A sunset over a beach with a wooden pier and a small structure on it.

Cow Key Houseboat Rentals

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  • Upfront pricing

    We are not like the others - we include taxes and fees

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 Cow 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
$261 nightly
The price is $293
Oct 28 - Oct 29
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
A swimming pool with lounge chairs and palm trees.

2. 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
$283 nightly
The price is $314
Nov 11 - Nov 12
Total with taxes and fees
Key West Sailboat Getaway
A modern kitchen with a black countertop, white cabinets, a stove, and a sink.

3. Cozy Houseboat

Cozy Houseboat
Stock Island
10.0 out of 10, Exceptional, (1 review)
$429 nightly
The price is $477
Nov 1 - Nov 2
Total with taxes and fees
Cozy Houseboat
A bedroom with a bed, a small table, a chair, a window, and a view of the water.

4. 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.
$228 nightly
The price is $253
Oct 29 - Oct 30
Total with taxes and fees
Florida Keys Living: Your Charming Houseboat Getaway in the Florida Keys!
A pool area with lounge chairs and palm trees.

5. 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.
$405 nightly
The price is $450
Nov 11 - Nov 12
Total with taxes and fees
43' Classic Trawler 5 Star Resort Pools, Views, Dining Free Shuttle to Downtown
A marina with boats docked, a swimming pool, and a building with a flat roof.

6. 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.
$378 nightly
The price is $420
Oct 28 - Oct 29
Total with taxes and fees
Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
A covered outdoor area with a bamboo fence, a metal table with a woven chair, and a wind turbine in the background.

7. 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
$277 nightly
The price is $308
Oct 28 - Oct 29
Total with taxes and fees
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
A boat deck with a Yamaha outboard motor, a white railing, and a view of the water and distant shoreline.

8. 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
$572 nightly
The price is $635
Oct 29 - Oct 30
Total with taxes and fees
Docked in Paradise
A cozy interior with a patterned sofa, a small table, and a decorative curtain.

9. 2-bedroom boat in fabulous Key West with kayaks

2-bedroom boat in fabulous Key West with kayaks
Stock Island
$206 nightly
The price is $229
Oct 28 - Oct 29
Total with taxes and fees
2-bedroom boat in fabulous Key West with kayaks
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
$348 nightly
The price is $387
Oct 28 - Oct 29
Total with taxes and fees
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.

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.
$496 nightly
The price is $551
Oct 28 - Oct 29
Total with taxes and fees
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.

12. 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.
$645 nightly
The price is $716
Nov 18 - Nov 19
Total with taxes and fees
Waterfront & Heated Pool - Away Awai Floating Villa
A hot tub with a view of a marina and boats during sunset.

13. 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.
$474 nightly
The price is $527
Oct 29 - Oct 30
Total with taxes and fees
Living the Dream Key West Style
A modern living room with a large window overlooking a marina with boats.

14. Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
$609 nightly
The price is $677
Oct 29 - Oct 30
Total with taxes and fees
Waterfront & Heated Pool - Break Awai Floating Villa
A two-story building with a sign reading 'SHIP STORE' at the entrance, a golf cart parked in front, and a clear blue sky.

15. 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
$605 nightly
The price is $672
Oct 29 - Oct 30
Total with taxes and fees
3-bedroom catamaran with pool and beach access in amazing Key West!
A pool area with lounge chairs and umbrellas, surrounded by palm trees.

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)
$912 nightly
The price is $1,013
Oct 28 - Oct 29
Total with taxes and fees
40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
A marina with numerous boats, a modern building with a flat roof, and a parking area with a few cars.

17. 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
$457 nightly
The price is $507
Nov 3 - Nov 4
Total with taxes and fees
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
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.
$1,427 nightly
The price is $1,583
Oct 28 - Oct 29
Total with taxes and fees
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
$1,086 nightly
The price is $1,208
Nov 18 - Nov 19
Total with taxes and fees
Oceanfront - Break Awai x Away Awai Floating Villas
A floating wooden structure with a thatched roof, a covered porch, and seating.

20. 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
$794 nightly
The price is $881
Nov 25 - Nov 26
Total with taxes and fees
Original Tiki Suite — Unique Floating Bungalow on the water in Key West, FL
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 Cow Key Hotel Reviews

Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

10/10 Excellent
"Cleanest resort in the keys!"
Gregory 3-night trip
Posted 1 hour ago
Hilton Key West Resort & Marina

Find out more about Cow Key

Cow Key Houseboats information

Number of reviews
355
Accommodation
64 Houseboats
Lowest Price
$293
Highest Price
$1,583

Frequently asked questions

How much do houseboats in Cow Key cost?
Rates for houseboats in Cow Key range between $293 and $1,583 per night. Whatever your budget, you're sure to find an awesome option for you and your crewmates. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best houseboats in Cow Key?
Take your pick of multiple houseboats in Cow Key for an unforgettable adventure on the water. These floating retreats have a total average guest review rating of 9.2, and one of the most sought-after is Key West Sailing Adventure With Sunset Charter Included. It has a 3-star rating and amenities including an art gallery and individually decorated rooms. Key West Yacht Life is also recommended by Expedia guests. This 4-star option offers a barbecue grill, a swimming pool and more.
How many houseboats are there in Cow Key?
You can choose from 64 houseboats in Cow Key. Whether you're vacationing with the family or arranging a weekend escape with your pals, Expedia will help you find the perfect getaway on the water.
Are there any family-friendly houseboats in Cow Key?
Check your crew in at Key West Sailing Adventure With Sunset Charter Included, a 3-star option sure to float everyone's boat. Conveniences here include a nearby beach and laundry facilities. Another family-friendly houseboat is Key West Yacht Life. WiFi and laundry facilities help make this 4-star property a hit with families planning a water-based vacation. Cow Key has tons of family-friendly attractions to check out that'll keep the kids entertained. Smathers Beach and South Beach promise fun for travelers of all ages.
Why book your houseboat in Cow Key with Expedia?
Booking a houseboat in Cow Key is as easy as entering your travel dates and selecting an option that meets your needs. Looking for a floating retreat that's luxurious or low cost, or a stay that also includes a hot tub and free WiFi? Use Expedia's search filters to narrow your results even further and find the ideal fit at the right price.
How can I find cheap houseboats in Cow Key?
If you're seeking terrific deals on houseboats in Cow Key, add a few filters to your search. Start by sorting your results by price so that the cheapest choices appear at the top of the list. Then, adjust your filters to match your budget. Expedia will help you find your dream floating escape whatever your plans or budget.

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