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Featured Houseboats in Key West

Greet the Sunrise From Your Boat!
Greet the Sunrise From Your Boat!
Key West, FL
$250
This houseboat is a smoke-free houseboat.
Key West Sailing Adventure With Sunset Charter Included
Key West Sailing Adventure With Sunset Charter Included
3.0 out of 5.0 201 Williams Street; Historic Seaport, E-Dock Slips E-10, E-11, E-12, Key West, FL
$375
At Key West Sailing Adventure With Sunset Charter Included, guests have access to features like laundry facilities. Self parking is available for USD 30.00 per ...
KEY West Livin' Beautiful 50' Yacht With 3 Bed, 2 Bath Sleeps 6
KEY West Livin' Beautiful 50' Yacht With 3 Bed, 2 Bath Sleeps 6
Key West, FL
A fitness center and a sauna are features at this houseboat.
Eco Lodging at 5-star Resort - Perfect for Couples and Families
Eco Lodging at 5-star Resort - Perfect for Couples and Families
Key West, FL
Guests staying at this houseboat enjoy features like a fitness center. Helpful staff is there to provide concierge services, as well as offer insight about the ...
Key West: 3 BR, 2 BA Luxury Yacht; Special Now!
Key West: 3 BR, 2 BA Luxury Yacht; Special Now!
Key West, FL
$299
At this houseboat, guests enjoy features like beach towels.
Authentic Key West Experience ! Enjoy Life Aboard! Book a Key West Escape Now!
Authentic Key West Experience ! Enjoy Life Aboard! Book a Key West Escape Now!
Key West, FL
This houseboat is a smoke-free houseboat.
The Most Custom Vacation you Will Ever Have Right at Your Fingers!
The Most Custom Vacation you Will Ever Have Right at Your Fingers!
Key West, FL
$1,475
Staff members can help with accommodation requests, and provide concierge services.
Yacht in Paradise: 5 Star Marina, Pool, Bar & Restaurant, & Free Shuttle
Yacht in Paradise: 5 Star Marina, Pool, Bar & Restaurant, & Free Shuttle
Key West, FL
Situated on the waterfront, this houseboat is 0.6 mi (0.9 km) from Robbie's and within 3 mi (5 km) of Key West Harbour and Key West Golf Club. Key West Naval ...
THE Free Spirit - 75' OF Waterfront Paradise
THE Free Spirit - 75' OF Waterfront Paradise
Key West, FL
Guests staying at this houseboat enjoy features like a fitness center. Helpful staff is there to provide concierge services, as well as offer insight about the ...
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Houseboats

Book a houseboat in Key West
Take command of your next vacation…by taking the helm of a houseboat! Why debate over whether to stay home or go to the coast? A Key West houseboat rental lets you do both. It’s especially ideal if you’re traveling with a bunch of people, whether it’s family or friends, because it blends all the comfort of a “staycation” at home with adventure on the high seas. When you book through Orbitz, you’ll have everything you need to captain your new vacation home.

Key West houseboat vacations for everyone
Gather everyone you know, because most houseboats can sleep over 10 people while maintaining a cozy, small-house feel—without feeling cramped. There are showers and kitchens on almost every house boat, and some vessels come with hot tubs, wet bars and multiple TVs. Take your houseboat out to a particular spot in the water, or kick off a proper Key West adventure and travel from port to port. Your on-board crew will be so impressed with this unique vacation, they’ll probably start calling you “Skipper.” 

They’ll be even more impressed with the luxury house boats that are available. Think stunning décor, gorgeous artwork and even fireplaces for cool evenings on the water. Some even have glass bottoms so you can look right into the water beneath you.

When you want to give your sea legs a break, come ashore and do some sightseeing in Key West. Snap up a meal at one of the local restaurants, or do a little grocery shopping so you can cook once you’re back on the water. And don’t forget to look into fishing permits—there’s nothing like cooking up fresh-caught fish to really complete your houseboat experience. 

Hotel Options in Key West

See all 585 Properties in Key West
*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.