Cow Key Vacation Rentals

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Vacation Rentals in Cow Key

Cottage in Cudjoe Key

9.2 out of 10, Wonderful, (160)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
$285 nightly
The price is $316
Dec 6 - Dec 7
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West

Cottage in Cudjoe Key

8.2 out of 10, Very Good, (48)
"Very quiet place close to restaurants of all source we would like to come back and stay in the 3/2 cabin on the water with our grown children"
United States
Nathalie F.
$286 nightly
The price is $317
Nov 30 - Dec 1
Total with taxes and fees
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage in Cudjoe Key

8.6 out of 10, Excellent, (151)
"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.
$228 nightly
The price is $253
Dec 15 - Dec 16
Total with taxes and fees
Cottage with Pool and Boat Dockage just minutes to Key West!

Vacation Home in Cudjoe Key

9.6 out of 10, Exceptional, (100)
"Great location. "
United States
Davian k.
$413 nightly
The price is $459
Dec 1 - Dec 2
Total with taxes and fees
DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Houseboat in Stock Island

2.0 star property
8.8 out of 10, Excellent, (168)
"Location , staff , and aqua lodge were perfect."
United States
William
$265 nightly
The price is $298
Nov 30 - Dec 1
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

Vacation Home in Cudjoe Key

9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
$504 nightly
The price is $560
Dec 3 - Dec 4
Total with taxes and fees
DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cottage in Cudjoe Key

9.8 out of 10, Exceptional, (26)
"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"
United States
Patrick M.
$566 nightly
The price is $628
Dec 13 - Dec 14
Total with taxes and fees
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

Condo in Key West

8.8 out of 10, Excellent, (203)
"Good stay, everything was comfortable and ready to check in along with the typical amenities you would see at traditional hotels. Only stayed one night but there was a strong odor in the apartment, may have been from previous guests’ cooking but wasn’t unpleasant. Would stay again. "
United States
Juan E.
$245 nightly
The price is $273
Dec 1 - Dec 2
Total with taxes and fees
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

Vacation Home in Cudjoe Key

2.5 star property
9.6 out of 10, Exceptional, (11)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
$558 nightly
The price is $619
Nov 30 - Dec 1
Total with taxes and fees
Island Time #110 Ocean Views - Cudjoe Key

Vacation Home in Cutthroat Harbor Estates

8.4 out of 10, Very Good, (118)
"Great experience "
United States
Peyton S.
$483 nightly
The price is $536
Dec 6 - Dec 7
Total with taxes and fees
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Houseboat in Stock Island

7.8 out of 10, Good, (26)
"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
$454 nightly
The price is $504
Nov 29 - Nov 30
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Apartment in Old Town Key West

3.5 star property
8.4 out of 10, Very Good, (317)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
$268 nightly
The price is $301
Dec 8 - Dec 9
Total with taxes and fees
Hyatt Vacation Club at Sunset Harbor, Key West

Houseboat in Stock Island

9.8 out of 10, Exceptional, (34)
"Everything was very nice. Staff was friendly and helpful ."
United States
Debra
$307 nightly
The price is $341
Dec 8 - Dec 9
Total with taxes and fees
Living the Dream Key West Style

Condo in Key West

8.8 out of 10, Excellent, (117)
"We had fun, the room was just what we needed."
United States
Todd M.
$245 nightly
The price is $272
Nov 30 - Dec 1
Total with taxes and fees
Newly Furnished Suite with Pool, Hot Tub, Tennis, Balcony, Parking - Dog OK

Vacation Home in Upper Sugarloaf Key

10.0 out of 10, Exceptional, (14)
"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."
United States
Harvey(Tabb) M.
$1,553 nightly
The price is $1,706
Dec 11 - Dec 12
Total with taxes and fees
Palm - Beach Houses Key West

Cottage in Old Town Key West

9.8 out of 10, Exceptional, (21)
"Great little place, perfect for southernmost area."
United States
Lee G.
$286 nightly
The price is $315
Nov 30 - Dec 1
Total with taxes and fees
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!

Vacation Home in Stock Island

9.8 out of 10, Exceptional, (31)
"Nice stay and budget friendly. Hard to find a place to house 5 guys but this an accomplished that easily. Conveniently located to the airport and the restaurants in the area were great. If your trip in Key West involves the marina, the marina is just behind the hogfish grill. "
United States
Mike Q.
$665 nightly
The price is $738
Dec 1 - Dec 2
Total with taxes and fees
Paradise found

Cabin in Old Town Key West

9.0 out of 10, Wonderful, (100)
"Nice place, accurate description. "
United States
Sean F.
$325 nightly
The price is $361
Nov 30 - Dec 1
Total with taxes and fees
Cozy Cottage with Private Hot Tub, Tranquil Garden & Parking - Dogs OK

Condo in Beachside

8.6 out of 10, Excellent, (137)
"Nice area, location, and wonderful apartment!"
United States
Harald P.
$518 nightly
The price is $574
Nov 30 - Dec 1
Total with taxes and fees
Comfortable Condo with Pool, Private Balcony, & Beach Access

Condo in Meadows

9.2 out of 10, Wonderful, (15)
"Great location"
United States
Angie j.
$389 nightly
The price is $432
Dec 4 - Dec 5
Total with taxes and fees
Downtown Key West 2BR/2BA•Pool, Dock, Pet "Aruba"
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 $272 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?

Private Heated Pool & Near Duval - The Curry House: Visitors like this Cow Key vacation home rental. It is located in the city center and has a balcony, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities like a microwave and a coffee maker can make your vacation run smoothly.

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 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.