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
    $245 nightly
    The price is $276 total per night from Oct 27 to Oct 28
    $276 total
    Oct 27 - Oct 28
    Total with taxes and fees
    8.8/10 Excellent! (97 reviews)
    Fisher Inn Resort & Marina

    Fisher Inn Resort & Marina

    84951 Overseas Hwy, Islamorada, FL
    $139 nightly
    The price is $156 total per night from Oct 21 to Oct 22
    $156 total
    Oct 21 - Oct 22
    Total with taxes and fees
    8/10 Very Good! (1,006 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 Oct 21 to Oct 22
    $168 total
    Oct 21 - Oct 22
    Total with taxes and fees
    7.6/10 Good! (825 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
24 Houseboats
Lowest Price
$156
Highest Price
$470
Popular accommodation
Treasure Harbor, Florida Keys Luxury Houseboat, Unique living on the Water WiFi, Mangrove Marina and Resort Aqualodge Houseboats, Aqua Lodge Houseboat "Yellow Tail ", Island Sanctuary Islamorada, Aqua Lodge Houseboat "Calypso", Amazing Yacht With Resort Amenities In The Heart Of Key Largo, Waterfront Sunset View Aqua Villa at Sea Biscuit @ Mangrove Resort LLC, 1.5 Bedroom, 1 bath with back deck. Pet friendly with 2 Queen and 2 twin beds.

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