A tropical island with clear blue waters, palm trees, and a thatched-roof hut.

Search Houseboats in Cudjoe Key from CA $408

  • 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
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Cudjoe Key houseboats

A row of floating houses with balconies, connected by walkways, on calm water.

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 CA $150
CA $408 total
includes taxes & fees
Oct 29 - Oct 30
Aqua Lodges at Hurricane Hole Marina
A covered outdoor area with a bamboo fence, a metal table with a woven chair, and a wind turbine in the background.

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, (15 reviews)
"6 of us stayed the weekend and it was great. The boat was clean and well stocked with many amenities. The hosts Glen and Abby were amazing. Anything we needed they were quick to oblige. They live on site so they are always there if needed. We are definitely returning next year."
United States
Darren
The price is CA $240
CA $437 total
includes taxes & fees
Oct 28 - Oct 29
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
A cozy interior with a patterned sofa, a small table, and a decorative curtain.

3. 2-bedroom boat in fabulous Key West with kayaks

2-bedroom boat in fabulous Key West with kayaks
Stock Island
The price is CA $252
CA $316 total
includes taxes & fees
Nov 1 - Nov 2
2-bedroom boat in fabulous Key West with kayaks
A modern kitchen with a black countertop, white cabinets, a stove, and a sink.

4. Cozy Houseboat

Cozy Houseboat
Stock Island
10.0 out of 10, Exceptional, (1 review)
The price is CA $252
CA $674 total
includes taxes & fees
Nov 1 - Nov 2
Cozy Houseboat
A swimming pool with lounge chairs and palm trees.

5. Key West Sailboat Getaway

Key West Sailboat Getaway
Stock Island
9.6 out of 10, Exceptional, (4 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 $279
CA $443 total
includes taxes & fees
Nov 11 - Nov 12
Key West Sailboat Getaway
A two-story building with a sign reading 'SHIP STORE' at the entrance, a golf cart parked in front, and a clear blue sky.

6. 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 $470
CA $952 total
includes taxes & fees
Oct 28 - Oct 29
3-bedroom catamaran with pool and beach access in amazing Key West!
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

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 $350
CA $711 total
includes taxes & fees
Nov 3 - Nov 4
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
A hot tub with a view of a marina and boats during sunset.

8. Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (63 reviews)
"Great would definitely stay again "
United States
Zach C.
The price is CA $588
CA $746 total
includes taxes & fees
Nov 13 - Nov 14
Living the Dream Key West Style
A bedroom with a bed, a small table, a chair, a window, and a view of the water.

9. 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 CA $213
CA $359 total
includes taxes & fees
Oct 29 - Oct 30
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
A marina with boats docked, a swimming pool, and a building with a flat roof.

10. 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 CA $284
CA $587 total
includes taxes & fees
Oct 28 - Oct 29
Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
A boat deck with a Yamaha outboard motor, a white railing, and a view of the water and distant shoreline.

11. 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 $490
CA $900 total
includes taxes & fees
Oct 29 - Oct 30
Docked in Paradise
A pool area with lounge chairs and palm trees.

12. 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 CA $394
CA $633 total
includes taxes & fees
Nov 11 - Nov 12
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
A hotel with a swimming pool, lounge chairs, and palm trees.

13. 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 CA $252
CA $547 total
includes taxes & fees
Oct 31 - Nov 1
Counting Stars Sailboat Stay | 2 Cabins, Pool Access & Free Downtown Shuttle
An aerial view of a resort with a central swimming pool surrounded by palm trees and sun loungers.

14. 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 CA $420
CA $799 total
includes taxes & fees
Oct 28 - Oct 29
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
A modern building with a wooden deck overlooking a body of water, with palm trees and boats in the background.

15. 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 CA $476
CA $1,004 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.

16. Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
The price is CA $441
CA $959 total
includes taxes & fees
Oct 29 - Oct 30
Waterfront & Heated Pool - Break Awai Floating Villa
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

17. 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 $741
CA $1,437 total
includes taxes & fees
Oct 28 - Oct 29
40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
A yacht docked at a marina with a 'WELCOME' mat featuring pineapple designs.

18. 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 $1,260
CA $2,219 total
includes taxes & fees
Oct 28 - Oct 29
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.

19. Oceanfront - Break Awai x Away Awai Floating Villas

Oceanfront - Break Awai x Away Awai Floating Villas
Stock Island
The price is CA $806
CA $1,721 total
includes taxes & fees
Nov 18 - Nov 19
Oceanfront - Break Awai x Away Awai Floating Villas
A thatched-roof bungalow on stilts over calm water, with a sunset in the background.

20. 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 $974
CA $1,492 total
includes taxes & fees
Nov 3 - Nov 4
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 Cudjoe Key Hotel Reviews

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"Great place to stay. Very clean and the staff were super helpful. The free shuttle was great."
Carolyn 2-night trip
Posted 2 hours ago
Blue Flamingo Resort Key West

Find out more about Cudjoe Key

Cudjoe Key Houseboats information

Number of reviews
356
Accommodation
61 Houseboats
Lowest Price
CA $408
Highest Price
CA $2,219

Frequently asked questions

Why book your houseboat in Cudjoe Key with Expedia?
Vacationing should be hassle-free, so if you're looking for houseboats at an affordable price, Expedia has your back. Keep costs down and choose a small and cozy option, or book a 5-star vessel and spoil your crew.

Explore a world of travel with Expedia