Cow Key Vacation Rentals

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Our top choices for Cow Key vacation rentals

Houseboat in Stock Island

Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
$355 nightly
The price is $400
Jan 6 - Jan 7, 2026
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
3.5 star property
10.0 out of 10, Exceptional, (1)
"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
Jan 16 - Jan 17, 2026
Total with taxes and fees
Atlantic View Luxury Villa with Pool
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
$548 nightly
The price is $610
Jan 10 - Jan 11, 2026
Total with taxes and fees
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
$563 nightly
The price is $625
Jan 18 - Jan 19, 2026
Total with taxes and fees
SAVE BIG $$ JANUARY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice place "
United States
Pawel
$582 nightly
The price is $655
Jan 26 - Jan 27, 2026
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
10.0 out of 10, Exceptional, (4)
"Beautiful "
United States
Lisa P.
$920 nightly
The price is $1,021
Jan 3 - Jan 4, 2026
Total with taxes and fees
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
8.6 out of 10, Excellent, (164)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
United States
Andrea S.
$341 nightly
The price is $379
Jan 19 - Jan 20, 2026
Total with taxes and fees
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Vacation Home in Cudjoe Key

Post Card Point #319 - Ocean Views!
10.0 out of 10, Exceptional, (49)
"The Post Card Point was absolutely stunning. Very clean and welcoming. Perfect access to fishing, diving, lobstering! Filet Table right on the water. We loved it :) will definitely be back!!!"
United States
Dave J.
$857 nightly
The price is $951
Jan 2 - Jan 3, 2026
Total with taxes and fees
Post Card Point #319 - Ocean Views!
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
$451 nightly
The price is $501
Jan 4 - Jan 5, 2026
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
10.0 out of 10, Exceptional, (24)
"This property is beautiful and the location is great as well. We will be back!"
United States
Patricia K.
$573 nightly
The price is $630
Jan 3 - Jan 4, 2026
Total with taxes and fees
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony & Pool!
9.6 out of 10, Exceptional, (415)
"We loved it here! Not very far from Duval street. "
United States
Keghan J.
$337 nightly
The price is $374
Jan 3 - Jan 4, 2026
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!
9.8 out of 10, Exceptional, (143)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
$910 nightly
The price is $1,011
Jan 6 - Jan 7, 2026
Total with taxes and fees
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Vacation Home in Raccoon Key

Springtide House at Lunara Bay
9.8 out of 10, Exceptional, (43)
"It was great. House was amazing"
United States
Ernest H.
$1,365 nightly
The price is $1,521
Jan 4 - Jan 5, 2026
Total with taxes and fees
Springtide House at Lunara Bay

Vacation Home in Raccoon Key

Capmar House at Lunara Bay
9.8 out of 10, Exceptional, (29)
"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
$1,390 nightly
The price is $1,546
Jan 5 - Jan 6, 2026
Total with taxes and fees
Capmar House at Lunara Bay
2.0 star property
10.0 out of 10, Exceptional, (2)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
$512 nightly
The price is $576
Jan 4 - Jan 5, 2026
Total with taxes and fees
Island View 1BR Residence With Balcony
9.8 out of 10, Exceptional, (116)
"Great location, close to everything family had a great time."
United States
rafael m.
$708 nightly
The price is $786
Jan 4 - Jan 5, 2026
Total with taxes and fees
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
9.8 out of 10, Exceptional, (30)
"I stayed at this property for 3 nights and it was wonderful super clean and very comfortableJust minutes away from all the attractions and far away from the crowds. Really quiet at night A I really recommend this property "
United States
domingo d.
$637 nightly
The price is $702
Jan 2 - Jan 3, 2026
Total with taxes and fees
The Cat Island Suite | Beautifully Renovated w/ Pool!

Vacation Home in Raccoon Key

The Seagate Estate at Lunara Bay
10.0 out of 10, Exceptional, (18)
"The perfect House , everything was good "
United States
CARLOS G.
$1,374 nightly
The price is $1,530
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Seagate Estate at Lunara Bay
2.0 star property
9.2 out of 10, Wonderful, (115)
"First day was very pleasant really enjoyed staying at the condo AC was cold everything worked well had a wonderful time"
United States
Mike R.
$594 nightly
The price is $660
Jan 4 - Jan 5, 2026
Total with taxes and fees
Stay at SUNRISE SUITES 203!

Vacation Home in Upper Sugarloaf Key

Palm - Beach Houses Key West
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.
$1,824 nightly
The price is $2,005
Jan 4 - Jan 5, 2026
Total with taxes and fees
Palm - Beach Houses 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 $374 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 Parking, Heated Pool - Sweet Caroline: Visitors like this Cow Key vacation home rental. It is located in the city center and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.