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

Search Houseboats in Cow Key from CA $307

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

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, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is CA $134
CA $381 total
includes taxes & fees
Aug 26 - Aug 27
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
The price is CA $178
CA $307 total
includes taxes & fees
Sep 2 - Sep 3
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, (41 reviews)
"Great set up!!!"
United States
Benjamin
The price is CA $229
CA $547 total
includes taxes & fees
Sep 3 - Sep 4
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Marina

4. Cozy Houseboat

Cozy Houseboat
Stock Island
10.0 out of 10, Exceptional, (1 review)
The price is CA $249
CA $665 total
includes taxes & fees
Aug 26 - Aug 27
Cozy Houseboat
Property grounds

5. 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 $322
CA $665 total
includes taxes & fees
Sep 3 - Sep 4
Docked in Paradise
Marina

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, (4 reviews)
"Everything was great!"
United States
Terri F.
The price is CA $263
CA $552 total
includes taxes & fees
Sep 4 - Sep 5
Sailboat Stay • Marina Pools • Sleeps 4 • Stock Island, Key West
Terrace/patio

7. 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)
"The host Tina is amazing! "
United States
Denise B.
The price is CA $248
CA $443 total
includes taxes & fees
Aug 26 - Aug 27
Authentic 40' Hatteras Yacht Budget Keys Living & Ocean Views
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.
The price is CA $346
CA $699 total
includes taxes & fees
Aug 26 - Aug 27
Waterfront Yacht • Sleeps 4 • Deck Dining• Pools & Bar Access • 15 Min Key West
Interior

9. 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.
The price is CA $482
CA $1,003 total
includes taxes & fees
Sep 2 - Sep 3
Waterfront & Heated Pool - Away Awai Floating Villa
TV, offices

10. Waterfront & Heated Pool - Break Awai Floating Villa

Waterfront & Heated Pool - Break Awai Floating Villa
Stock Island
The price is CA $482
CA $1,003 total
includes taxes & fees
Sep 2 - Sep 3
Waterfront & Heated Pool - Break Awai Floating Villa
Outdoor pool

11. 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 $728
CA $1,411 total
includes taxes & fees
Sep 13 - Sep 14
40ft Sailboat, 3 Bdrm, 2 Bath, sleeps up to 6
Property grounds

12. 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.
The price is CA $690
CA $1,331 total
includes taxes & fees
Aug 26 - Aug 27
Luxury 2 stateroom Yacht FREE TIME
Private kitchen

13. 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.
The price is CA $687
CA $1,459 total
includes taxes & fees
Sep 9 - Sep 10
Stay Together, "Somewhere" - 4 Bed & 4 Bath - Catamaran in Key West
Interior

14. Oceanfront - Break Awai x Away Awai Floating Villas

Oceanfront - Break Awai x Away Awai Floating Villas
Stock Island
The price is CA $574
CA $1,398 total
includes taxes & fees
Aug 26 - Aug 27
Oceanfront - Break Awai x Away Awai Floating Villas
Dining

15. 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
The price is CA $1,237
CA $2,132 total
includes taxes & fees
Sep 4 - Sep 5
Luxurious 4-Bedroom Catamaran, sleeps up to 8 in delightful Key West
Interior

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 $757
CA $1,134 total
includes taxes & fees
Sep 3 - Sep 4
Original Tiki Suite — Unique Floating Bungalow on the water in Key West, FL
Terrace/patio

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 $1,170
CA $1,656 total
includes taxes & fees
Sep 2 - Sep 3
The Grand Tiki at Tiki Suites – A Floating Oasis in Key West
Exterior

18. 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 $395
CA $846 total
includes taxes & fees
Sep 2 - Sep 3
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

Havana Cabana at Key West

Havana Cabana at Key West

10/10 Excellent
"I enjoyed every minute of our stay. From when our plane arrived, we only had to wait about 20 minutes for the van to pick us up. The driver was very helpful and got us to the property and checked in quickly with no issues. We even got into our room over an hour early. Once we got situated we spoke with the concierge and set up a couple of activities for the week. We then took the free shuttle to Duval St. All of the drivers were a wealth of knowledge and helped us plan our stay. This was our first time to Key West but it definitely won’t be our last. I loved everything about the island and all the people seemed to be enjoying themselves. What little stress I brought with me was definitely gone within the first full day on island time. What a great time we had. All the staff was always friendly and welcoming and would go out of their way to assist you when they could. I will definitely stay at this location again. It’s perfectly set where you have access to anywhere on the island with the shuttle vans never far away. The porters definitely made me feel at home and they always had some stories of knowledge about the island. I wish I could give each of the porters an individual gift I would. They all deserve every bit of praise they get. Great job Havana Cabana. We will definitely be back !!!"
Chance 6-night trip
Posted 8 hours ago
Havana Cabana at Key West

Find out more about Cow Key

Cow Key Houseboats information

Number of reviews
73
Accommodation
71 Houseboats
Lowest Price
CA $307
Highest Price
CA $2,132

Frequently asked questions

How much do houseboats in Cow Key cost?
Rates for houseboats in Cow Key range between CA $307 and CA $2,132 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 9.1, 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 travellers 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.

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