Search Houseboats in Sugarloaf Key

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Houseboats in Sugarloaf Key

Aqua Lodges at Hurricane Hole Marina
Accommodations float on calm waters, offering serene views of the surrounding landscape.

Aqua Lodges at Hurricane Hole Marina

2.0 star property
8.8 out of 10, Excellent, (160)
"The stay was beautiful "
The price is AU$365
includes taxes & fees
12 Aug - 13 Aug
Aqua Lodges at Hurricane Hole Marina
Super-cozy boat in 5 Star Key West Marina.
Marina

Super-cozy boat in 5 Star Key West Marina.

10.0 out of 10, Exceptional, (1)
"We had the best experience in this charming boathouse - it was just the right size for our group of four. From the moment we stepped inside, we felt right at home in its cozy and comfortable atmosphere, it felt like a bit of home away from home, but with the added novelty of being right on the water. Lori's thoughtful touches throughout made the small space extra inviting and relaxing. She and her husband were amazing hosts and always responded quickly to answer any of our questions, I loved...
Super-cozy boat in 5 Star Key West Marina.
NEW VRBO Listing! Elegant 40' Yacht in 5-Star Resort
Relax by the resort pool, surrounded by palm trees and a picturesque marina view.

NEW VRBO Listing! Elegant 40' Yacht in 5-Star Resort

10.0 out of 10, Exceptional, (1)
"We had a wonderful stay aboard the yacht! Everything was spotless, well-maintained, and even more beautiful than in the photos. The marina resort offered a peaceful and luxurious setting, and waking up on the water was truly unforgettable. Highly recommend this unique experience!"
NEW VRBO Listing! Elegant 40' Yacht in 5-Star Resort
34’ Catamaran Sailboat
Step aboard and enjoy the view from this cozy cabin, featuring a comfortable bench, a fully equipped kitchenette, and a control panel for your convenience.

34’ Catamaran Sailboat

9.4 out of 10, Exceptional, (35)
"Great time enjoying the keys like a pirate. "
34’ Catamaran Sailboat
Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!
Relax by the resort pool surrounded by palm trees and a paved walkway.

Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!

10.0 out of 10, Exceptional, (5)
"Our stay was wonderful. Tom was extremely helpful with anything we needed and great person to work with.would definitely stay again. "
Luxurious 40' Sailing Yacht located in a beautiful resort! VRBO NEW OFFER!
Brand new VRBO exclusive offer! 50 foot motor yacht in Key West!
Step aboard and enter the interior through the glass door.

Brand new VRBO exclusive offer! 50 foot motor yacht in Key West!

10.0 out of 10, Exceptional, (1)
"Having done power cat trips in BVI and Exumas we thought it would be fun to stay on a boat during our visit to Key West. Having the hotel pool and amenities made it feel like a resort stay. The boat was clean and spacious. Only negative is you can’t flush the toilet paper and have to put"
Brand new VRBO exclusive offer! 50 foot motor yacht in Key West!
Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew
Relax on the spacious deck with a comfortable seating area and flat-screen TV.

Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew

The price is AU$11,879
includes taxes & fees
13 Aug - 14 Aug
Luxurious "Atlantia" 2020 6-bedrooms 64ft yacht with full time crew
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Experience the charm of Key West at The Perry Hotel, where a beautifully designed sign welcomes you to a tropical oasis with lush greenery and stunning views.

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

7.8 out of 10, Good, (22)
"Great weekend everyone loved it."
The price is AU$770
includes taxes & fees
8 Aug - 9 Aug
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Charming catamaran sailboat with AC, pool in stock island yacht club, Key West.
Relax on the beach, surrounded by a tranquil atmosphere and a thatched-roof structure.

Charming catamaran sailboat with AC, pool in stock island yacht club, Key West.

10.0 out of 10, Exceptional, (2)
"We loved the settings, and Captain Mike is a wonderful, helpful host!The interior of the boat is not spacious, and is full of useful items available for our use.A highly recommended unusual stay.The pood and communal showers are excellent."
Charming catamaran sailboat with AC, pool in stock island yacht club, Key West.
TRAVEL THE KEYS OR JUST RELAX AT THE DOCK
Relax on the beach with comfortable seating and umbrellas, surrounded by calm waters and a boat on the horizon.

TRAVEL THE KEYS OR JUST RELAX AT THE DOCK

9.4 out of 10, Exceptional, (28)
"The marina is the perfect location! There are 4 bedrooms so it is perfect for a group of friends (all individual beds except the master). The kitchen was well stocked to make all means and the grill on the top deck was great!"
TRAVEL THE KEYS OR JUST RELAX AT THE DOCK
KEY WEST LIVIN' Beautiful 66’ Yacht with 4 bedrooms and 4 bath sleeping 6.
Step into the charming Hogfish Bar Grill, a rustic restaurant nestled among tropical vegetation on Stock Island.

