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
    $237 nightly
    The price is $266 total per night from Aug 19 to Aug 20
    $266 total
    Aug 19 - Aug 20
    Total includes taxes and fees
    9/10 Wonderful! (47 reviews)
    Fisher Inn Resort & Marina

    Fisher Inn Resort & Marina

    84951 Overseas Hwy, Islamorada, FL
    $143 nightly
    The price is $161 total per night from Jul 23 to Jul 24
    $161 total
    Jul 23 - Jul 24
    Total includes taxes and fees
    7.8/10 Good! (1,003 reviews)
    Coconut Cove Resort and Marina

    Coconut Cove Resort and Marina

    84801 Overseas Highway, Islamorada, FL
    $149 nightly
    The price is $168 total per night from Jul 22 to Jul 23
    $168 total
    Jul 22 - Jul 23
    Total includes taxes and fees
    7.6/10 Good! (802 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
26 Houseboats
Lowest Price
$161
Highest Price
$424
Popular accommodation
Treasure Harbor, Lady Blue Yacht in FL KEYS, ARE YOU READY TO SPEND YOUR BEST HOLIDAYS AT SEA ???, Aqua Lodge Houseboat "Yellow Tail ", Charming house boat with 2 bedrooms and WiFi, AC in wonderful Islamorada, Amazing Yacht With Resort Amenities In The Heart Of Key Largo, Waterfront Sunset View Aqua Villa at Sea Biscuit @ Mangrove Resort LLC, Mangrove Marina and Resort Aqualodge Houseboats, Island Sanctuary Islamorada