Cow Key Vacation Rentals

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Our top choices for Cow Key vacation rentals

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
The price is ¥101,144
¥174,823 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Atlantic View Luxury Villa with Pool
3.5 star property
8.6 out of 10, Excellent, (321)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is ¥37,631
¥47,568 total
includes taxes & fees
Dec 21 - Dec 22
Hyatt Vacation Club at Sunset Harbor, Key West
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
The price is ¥46,776
¥65,875 total
includes taxes & fees
Dec 18 - Dec 19
Island View 1BR Residence With Balcony

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
The price is ¥24,223
¥53,234 total
includes taxes & fees
Dec 21 - Dec 22
Aqua Lodges at Hurricane Hole Marina
3.0 star property
The price is ¥153,320
¥203,487 total
includes taxes & fees
Dec 29 - Dec 30
Coconut Mallory Marina and Resort Condo

Vacation Home in Old Town Key West

Contra House Key West
3.0 star property
Contra House Key West
2.0 star property
10.0 out of 10, Exceptional, (3)
"Nice place "
United States
Pawel
The price is ¥121,770
¥174,659 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Grand Marina Suite by Brightwild Waterfront
2.0 star property
10.0 out of 10, Exceptional, (1)
"Our family spent one night at Key West and we fully enjoyed our stay here. Room is very clean, stylish and spacious. Beds are comfortable."
United States
Xiulin
The Trinidad by Brightwild Pool View Parking

Apartment in Old Town Key West

Duval Dream Loft by Brightwild Right on Duval
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is ¥181,112
¥255,545 total
includes taxes & fees
Dec 24 - Dec 25
Duval Dream Loft by Brightwild Right on Duval

Vacation Home in Raccoon Key

Capmar House by Brightwild Huge Home Pool
2.0 star property
10.0 out of 10, Exceptional, (1)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is ¥163,988
¥288,607 total
includes taxes & fees
Dec 17 - Dec 18
Capmar House by Brightwild Huge Home Pool
2.0 star property
10.0 out of 10, Exceptional, (1)
The Grenada Suite Pool View Private Balcony

Apartment in Key West Historic District

The Bartlum Luxury Studio In Prime Location
2.0 star property
The price is ¥122,677
¥166,264 total
includes taxes & fees
Jan 2 - Jan 3, 2026
The Bartlum Luxury Studio In Prime Location

Apartment in Key West Historic District

Mesa House Uno by Brightwild Perfect Location
2.0 star property
The price is ¥110,176
¥152,344 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Mesa House Uno by Brightwild Perfect Location

Apartment in Old Town Key West

Sunnyside Up by Brightwild Pool Parking
3.0 star property
10.0 out of 10, Exceptional, (1)
The price is ¥147,357
¥208,152 total
includes taxes & fees
Dec 24 - Dec 25
Sunnyside Up by Brightwild Pool Parking

Apartment in Key West Historic District

New Coastal Rose - Bright Loft With High Ceilings
2.0 star property
New Coastal Rose - Bright Loft With High Ceilings

Apartment in Key West Historic District

New The Cottage at James House
2.0 star property
8.0 out of 10, Very Good, (2)
The price is ¥84,639
¥114,148 total
includes taxes & fees
Jan 11 - Jan 12, 2026
New The Cottage at James House
2.0 star property
The price is ¥154,685
¥226,082 total
includes taxes & fees
Dec 24 - Dec 25
Cloud Suite on Duval Luxury Condo Epic Location

Apartment in Old Town Key West

Sea Breeze by Brightwild Off-street Parking
2.0 star property
The price is ¥55,270
¥112,347 total
includes taxes & fees
Dec 17 - Dec 18
Sea Breeze by Brightwild Off-street Parking

Vacation Home in Old Town Key West

Contra House by Brightwild Luxury Home w Pool
2.0 star property
Contra House by Brightwild Luxury Home w Pool

Apartment in Old Town Key West

Poolside Suite by Brightwild Pvt Pool Parking
2.0 star property
The price is ¥78,398
¥130,572 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Poolside Suite by Brightwild Pvt Pool Parking
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

Search for holiday rentals in Cow Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Cow Key using one of the methods below:

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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?

Spacious home with pool & balcony - 1 block from Duval Street: Visitors like this Cow Key vacation home rental. It is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, 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 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.