Compare Windley Key Houseboat Rentals

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Featured Houseboats in Windley Key

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Windley Key

    Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

    Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

    84001 Overseas Hwy Islamorada FL
    $336 nightly
    The price is $378 total per night from Jul 7 to Jul 8
    $378 total
    Jul 7 - Jul 8
    Total with taxes and fees
    9/10 Wonderful! (206 reviews)
    Fisher Inn Resort & Marina

    Fisher Inn Resort & Marina

    84951 Overseas Hwy Islamorada FL
    $188 nightly
    The price is $212 total per night from Jun 15 to Jun 16
    $212 total
    Jun 15 - Jun 16
    Total with taxes and fees
    8.2/10 Very Good! (1,012 reviews)
    Coconut Cove Resort and Marina

    Coconut Cove Resort and Marina

    84801 Overseas Highway Islamorada FL
    $179 nightly
    The price is $201 total per night from Jun 14 to Jun 15
    $201 total
    Jun 14 - Jun 15
    Total with taxes and fees
    9/10 Wonderful! (266 reviews)

Houseboats

Book a houseboat in Windley Key
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 Windley Key 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.

Windley Key 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 Windley Key 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 Windley Key. 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. 

Windley Key Houseboats essential information

Accommodation
19 Houseboats
Lowest Price
$201
Highest Price
$1,158
Popular accommodation
Treasure Harbor, Best Kept Secret! House Boat 70' Has Everything!, Aqua Lodge Houseboat "The Grey Lady", Aqua Lodge Houseboat "Tarpon", Aqua Lodge Houseboat "Captain's Quarters", Island Sanctuary Islamorada, Premium Floating Bungalow by Stay Ombi, Fla Keys Luxury Houseboat, Prime Location-Steps to Fun, Food & Water Adventures, Aqua Lodge Houseboat "Calypso"

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