Compare Islamorada Houseboat Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Hotel Options in Islamorada

    Cheeca Lodge & Spa

    Cheeca Lodge & Spa

    81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
    The price is $319 per night from May 30 to May 31
    $319
    per night
    May 30 - May 31
    8.8/10 Excellent! (1,008 reviews)
    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    The price is $246 per night from May 30 to May 31
    $246
    per night
    May 30 - May 31
    8.8/10 Excellent! (1,339 reviews)
    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    The price is $288 per night from Jun 27 to Jun 28
    $288
    per night
    Jun 27 - Jun 28
    8.8/10 Excellent! (1,244 reviews)

Houseboats

Book a houseboat in Islamorada
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 Islamorada 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.

Islamorada 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 Islamorada 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 Islamorada. 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. 

Islamorada Houseboats essential information

Accommodation
Houseboats
Lowest Price
$246
Highest Price
$319
Popular accommodation
Cheeca Lodge & Spa, Chesapeake Beach Resort, Amara Cay Resort