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
8.6 out of 10, Excellent, (53 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
Mar 21 - Mar 22
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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, (164 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, (153 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
Mar 14 - Mar 15
Total with taxes and fees
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (178 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
$411 nightly
The price is $456
Mar 20 - Mar 21
Total with taxes and fees
Waterfront Home

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

SAVE BIG $$$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (85 reviews)
"The rental was super clean and beautiful."
United States
christopher v.
$659 nightly
The price is $732
Apr 3 - Apr 4
Total with taxes and fees
SAVE BIG $$$ MARCH! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

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
$839 nightly
The price is $944
Mar 24 - Mar 25
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront

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.
$616 nightly
The price is $684
Mar 17 - Mar 18
Total with taxes and fees
Spanish Queen @Venture Out, Cudjoe Key

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.6 out of 10, Excellent, (95 reviews)
"We had a great time and will be back. "
United States
Michelle K.
$697 nightly
The price is $773
Mar 14 - Mar 15
Total with taxes and fees
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

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

SAVE BIG $$$ MARCH! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (104 reviews)
"Janet was great; quick to respond and very kind. Also the kayaks were fun and the beds were super comfy. "
United States
Lauren D.
$557 nightly
The price is $619
Mar 30 - Mar 31
Total with taxes and fees
SAVE BIG $$$ MARCH! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

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.
$1,699 nightly
The price is $1,880
Mar 24 - Mar 25
Total with taxes and fees
Private and Exclusive Florida Keys Getaway

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, (92 reviews)
"Nice place to vacation "
United States
Kevin D.
$415 nightly
The price is $460
Mar 16 - Mar 17
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Evershore Estate at Lunara Bay | Wellness Home

Evershore Estate at Lunara Bay | Wellness Home
Raccoon Key
9.8 out of 10, Exceptional, (27 reviews)
"The house is perfect for our family. Access to water, pool and close enough to key west!"
United States
John F.
$2,015 nightly
The price is $2,240
Mar 29 - Mar 30
Total with taxes and fees
Evershore Estate at Lunara Bay | Wellness Home

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
$1,541 nightly
The price is $1,710
Apr 13 - Apr 14
Total with taxes and fees
Capmar House at Lunara Bay

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (145 reviews)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
$920 nightly
The price is $1,021
Apr 11 - Apr 12
Total with taxes and fees
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

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, (163 reviews)
"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "
United States
Phillip
$589 nightly
The price is $653
Mar 25 - Mar 26
Total with taxes and fees
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
$574 nightly
The price is $646
Apr 13 - Apr 14
Total with taxes and fees
Resort View 1BR Suite With Direct Pool Access

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, (78 reviews)
"It was a nice location. 30” from Key West. "
United States
Linda N.
$415 nightly
The price is $460
Mar 14 - Mar 15
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

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, (29 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
$512 nightly
The price is $568
Apr 12 - Apr 13
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

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)
"Enjoyed the area. Not to far from Key West but far enough there wasn't a crowd"
United States
Donna P.
$398 nightly
The price is $441
Mar 19 - Mar 20
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, (124 reviews)
"Value for money: Fair This is a unit in a 3-unit divided house, not a cottage as described. It was clean, comfortable, quiet, and a good size, located a convenient drive to Key West. We enjoyed our stay."
United States
Laura
$372 nightly
The price is $413
Mar 20 - Mar 21
Total with taxes and fees
Charming cottages, dockage, pool, just minutes to 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

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 $313 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?

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West: You might want to consider this vacation home rental near Cow Key, which is located by the ocean and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family.

What can I see and do in Cow Key?

Explore the area and family-friendly sights such as Mel Fisher Maritime 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.