KEY WEST LIVIN' Beautiful 66’ Yacht with 4 bedrooms and 4 bath sleeping 6.

9.0 out of 10, Wonderful, (106)
"Our stay was great! Host was very accommodating! We took advantage of chartering the smaller boat the host has out to the sandbar for a fun day out in the water. Would definitely recommend!Boat amenities were as expecting. They are on the process of making upgrades to the boat. They just did new flooring before our stay. "
KEY WEST LIVIN' Beautiful 66’ Yacht with 4 bedrooms and 4 bath sleeping 6.
Ocean views! <br>I didn’t do it too
Enjoy meals and relaxation on the covered deck with seating and kitchen area.

Ocean views! <br>I didn’t do it too

10.0 out of 10, Exceptional, (21)
"Successful"
Ocean views! <br>I didn’t do it too
Southern Bell is a Beautiful Houseboat cozy and relaxing.
Enjoy a serene view of the calm waters and distant shoreline from the comfort of your boat.

Southern Bell is a Beautiful Houseboat cozy and relaxing.

10.0 out of 10, Exceptional, (6)
"The houseboat was great. Right next to Key West in stock island. The host and his crew were excellent, couldn’t ask for a better stay and better people!"
Southern Bell is a Beautiful Houseboat cozy and relaxing.
Amazing 4 Bdrm, 4 Bath Catamaran - Purpus
Relax by the pool overlooking the marina, surrounded by palm trees and lounge chairs.

Amazing 4 Bdrm, 4 Bath Catamaran - Purpus

10.0 out of 10, Exceptional, (2)
"Boat was immaculate, and very roomy for the 8 of us. Property manager very pleasant and responsive to communication. Location was perfect, area was quiet, the hotel amenities and marina amenities were wonderful. Pools at hotel were beautiful and well maintained. We loved our stay! The shuttle to downtown key west, an amazing bonus, saved us lots of uber fairs."
Amazing 4 Bdrm, 4 Bath Catamaran - Purpus
2 Bedrooms, 1 Bath-42' Hatteras in Key West
Relax by the pool surrounded by palm trees and lounge chairs.

2 Bedrooms, 1 Bath-42' Hatteras in Key West

2 Bedrooms, 1 Bath-42' Hatteras in Key West
SPECIAL OFFER! 50 Foot Luxury Sailing Catamaran in Five Star Resort, Key West!
Relax by the resort pool overlooking the marina, surrounded by lounge chairs and palm trees.

SPECIAL OFFER! 50 Foot Luxury Sailing Catamaran in Five Star Resort, Key West!

SPECIAL OFFER! 50 Foot Luxury Sailing Catamaran in Five Star Resort, Key West!
Happy’s Houseboat Key West
Experience the nautical charm of this cozy cabin, complete with a control station, cushioned bench, and stunning water views.

Happy’s Houseboat Key West

9.2 out of 10, Wonderful, (20)
"We enjoyed the time there"
Happy’s Houseboat Key West
Waterfront & Heated Pool - Awai's Floating Villa
Enjoy waterfront views and serene surroundings from the spacious deck area with large windows and outdoor furniture.

Waterfront & Heated Pool - Awai's Floating Villa

10.0 out of 10, Exceptional, (1)
"We enjoyed our stay. The boat was comfortable, clean and at a perfect location. Having coffee on the rooftop each morning, was a perfect way to start the day. Shuttle service to Downtown was perfect, no need for a rental car. "
The price is AU$1,270
includes taxes & fees
17 Aug - 18 Aug
Waterfront & Heated Pool - Awai's Floating Villa
Cozy Houseboat “Wild One”
Property grounds

Cozy Houseboat “Wild One”

9.8 out of 10, Exceptional, (10)
"We loved our stay! It was a perfect getaway/honeymoon spot for us. Ally and Tony communicated well and we loved their house boat. It was a fun, relaxing experience."
The price is AU$595
includes taxes & fees
15 Aug - 16 Aug
Cozy Houseboat “Wild One”
Ocean views! <br>No regrets
Relax on the deck with a clear view of the water and distant shoreline.

Ocean views! <br>No regrets

10.0 out of 10, Exceptional, (2)
"We had a fantastic five-day stay at "No Regrets." The location is about a 10 to 12-minute drive from Old Town. Despite being close to the airport, it remains very quiet. We also had the option to rent kayaks or paddleboards for the week. The surroundings are beautiful, with many mangroves nearby. The check-in process could use some improvement in terms of directions, but Bill was a great host and very responsive. Overall, it was an excellent stay!"
Ocean views! <br>No regrets
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

What is there to do in Sugarloaf Key near my houseboat?
If you're eager to discover the best of Sugarloaf Key, make your way to Florida Keys Beaches. It's a favourite with visitors and locals alike.