Cow Key Vacation Rentals

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Our top choices for Cow Key vacation rentals

Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (157 reviews)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."
United States
Richard S.
$285 nightly
The price is $316
Jan 31 - Feb 1
Total with taxes and fees
Cottage with Pool and Boat Dockage just minutes to Key West!

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
9.0 out of 10, Wonderful, (54 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
$402 nightly
The price is $447
Feb 2 - Feb 3
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (163 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
$311 nightly
The price is $345
Feb 15 - Feb 16
Total with taxes and fees
Cottage with swimming pool and dockage, just minutes to Key West!

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
$881 nightly
The price is $991
Jan 30 - Jan 31
Total with taxes and fees
Atlantic View Luxury Villa with Pool

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (176 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
$426 nightly
The price is $474
Feb 6 - Feb 7
Total with taxes and fees
Waterfront Home

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (165 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
$337 nightly
The price is $375
Feb 8 - Feb 9
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (102 reviews)
"Great location. "
United States
Davian k.
$492 nightly
The price is $548
Feb 4 - Feb 5
Total with taxes and fees
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (173 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
$337 nightly
The price is $379
Feb 4 - Feb 5
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
9.0 out of 10, Wonderful, (92 reviews)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
$434 nightly
The price is $482
Feb 1 - Feb 2
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"Nice place "
United States
Pawel
$968 nightly
The price is $1,090
Feb 2 - Feb 3
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.8 out of 10, Good, (26 reviews)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
$451 nightly
The price is $501
Feb 1 - Feb 2
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (19 reviews)
"The perfect House , everything was good "
United States
CARLOS G.
$1,541 nightly
The price is $1,710
Feb 3 - Feb 4
Total with taxes and fees
The Seagate Estate at Lunara Bay

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (52 reviews)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
$408 nightly
The price is $453
Feb 1 - Feb 2
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
$608 nightly
The price is $676
Feb 16 - Feb 17
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
9.8 out of 10, Exceptional, (40 reviews)
"Perfect, just perfect!"
United States
Mikael
$480 nightly
The price is $533
Feb 2 - Feb 3
Total with taxes and fees
Living the Dream Key West Style

Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (41 reviews)
"Beautiful House, super clean, perfect location "
United States
carlos s.
$1,695 nightly
The price is $1,881
Jan 31 - Feb 1
Total with taxes and fees
Suncoast House at Lunara Bay

Mastway House at Lunara Bay - Wellness Home

Mastway House at Lunara Bay - Wellness Home
Raccoon Key
9.6 out of 10, Exceptional, (32 reviews)
"The house was very clean and the neighborhood was in a perfect area and the neighbors were very friendly. Perfect get away!"
United States
Rachael S.
$1,796 nightly
The price is $1,994
Feb 9 - Feb 10
Total with taxes and fees
Mastway House at Lunara Bay - Wellness Home

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (150 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
$649 nightly
The price is $721
Feb 6 - Feb 7
Total with taxes and fees
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (158 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
$627 nightly
The price is $696
Feb 15 - Feb 16
Total with taxes and fees
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"House was spotless. Pool lights blinked on and off all night but not a problem. "
United States
Emmett A.
$1,541 nightly
The price is $1,710
Feb 1 - Feb 2
Total with taxes and fees
Capmar House at Lunara Bay
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

Find out more about Cow Key

Everything you need to know about Cow Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cow Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cow Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cow Key vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cow Key. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cow Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $315 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cow Key rentals

At Expedia, we put the best Cow Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cow Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cow Key vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cow Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Cow Key?

Yes, we have vacation rentals near well known local attractions in Cow Key, or you can select a more secluded option if you're looking for relaxation. Cow Key is known for its restaurants and shopping. Make sure you have time to check out the beaches while you're in the area.

What are some of the best vacation rentals that Cow Key has to offer?

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West: Visitors like this Cow Key vacation home rental. It offers an outdoor pool, a patio, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Make the most of the garden in this rental home to help you unwind.

What can I see and do in Cow Key?

Explore the area and family-friendly sights such as Key West Shipwreck Museum, or get out into nature at a spot like Key West Tropical Forest and Botanical Garden. In the larger area, you’ll find Duval Street and Stock Island Yacht Club & Marina.

What are vacation rentals like in Cow Key?

Vacation rentals are private accommodations you can stay in for several days or more in Cow Key. Vacation rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips.