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

Search Houseboats in Sugarloaf Key from CA $386

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Sugarloaf Key houseboats

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

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

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Stock Island
8.4 out of 10, Very good, (13 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 CA $255
CA $459 total
includes taxes & fees
Oct 3 - Oct 4
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
A marina with multiple sailboats docked, clear skies, and calm water.

2. Cozy Houseboat

Cozy Houseboat
Stock Island
10.0 out of 10, Exceptional, (1 review)
The price is CA $255
CA $683 total
includes taxes & fees
Oct 4 - Oct 5
Cozy Houseboat
A two-story building with a sign reading 'SHIP STORE' at the entrance, a golf cart parked in front, and a clear blue sky.

3. 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 CA $423
CA $896 total
includes taxes & fees
Oct 4 - Oct 5
3-bedroom catamaran with pool and beach access in amazing Key West!
Three floating cabins with balconies, named Aqua-Lodge, docked on calm water with a clear sky and trees in the background.

4. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (198 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is CA $128
CA $386 total
includes taxes & fees
Oct 5 - Oct 6
Aqua Lodges at Hurricane Hole Marina
A hot tub with a view of a marina and boats during sunset.

5. 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 CA $454
CA $576 total
includes taxes & fees
Oct 3 - Oct 4
Living the Dream Key West Style
A marina with numerous boats, a modern building with a flat roof, and a parking area with a few cars.

6. 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 CA $354
CA $719 total
includes taxes & fees
Oct 1 - Oct 2
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
A marina with numerous boats docked, a clear blue sky, and a distant view of the coastline.

7. 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 CA $424
CA $628 total
includes taxes & fees
Oct 15 - Oct 16
Key West Sailboat Getaway
A marina with boats docked, a swimming pool, and a building with a flat roof.

8. 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, (5 reviews)
"The marina was beautiful boat was quiet, relaxing close to everything but far enough away from the craziness of downtown. Plentyto do close by in and it’s a short drive to Key West my girlfriend said it was by far the best Mother’s Day ever couldn’t be happier. "
United States
Tyler L.
The price is CA $287
CA $594 total
includes taxes & fees
Oct 1 - Oct 2
Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
Open concept living area

9. Waterfront & Heated Pool - Away Awai Floating Villa

Waterfront & Heated Pool - Away Awai Floating Villa
Stock Island
9.8 out of 10, Exceptional, (6 reviews)
"A unique location with all you need"
United States
Stefanie S.
The price is CA $422
CA $940 total
includes taxes & fees
Oct 5 - Oct 6
Waterfront & Heated Pool - Away Awai Floating Villa
A boat deck with a Yamaha outboard motor, a white railing, and a view of the water and distant shoreline.

10. 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 CA $354
CA $719 total
includes taxes & fees
Oct 1 - Oct 2
Docked in Paradise
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
10.0 out of 10, Exceptional, (2 reviews)
"We had an amazing time. Would definitely stay there again!"
United States
Andrea S.
The price is CA $397
CA $774 total
includes taxes & fees
Oct 7 - Oct 8
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
A marina with multiple boats docked, a floating structure with a green deck and seating, and a building with large windows.

12. Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
The price is CA $420
CA $937 total
includes taxes & fees
Oct 1 - Oct 2
Waterfront & Heated Pool - Break Awai Floating Villa
A boat interior with a dining area, cushioned seating, and large windows offering views of the water and docked boats.

13. 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 CA $1,274
CA $2,244 total
includes taxes & fees
Oct 3 - Oct 4
Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West
A pool area with palm trees, lounge chairs, and umbrellas.

14. 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 CA $750
CA $1,453 total
includes taxes & fees
Oct 3 - Oct 4
40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
A modern kitchen with a large island, a seating area with a sofa and chairs, and a view of the marina through large windows.

15. Oceanfront - Break Awai x Away Awai Floating Villas

Oceanfront - Break Awai x Away Awai Floating Villas
Stock Island
The price is CA $780
CA $1,647 total
includes taxes & fees
Oct 27 - Oct 28
Oceanfront - Break Awai x Away Awai Floating Villas
A room with a view of the sea, two glasses of white wine on a wooden table, and a woven chair.

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

Original Tiki Suite — Unique Floating Bungalow on the water in Key West, FL
Meadows
The price is CA $780
CA $1,168 total
includes taxes & fees
Oct 4 - Oct 5
Original Tiki Suite — Unique Floating Bungalow on the water in Key West, FL
A floating wooden structure with a thatched roof, a hammock, and a small seating area, situated on calm water.

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

The Grand Tiki at Tiki Suites – A Floating Oasis in Key West
Meadows
10.0 out of 10, Exceptional, (1 review)
"The host and place where amazing!"
United States
Shawn H.
The price is CA $1,205
CA $1,706 total
includes taxes & fees
Oct 7 - Oct 8
The Grand Tiki at Tiki Suites – A Floating Oasis in Key West
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Sugarloaf Key Hotel Reviews

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"This property is nicer than anything we found closer to Duval Street. This property is 5 stars! Roomy, worth every penny. I loved my king size bed. I loved the properties gardens and the pools. It was quiet, private, and luxurious. I have one critique, valet parking is not needed. $30 for Valet is not needed."
Krystal 1-night trip
Posted 8 hours ago
Parrot Key Hotel & Villas

Find out more about Sugarloaf Key

Sugarloaf Key Houseboats information

Number of reviews
277
Accommodation
57 Houseboats
Lowest Price
CA $386
Highest Price
CA $2,244

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.

Explore a world of travel with Expedia