Cow Key Vacation Rentals

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Our top choices for Cow Key vacation rentals

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, (56 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
$410 nightly
The price is $455
Feb 23 - Feb 24
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (178 reviews)
"The property needed a deep clean, dirty AC grills, etc. space needs to be updated. It served us well as a "motel" space, but lacked the upkeep and quality for a vacation space."
United States
Lyndon B.
$407 nightly
The price is $452
Feb 23 - Feb 24
Total with taxes and fees
Waterfront Home

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
$493 nightly
The price is $554
Mar 2 - Mar 3
Total with taxes and fees
Resort View 1BR Suite With Direct Pool Access

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (163 reviews)
"Very convenient to Restaurants & nice drive to Key West"
United States
Kim V.
$398 nightly
The price is $441
Mar 14 - Mar 15
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West

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, (151 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.
$657 nightly
The price is $729
Feb 23 - Feb 24
Total with taxes and fees
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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.
$318 nightly
The price is $352
Mar 12 - Mar 13
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
9.0 out of 10, Wonderful, (93 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.
$480 nightly
The price is $533
Mar 9 - Mar 10
Total with taxes and fees
Canal front, dockage, 2 bedroom, 2 bath

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
8.2 out of 10, Very Good, (56 reviews)
"It was like staying at my Grandmom's house--it was clean but bathroom and kitchen cabinet needed some attention. Still, we were very happy with bungalow 12 and would stay there again.We only stayed overnight but the little pool, beach and fire pit would be quite enjoyable had we stayed longer. Great price and very close to Key West. "
United States
joanne
$415 nightly
The price is $460
Mar 9 - Mar 10
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (84 reviews)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
$501 nightly
The price is $557
Mar 5 - Mar 6
Total with taxes and fees
SAVE BIG $$FEBRUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cutthroat Harbor Estates
8.4 out of 10, Very Good, (123 reviews)
"Great experience "
United States
Peyton S.
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

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.
$415 nightly
The price is $460
Feb 23 - Feb 24
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 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)
"The property had all the comforts of home. Plus, being able to enjoy the heated pool even through the overcast and windy conditions! The tropical landscaping and the dock on the bay was awesome!Would definitely recommend!!!"
United States
Anonymous traveler
$1,495 nightly
The price is $1,664
Mar 1 - Mar 2
Total with taxes and fees
Capmar House at Lunara Bay

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, (166 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
$292 nightly
The price is $324
Mar 10 - Mar 11
Total with taxes and fees
Cottage with swimming pool and 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
8.8 out of 10, Excellent, (90 reviews)
"Nice place to vacation "
United States
Kevin D.
$415 nightly
The price is $460
Mar 10 - Mar 11
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Quaint cottage, pool, dockage just minutes to Key West!

Quaint cottage, pool, dockage just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (150 reviews)
"great location, we are return visitors & will be back!"
United States
Shannon W.
$396 nightly
The price is $439
Feb 28 - Mar 1
Total with taxes and fees
Quaint cottage, pool, dockage just minutes to Key West!

Charming cottages, dockage, pool, just minutes to Key West

Charming cottages, dockage, pool, just minutes to Key West
Cudjoe Key
8.6 out of 10, Excellent, (122 reviews)
"host answered our question. Did not know w& d was coin washer and dryer"
United States
Robin D.
$372 nightly
The price is $413
Feb 24 - Feb 25
Total with taxes and fees
Charming cottages, dockage, pool, 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
$975 nightly
The price is $1,097
Feb 23 - Feb 24
Total with taxes and fees
Atlantic View Luxury Villa with Pool

Comfortable Condo with Pool, Private Balcony, & Beach Access

Comfortable Condo with Pool, Private Balcony, & Beach Access
Beachside
8.6 out of 10, Excellent, (140 reviews)
"Beautiful property! Pool was phenomenal. There is a men’s and a Womens sauna separately. The common area greenery is beautiful. Thank you"
United States
Amanda G.
$927 nightly
The price is $1,028
Mar 11 - Mar 12
Total with taxes and fees
Comfortable Condo with Pool, Private Balcony, & Beach Access

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.
$617 nightly
The price is $685
Feb 24 - Feb 25
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key

Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful! Pool was amazing!"
United States
Jennifer B.
$1,047 nightly
The price is $1,159
Feb 25 - Feb 26
Total with taxes and fees
Private and Exclusive Florida Keys Getaway
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 $309 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.