Sugarloaf Key Houseboats

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

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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

Stock Island

Darren

HK$2,328 total

includes taxes & fees

10 Nov - 11 Nov

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

2. Aqua Lodges at Hurricane Hole Marina

Stock Island

Kagni

HK$2,501 total

includes taxes & fees

12 Nov - 13 Nov

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

3. Key West Sailboat Getaway

Stock Island

""Blown Away" is a wonderful option for travelers looking for a unique stay near Key West. David was a super helpful host. The boat was the perfect size for my friend and me to stay for the weekend. We really enjoyed the outside area on the boat and all the amenities in the marina. Definitely recommend Portside Bar and Grill for food close by. The shuttle from the front of the hotel was also great for exploring Duval."

Caroline W.

HK$2,266 total

includes taxes & fees

12 Nov - 13 Nov

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

4. Cozy Houseboat

Stock Island

HK$3,464 total

includes taxes & fees

9 Nov - 10 Nov

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

5. 3-bedroom catamaran with pool and beach access in amazing Key West!

Stock Island

HK$5,073 total

includes taxes & fees

11 Nov - 12 Nov

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

6. Living the Dream Key West Style

Stock Island

Zach C.

HK$4,009 total

includes taxes & fees

9 Nov - 10 Nov

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

7. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

Stock Island

Benjamin

HK$3,640 total

includes taxes & fees

8 Nov - 9 Nov

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

Stock Island

Terri F.

HK$3,090 total

includes taxes & fees

17 Nov - 18 Nov

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

9. 43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown

Stock Island

Erin S.

HK$3,369 total

includes taxes & fees

11 Nov - 12 Nov

A hotel with a swimming pool, lounge chairs, and palm trees.

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

Stock Island

HK$2,725 total

includes taxes & fees

9 Nov - 10 Nov

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

Stock Island

Andrea S.

HK$4,558 total

includes taxes & fees

16 Nov - 17 Nov

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

12. Docked in Paradise

Stock Island

Michael

HK$4,796 total

includes taxes & fees

12 Nov - 13 Nov

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

13. Waterfront & Heated Pool - Away Awai Floating Villa

Stock Island

Stefanie S.

HK$4,970 total

includes taxes & fees

30 Nov - 1 Dec

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

14. Waterfront & Heated Pool - Break Awai Floating Villa

Stock Island

HK$4,970 total

includes taxes & fees

30 Nov - 1 Dec

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

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

Stock Island

HK$7,367 total

includes taxes & fees

9 Nov - 10 Nov

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

16. Oceanfront - Break Awai x Away Awai Floating Villas

Stock Island

HK$8,996 total

includes taxes & fees

9 Nov - 10 Nov

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

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

Meadows

HK$6,604 total

includes taxes & fees

25 Nov - 26 Nov

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

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

Meadows

Shawn H.

HK$7,947 total

includes taxes & fees

12 Nov - 13 Nov

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Top Sugarloaf Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

10/10 Excellent

"Beautiful hotel, loved our stay"

Parrot Key Hotel & Villas

8/10 Good

"We had a fantastic stay at Parrot Key Resort in Key West. The property is beautiful and very well kept, the pools were nice, and our room was clean and spacious. I do wish they’d made better use of all that space. A little more storage, seating, and somewhere to set our stuff down would’ve made a difference. I would’ve liked the option to park my own car instead of paying over $30 a night for valet, and I didn’t feel like we got much out of the resort fee. The minibar prices were insane. A full liter of vodka costs less than the 375 mL bottle in the room. At that price, it feels like they’re taking advantage of people coming back after a night out. Overall, we really enjoyed our stay. I’d stay here again, reluctantly pay for valet, and happily spend another afternoon by the pool."

Hilton Key West Resort & Marina

8/10 Good

"The property is beautiful - we enjoyed the room, the pool. The bed was comfortable. We enjoyed the robes they offered to the guests. The room was quite spacious as well and our room had a balcony and overlooked the pool (building 3). We participated in some of the activities that the resort had (the yoga was the best!) There were just a few things that happened which is why I gave it 4 stars. We had arrived early and they said our room was being cleaned and they would call us. We waited 3 hours, They never called so we just went back and they forgot they said. When we got our room - the toilet didn't work. Things happen - no big deal. The next day tho - housekeeping never cleaned our room - I had to call twice. After that tho - they did clean our room daily. We hung out at the pool one day and someone came by with menus and said they would be back to take orders. They didn't come for over an hour - I had to actually call the restaurant and ask if they could have them come take our poolside order (as they offer this). If they are going to offer poolside - then they should have someone checking back with guests. Management did offer free breakfast for the issue with housekeeping and they did credit us the resort fee on the day of our arrival. The grounds were nice, the views were nice - I would go back, I'm just not sure if this would be my first option. I might check out another place first."

Find out more about Sugarloaf Key

Sugarloaf Key Houseboats information

Number of reviews	154
Accommodation	48 Houseboats
Lowest Price	HK$2,266
Highest Price	HK$8,996

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 programme, 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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Things to do in Ramrod Key

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sugarloaf Key houseboats

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

2. Aqua Lodges at Hurricane Hole Marina

3. Key West Sailboat Getaway

4. Cozy Houseboat

5. 3-bedroom catamaran with pool and beach access in amazing Key West!

6. Living the Dream Key West Style

7. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

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

9. 43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown

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

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

12. Docked in Paradise

13. Waterfront & Heated Pool - Away Awai Floating Villa

14. Waterfront & Heated Pool - Break Awai Floating Villa

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

16. Oceanfront - Break Awai x Away Awai Floating Villas

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

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

Find holiday rentals that suit your style

Top Sugarloaf Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Parrot Key Hotel & Villas

Hilton Key West Resort & Marina

DoubleTree Resort by Hilton Grand Key - Key West

Sugarloaf Key RV Resort & Cottages

The Reach Key West, Curio Collection by Hilton

Ibis Bay Beach Resort

Hilton Garden Inn Key West / The Keys Collection

Sugarloaf Key Hotel at KOA Resort

Find out more about Sugarloaf Key

Sugarloaf Key Houseboats information

Frequently asked questions

Explore a world of travel with Expedia

Search Houseboats in Sugarloaf Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Sugarloaf Key houseboats

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

2. Aqua Lodges at Hurricane Hole Marina

3. Key West Sailboat Getaway

4. Cozy Houseboat

5. 3-bedroom catamaran with pool and beach access in amazing Key West!

6. Living the Dream Key West Style

7. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

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

9. 43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown

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

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

12. Docked in Paradise

13. Waterfront & Heated Pool - Away Awai Floating Villa

14. Waterfront & Heated Pool - Break Awai Floating Villa

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

16. Oceanfront - Break Awai x Away Awai Floating Villas

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

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

Find holiday rentals that suit your style

Top Sugarloaf Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Find out more about Sugarloaf Key

Sugarloaf Key Houseboats information

Frequently asked questions

Explore a world of travel with Expedia