Cow Key Vacation Rentals

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Our top choices for Cow Key vacation rentals

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
$975 nightly
The price is $1,097
Feb 22 - Feb 23
Total with taxes and fees
Atlantic View Luxury Villa with Pool

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
9.0 out of 10, Wonderful, (179 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
$355 nightly
The price is $400
Mar 1 - Mar 2
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
$940 nightly
The price is $1,057
Mar 2 - Mar 3
Total with taxes and fees
Resort View 2BR Residence

Ocean Front 2BR Residence

Ocean Front 2BR Residence
2.0 star property
Key West
$1,080 nightly
The price is $1,216
Mar 2 - Mar 3
Total with taxes and fees
Ocean Front 2BR Residence

Resort View 3BR Residence

Resort View 3BR Residence
2.0 star property
Key West
$1,191 nightly
The price is $1,340
Mar 2 - Mar 3
Total with taxes and fees
Resort View 3BR Residence

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
$507 nightly
The price is $570
Mar 2 - Mar 3
Total with taxes and fees
Resort View 1BR Suite With Direct Pool Access

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
$890 nightly
The price is $1,002
Feb 23 - Feb 24
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront

Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (2 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
$514 nightly
The price is $578
Mar 2 - Mar 3
Total with taxes and fees
Island View 1BR Residence With Balcony

Resort View 1BR Suite

Resort View 1BR Suite
2.0 star property
Key West
9.0 out of 10, Wonderful, (4 reviews)
"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "
United States
Michael
$520 nightly
The price is $585
Mar 2 - Mar 3
Total with taxes and fees
Resort View 1BR Suite

Sunnyside Up by Brightwild Pool Parking

Sunnyside Up by Brightwild Pool Parking
3.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
$1,513 nightly
The price is $1,702
Mar 17 - Mar 18
Total with taxes and fees
Sunnyside Up by Brightwild Pool Parking

Two Bedroom Residence With Balcony

Two Bedroom Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1 review)
"The roosters crowing early morning was irritating "
United States
Catherine
$870 nightly
The price is $978
Mar 2 - Mar 3
Total with taxes and fees
Two Bedroom Residence With Balcony

Ocean Front 1BR Suite With Direct Beach Access

Ocean Front 1BR Suite With Direct Beach Access
2.0 star property
Key West
10.0 out of 10, Exceptional, (2 reviews)
"Clean and spacious. Great view from room!"
United States
Jacqueline
$746 nightly
The price is $839
Mar 2 - Mar 3
Total with taxes and fees
Ocean Front 1BR Suite With Direct Beach Access

Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
$1,487 nightly
The price is $1,673
Feb 22 - Feb 23
Total with taxes and fees
Capmar House by Brightwild Huge Home Pool

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
Summerland Key
$829 nightly
The price is $933
Mar 12 - Mar 13
Total with taxes and fees
Starlight Serenity - Hideaway w Stunning Views

New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
2.0 star property
Raccoon Key
$2,620 nightly
The price is $2,947
Mar 1 - Mar 2
Total with taxes and fees
New Waterfront Home - Sunray House

Duval Dream Loft by Brightwild Right on Duval

Duval Dream Loft by Brightwild Right on Duval
2.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
$1,203 nightly
The price is $1,354
Mar 3 - Mar 4
Total with taxes and fees
Duval Dream Loft by Brightwild Right on Duval

The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1 review)
$659 nightly
The price is $741
Mar 1 - Mar 2
Total with taxes and fees
The Grenada Suite Pool View Private Balcony

Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
$643 nightly
The price is $723
Mar 2 - Mar 3
Total with taxes and fees
Ocean Front One Bedroom Residence

Brand New The Greenmoor House With Pool

Brand New The Greenmoor House With Pool
2.0 star property
Raccoon Key
$2,140 nightly
The price is $2,408
Feb 22 - Feb 23
Total with taxes and fees
Brand New The Greenmoor House With Pool

Waterfront Luxury Home - Tidelands House

Waterfront Luxury Home - Tidelands House
2.0 star property
Raccoon Key
$2,387 nightly
The price is $2,686
Feb 22 - Feb 23
Total with taxes and fees
Waterfront Luxury Home - Tidelands House
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 $311 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 Robbie's.

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.