A waterfront with a pier, calm water, and houses with palm trees in the background.

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Sugarloaf Key houseboats

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

1. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (201 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is ￥16,937
￥45,921 total
includes taxes & fees
Oct 27 - Oct 28
Aqua Lodges at Hurricane Hole Marina
A balcony with a white wicker chair, a blue mat, and a red bench.

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

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Stock Island
8.0 out of 10, Very good, (14 reviews)
"This was the best place I have ever stayed! Tina is an amazing host, the energy was magnificent! "
United States
Ashley S.
The price is ￥26,825
￥48,591 total
includes taxes & fees
Oct 26 - Oct 27
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
A marina with numerous boats docked, a clear blue sky, and a distant view of the coastline.

3. Key West Sailboat Getaway

Key West Sailboat Getaway
Stock Island
9.4 out of 10, Exceptional, (3 reviews)
"This entire boat experience was totally awesome. I had never done anything like this before. Daniel The Host was great. I was able to be in contact with Daniel the whole entire time I was there, which was a week. He did a great job of answering all of my questions. Definitely something I would do again, especially with Daniel's boat."
United States
Thomas
The price is ￥46,904
￥68,965 total
includes taxes & fees
Nov 1 - Nov 2
Key West Sailboat Getaway
A marina with multiple sailboats docked, clear skies, and calm water.

4. Cozy Houseboat

Cozy Houseboat
Stock Island
10.0 out of 10, Exceptional, (1 review)
The price is ￥28,237
￥75,063 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Houseboat
A marina with boats docked, a swimming pool, and a building with a flat roof.

5. Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West

Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
Stock Island
10.0 out of 10, Exceptional, (6 reviews)
"Everything was great!"
United States
Terri F.
The price is ￥31,766
￥65,386 total
includes taxes & fees
Oct 26 - Oct 27
Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
A bedroom with a bed, a small table, a chair, a window, and a view of the water.

6. Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!

Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
Stock Island
6.8 out of 10, (13 reviews)
"My wife and I have been to Key West many times, and Liam's house boat has to be the coolest place we've stayed yet! "
United States
Mike W.
The price is ￥23,860
￥40,060 total
includes taxes & fees
Oct 27 - Oct 28
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
A white yacht named 'MÉDUSE' docked at a marina with other boats, palm trees, and a clear sky.

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

43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
Stock Island
10.0 out of 10, Exceptional, (7 reviews)
"We loved staying on this beautiful boat and all the amenities of the Perry Marina. Will definitely stay again: highly recommend "
United States
Erin S.
The price is ￥44,080
￥70,513 total
includes taxes & fees
Nov 11 - Nov 12
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
A marina with numerous boats, a modern building with a flat roof, and a parking area with a few cars.

8. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.6 out of 10, Good, (42 reviews)
"Great set up!!!"
United States
Benjamin
The price is ￥39,218
￥79,063 total
includes taxes & fees
Oct 26 - Oct 27
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
A boat deck with a Yamaha outboard motor, a white railing, and a view of the water and distant shoreline.

9. Docked in Paradise

Docked in Paradise
Stock Island
9.0 out of 10, Wonderful, (8 reviews)
"The houseboat is located in a great marina with a nice place to eat, have a drink, and enjoy a swim. The houseboat is very comfortable and clean. The host has excellent communication. It is only 3 miles away from Duval St but far enough away to be serene."
United States
Michael
The price is ￥54,905
￥100,143 total
includes taxes & fees
Oct 29 - Oct 30
Docked in Paradise
A hotel with a swimming pool, lounge chairs, and palm trees.

10. Counting Stars Sailboat Stay | 2 Cabins, Pool Access & Free Downtown Shuttle

Counting Stars Sailboat Stay | 2 Cabins, Pool Access & Free Downtown Shuttle
Stock Island
The price is ￥28,237
￥60,944 total
includes taxes & fees
Oct 26 - Oct 27
Counting Stars Sailboat Stay | 2 Cabins, Pool Access & Free Downtown Shuttle
A marina with boats, a lifeguard tower, and a sign for 'The Little Dipper Ice Cream Shop' during sunset.

11. Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West

Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
Stock Island
9.4 out of 10, Exceptional, (3 reviews)
"We had an amazing time. Would definitely stay there again!"
United States
Andrea S.
The price is ￥45,492
￥86,906 total
includes taxes & fees
Oct 26 - Oct 27
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
A hot tub with a view of a marina and boats during sunset.

12. Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (62 reviews)
"Great would definitely stay again "
United States
Zach C.
The price is ￥65,885
￥83,062 total
includes taxes & fees
Oct 26 - Oct 27
Living the Dream Key West Style
A two-story building with a sign reading 'SHIP STORE' at the entrance, a golf cart parked in front, and a clear blue sky.

13. 3-bedroom catamaran with pool and beach access in amazing Key West!

3-bedroom catamaran with pool and beach access in amazing Key West!
Stock Island
The price is ￥52,661
￥105,835 total
includes taxes & fees
Oct 26 - Oct 27
3-bedroom catamaran with pool and beach access in amazing Key West!
A modern building with a wooden deck overlooking a body of water, with palm trees and boats in the background.

14. Waterfront & Heated Pool - Away Awai Floating Villa

Waterfront & Heated Pool - Away Awai Floating Villa
Stock Island
9.4 out of 10, Exceptional, (8 reviews)
"A unique location with all you need"
United States
Stefanie S.
The price is ￥53,650
￥111,830 total
includes taxes & fees
Nov 18 - Nov 19
Waterfront & Heated Pool - Away Awai Floating Villa
A modern living room with a large window overlooking a marina with boats.

15. Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
The price is ￥51,610
￥109,536 total
includes taxes & fees
Oct 29 - Oct 30
Waterfront & Heated Pool - Break Awai Floating Villa
A pool area with palm trees, lounge chairs, and umbrellas.

16. 40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6

40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
Stock Island
10.0 out of 10, Exceptional, (1 review)
The price is ￥82,984
￥159,714 total
includes taxes & fees
Oct 26 - Oct 27
40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
A boat interior with a dining area, cushioned seating, and large windows offering views of the water and docked boats.

17. Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West

Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West
Stock Island
10.0 out of 10, Exceptional, (1 review)
"Check in process was very easy and host communication was very responsive."
United States
Aleksei B.
The price is ￥141,026
￥248,345 total
includes taxes & fees
Oct 26 - Oct 27
Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West
A modern kitchen with a large island, a seating area with a sofa and chairs, and a view of the marina through large windows.

18. Oceanfront - Break Awai x Away Awai Floating Villas

Oceanfront - Break Awai x Away Awai Floating Villas
Stock Island
The price is ￥90,671
￥190,166 total
includes taxes & fees
Nov 18 - Nov 19
Oceanfront - Break Awai x Away Awai Floating Villas
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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Top Sugarloaf Key Hotel Reviews

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

10/10 Excellent
"Wonderful stay. Staff was friendly and helpful, the breakfast is excellent and the location is perfect."
James 2-night trip
Posted 3 hours ago
Winslow's Bungalows - Key West Historic Inns

Find out more about Sugarloaf Key

Sugarloaf Key Houseboats information

Number of reviews
290
Accommodation
49 Houseboats
Lowest Price
￥45,921
Highest Price
￥248,345

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.
How can I find cheap houseboats in Sugarloaf Key?
If you're looking for good deals on houseboats in Sugarloaf Key, you'll want to add several filters to your search. Start by sorting your results by price so that the cheapest choices appear first on the page. Then, change your filters to suit your budget. Also, don't forget to sign up to our free rewards program, One Key™, for member-only offers. Expedia will help you find your perfect floating getaway whatever your budget or plans.
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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