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A coastal property with a white and yellow house, surrounded by palm trees and a rocky shoreline.

Search Houseboats in Sugarloaf Key from CA $141

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    Check prices for these dates, December 14–15, 2026

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    Our top choices for Sugarloaf Key houseboats

    1. Aqua Lodges at Hurricane Hole Marina

    Three floating cabins with balconies, named Aqua-Lodge, docked on calm water with a clear sky and trees in the background.

    2. Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views

    A balcony with a white wicker chair, a blue mat, and a red bench.

    3. Key West Sailboat Getaway

    A marina with numerous boats docked, a clear blue sky, and a distant view of the coastline.

    4. 2-bedroom boat in fabulous Key West with kayaks

    A cozy interior with a patterned sofa, a small table, and a decorative curtain.

    5. Cozy Houseboat

    A marina with multiple sailboats docked, clear skies, and calm water.

    6. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

    A marina with numerous boats, a modern building with a flat roof, and a parking area with a few cars.

    7. 43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown

    A white yacht named 'MÉDUSE' docked at a marina with other boats, palm trees, and a clear sky.

    8. 3-bedroom catamaran with pool and beach access in amazing Key West!

    A two-story building with a sign reading 'SHIP STORE' at the entrance, a golf cart parked in front, and a clear blue sky.

    9. Counting Stars, sailboat. Resort and pool access

    A bed with a quilted grey bedspread and two pillows with a tropical print design.

    10. Sailboat Stay • Marina Pools • 15 Min Key West

    A modern cafe with wooden tables and chairs, artwork on the walls, and a large window providing natural light.

    11. Living the Dream Key West Style

    A hot tub with a view of a marina and boats during sunset.

    12. Docked in Paradise

    A boat deck with a Yamaha outboard motor, a white railing, and a view of the water and distant shoreline.

    13. Waterfront & Heated Pool - Away Awai Floating Villa

    A modern building with a wooden deck overlooking a body of water, with palm trees and boats in the background.

    14. Waterfront & Heated Pool - Break Awai Floating Villa

    A modern living room with a large window overlooking a marina with boats.

    15. 40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6

    A pool area with palm trees, lounge chairs, and umbrellas.

    16. Oceanfront - Break Awai x Away Awai Floating Villas

    A modern kitchen with a large island, a seating area with a sofa and chairs, and a view of the marina through large windows.

    17. Original Tiki Suite — Unique Floating Bungalow on the water in Key West, FL

    A room with a view of the sea, two glasses of white wine on a wooden table, and a woven chair.

    18. The Grand Tiki at Tiki Suites – A Floating Oasis in Key West

    A floating wooden structure with a thatched roof, a hammock, and a small seating area, situated on calm water.

    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.

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    Learn more about Sugarloaf Key

    Kayak through mangrove tunnels and spot colourful fish in the crystal-clear waters surrounding this laid-back island. Unwind on Sugarloaf Beach's white sands or explore Upper Sugarloaf Sound, where local boaters know the best snorkelling spots.

    See all hotels in Sugarloaf Key

    A coastal property with a white and yellow house, surrounded by palm trees and a rocky shoreline.

    Frequently Asked Questions

    Why book your houseboat in Sugarloaf Key with Expedia?

    Reserving a houseboat in Sugarloaf Key is as simple as entering your travel dates and choosing the option that suits your style. On the lookout for a floating retreat that's inexpensive or upscale, or a stay that also includes a hot tub? Use Expedia's search filters to narrow your results even further and find your ideal match.

    What is there to do in Sugarloaf Key near my houseboat?

    The best travel accessory is a well-planned itinerary. Florida Keys Beaches is a terrific place to begin your adventures in Sugarloaf Key.

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