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

Cow Key Houseboat Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Cow Key houseboats

Exterior

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, (194 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
$249 nightly
The price is $280
Aug 23 - Aug 24
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
Marina

2. Key West Sailboat Getaway

Key West Sailboat Getaway
Stock Island
9.0 out of 10, Wonderful, (2 reviews)
"Definitely a unique property. I would recommend this stay for younger or more agile people. Knowing in advance that you will be stepping off the dock into the boat and going down steep steps to get into the living quarters can be tricky. Great Marina View with Marina amenities."
United States
Julia
$204 nightly
The price is $226
Aug 25 - Aug 26
Total with taxes and fees
Key West Sailboat Getaway
Exterior

3. 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, (39 reviews)
"Great stay and an excellent host! "
United States
Mike T.
$361 nightly
The price is $401
Aug 18 - Aug 19
Total with taxes and fees
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Property grounds

4. 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
$439 nightly
The price is $487
Aug 18 - Aug 19
Total with taxes and fees
Docked in Paradise
Terrace/patio

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

Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Stock Island
9.0 out of 10, Wonderful, (12 reviews)
"The host Tina is amazing! "
United States
Denise B.
$291 nightly
The price is $323
Aug 17 - Aug 18
Total with taxes and fees
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
Marina

6. Cozy Houseboat

Cozy Houseboat
Stock Island
10.0 out of 10, Exceptional, (1 review)
$428 nightly
The price is $476
Aug 16 - Aug 17
Total with taxes and fees
Cozy Houseboat
Marina

7. 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, (3 reviews)
"Everything was great!"
United States
Terri F.
$365 nightly
The price is $405
Aug 18 - Aug 19
Total with taxes and fees
Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
Marina

8. 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.
$428 nightly
The price is $475
Aug 18 - Aug 19
Total with taxes and fees
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
1 bedroom, desk, bed sheets

9. Affordable, Adventurous Houseboat on-the-water in Key West Florida

Affordable, Adventurous Houseboat on-the-water in Key West Florida
Stock Island
10.0 out of 10, Exceptional, (1 review)
"Wonderful getaway on the water! Quite the adventure! Comfy bed! Clean and well stocked! Would do it again!"
United States
lisa w.
$386 nightly
The price is $428
Aug 21 - Aug 22
Total with taxes and fees
Affordable, Adventurous Houseboat on-the-water in Key West Florida
2 bedrooms, iron/ironing board, WiFi, bed sheets

10. Waterfront & Heated Pool - Away Awai Floating Villa

Waterfront & Heated Pool - Away Awai Floating Villa
Stock Island
9.6 out of 10, Exceptional, (5 reviews)
"A unique location with all you need"
United States
Stefanie S.
$655 nightly
The price is $727
Aug 17 - Aug 18
Total with taxes and fees
Waterfront & Heated Pool - Away Awai Floating Villa
Pool

11. 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.
$479 nightly
The price is $532
Aug 18 - Aug 19
Total with taxes and fees
Living the Dream Key West Style
TV, offices

12. Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
$657 nightly
The price is $729
Aug 16 - Aug 17
Total with taxes and fees
Waterfront & Heated Pool - Break Awai Floating Villa
Outdoor pool

13. 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)
$920 nightly
The price is $1,021
Aug 15 - Aug 16
Total with taxes and fees
40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
Property grounds

14. Luxury 2 stateroom Yacht FREE TIME

Luxury 2 stateroom Yacht FREE TIME
Stock Island
10.0 out of 10, Exceptional, (2 reviews)
"My family and I had a wonderful stay on the boat. We had everything we could possibly need and then some. We would love to book the boat again next time we are down in Key West. Thank you for such a great experience. Cor (host) was great with our last minute booking and JD did a fantastic job setting everything up for us. A BIG Thank You from your Texas friends."
United States
Jennifer S.
$866 nightly
The price is $960
Aug 15 - Aug 16
Total with taxes and fees
Luxury 2 stateroom Yacht FREE TIME
Private kitchen

15. Stay Together, "Somewhere" - 4 Bed & 4 Bath - Catamaran in Key West

Stay Together, "Somewhere" - 4 Bed & 4 Bath - Catamaran in Key West
Stock Island
9.0 out of 10, Wonderful, (2 reviews)
"We thoroughly enjoyed our stay on "Somewhere" and the excursion was the highlight. The Yacht Club was also fantastic - great pool and we had a chance to meet fellow boaters and joined them for yoga. The boat was more spacious than we thought. "
United States
Michelle C.
$970 nightly
The price is $1,076
Aug 16 - Aug 17
Total with taxes and fees
Stay Together, "Somewhere" - 4 Bed & 4 Bath - Catamaran in Key West
Interior

16. Oceanfront - Break Awai x Away Awai Floating Villas

Oceanfront - Break Awai x Away Awai Floating Villas
Stock Island
$973 nightly
The price is $1,083
Aug 17 - Aug 18
Total with taxes and fees
Oceanfront - Break Awai x Away Awai Floating Villas
Dining

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
$1,420 nightly
The price is $1,576
Aug 15 - Aug 16
Total with taxes and fees
Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West
Terrace/patio

18. 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.
$1,085 nightly
The price is $1,204
Aug 23 - Aug 24
Total with taxes and fees
The Grand Tiki at Tiki Suites – A Floating Oasis in Key West
Interior

19. 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
$743 nightly
The price is $824
Aug 16 - Aug 17
Total with taxes and fees
Original Tiki Suite — Unique Floating Bungalow on the water in Key West, FL
Exterior

20. 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
$557 nightly
The price is $618
Aug 19 - Aug 20
Total with taxes and fees
3-bedroom catamaran with pool and beach access in amazing 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.
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Top Cow Key Hotel Reviews

Southwinds Motel

Southwinds Motel

10/10 Excellent
"Room was clean and the staff was very helpful. Location of motel was very convenient to get to Duval street "
Danielle 3-night trip
Posted less than an hour ago
Southwinds Motel

Find out more about Cow Key

Cow Key Houseboats information

Number of reviews
264
Accommodation
71 Houseboats
Lowest Price
$226
Highest Price
$1,576

Frequently asked questions

How much do houseboats in Cow Key cost?
Rates for houseboats in Cow Key range between $226 and $1,576 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 71 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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