Historic District
- Priceless Car Rental Rental Cars in Key West
- Redspot Rental Cars in Key West
- Rhodium Rental Cars in Key West
- Right-Cars Rental Cars in Key West
- Sicily By Car Rental Cars in Key West
- Surprice Car Rentals Rental Cars in Key West
- Thrifty EU Rental Cars in Key West
- U-Save Rental Cars in Key West
- United Rental Cars in Key West
- Zezgo Rental Cars in Key West
^Eligibility requirements and conditions apply









