A sunset over a beach with a wooden pier and a small structure on it.

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Our top choices for Cow Key holiday rentals

1. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is £241
includes taxes & fees
16 Nov - 17 Nov
Aqua Lodges at Hurricane Hole Marina

2. 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
The price is £519
includes taxes & fees
22 Nov - 23 Nov
Grand Marina Suite by Brightwild Waterfront

3. Lighthouse Suites Collection

Lighthouse Suites Collection
3.5 star property
Old Town Key West
10.0 out of 10, Exceptional, (2 reviews)
"My favorite place now. Won’t stay anywhere else. Lost track of the amount of my Key West stays, but this place has been the the most memorable."
United States
Melissa
The price is £643
includes taxes & fees
19 Nov - 20 Nov
Lighthouse Suites Collection

4. Contra House Key West

Contra House Key West
3.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Pool and outside was undesirable"
United States
Rosalie
The price is £905
includes taxes & fees
8 Dec - 9 Dec
Contra House Key West

5. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 reviews)
"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 £739
includes taxes & fees
16 Nov - 17 Nov
Atlantic View Luxury Villa with Pool

6. The Grenada Suite Pool View Private Balcony

The Grenada Suite Pool View Private Balcony
2.0 star property
Key West
9.0 out of 10, Wonderful, (2 reviews)
"A little dated, but clean and well located."
United States
Luis
The price is £422
includes taxes & fees
30 Nov - 1 Dec
The Grenada Suite Pool View Private Balcony

7. Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is £404
includes taxes & fees
18 Nov - 19 Nov
Tortuga Suite Sparkling Pool Hot Tub

8. The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
The price is £432
includes taxes & fees
30 Nov - 1 Dec
The Bartlum Luxury Studio In Prime Location

9. Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill
2.0 star property
Key West Historic District
The price is £352
includes taxes & fees
30 Nov - 1 Dec
Banana Split by Brightwild Pool Grill

10. New The Cottage at James House

New The Cottage at James House
2.0 star property
Key West Historic District
8.0 out of 10, Very good, (2 reviews)
"The best thing about this property is location. Short walk to everything - short walk to Sloppy Joes. It is overpriced for the accommodations but you pay for location. "
United States
Pamela
The price is £394
includes taxes & fees
17 Nov - 18 Nov
New The Cottage at James House

11. Mesa House Uno by Brightwild Perfect Location

Mesa House Uno by Brightwild Perfect Location
2.0 star property
Key West Historic District
The price is £434
includes taxes & fees
1 Dec - 2 Dec
Mesa House Uno by Brightwild Perfect Location

12. New Rose Petal Petite Suite - Pool Parking

New Rose Petal Petite Suite - Pool Parking
2.0 star property
Key West Historic District
The price is £329
includes taxes & fees
16 Nov - 17 Nov
New Rose Petal Petite Suite - Pool Parking

13. Poolside Retreat by Brightwild Cottage w Pool

Poolside Retreat by Brightwild Cottage w Pool
3.0 star property
Old Town Key West
2.0 out of 10, (2 reviews)
"My boyfriend and I booked this for our first anniversary together and I cannot stress enough to not book this listing. There was trash from people before us, back door was broken to get to the pool, air conditioning didn’t work (it was so hot inside that the glass was all fogged up it was like a sauna), and the blow dryer in the bathroom SHOCKED ME when I tried to plug it in, my boyfriend heard the sound of the shock loudly from two rooms away. Horrifying to say the least and when I reached out...
United States
Julia
The price is £337
includes taxes & fees
30 Nov - 1 Dec
Poolside Retreat by Brightwild Cottage w Pool

14. Sunnyside Up by Brightwild Pool Parking

Sunnyside Up by Brightwild Pool Parking
3.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
The price is £695
includes taxes & fees
18 Nov - 19 Nov
Sunnyside Up by Brightwild Pool Parking

15. Sea Breeze by Brightwild Off-street Parking

Sea Breeze by Brightwild Off-street Parking
2.0 star property
Old Town Key West
The price is £548
includes taxes & fees
30 Nov - 1 Dec
Sea Breeze by Brightwild Off-street Parking

16. Sky Loft by Brightwild Penthouse in Prime Spot

Sky Loft by Brightwild Penthouse in Prime Spot
2.0 star property
Old Town Key West
The price is £443
includes taxes & fees
18 Nov - 19 Nov
Sky Loft by Brightwild Penthouse in Prime Spot

17. Sweet Caroline by Brightwild Pool Parking

Sweet Caroline by Brightwild Pool Parking
2.0 star property
Key West Historic District
The price is £621
includes taxes & fees
15 Dec - 16 Dec
Sweet Caroline by Brightwild Pool Parking

18. Commodore s Cove by Brightwild Epic Location

Commodore s Cove by Brightwild Epic Location
2.0 star property
Key West Historic District
The price is £913
includes taxes & fees
14 Dec - 15 Dec
Commodore s Cove by Brightwild Epic Location

19. Cloud Suite on Duval Luxury Condo Epic Location

Cloud Suite on Duval Luxury Condo Epic Location
2.0 star property
Old Town Key West
8.0 out of 10, Very good, (1 review)
"Great space, amazing location, could be a bit cleaner. "
Canada
Marcus
The price is £704
includes taxes & fees
17 Nov - 18 Nov
Cloud Suite on Duval Luxury Condo Epic Location

20. Kamp by Brightwild Rooftop Penthouse On Duval

Kamp by Brightwild Rooftop Penthouse On Duval
2.0 star property
Old Town Key West
The price is £1,056
includes taxes & fees
21 Nov - 22 Nov
Kamp by Brightwild Rooftop Penthouse On Duval
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cow Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cow Key holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cow Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cow Key holiday rentals we have selected for you start as low as £228 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cow Key rentals

At Expedia, we put the best Cow Key holiday 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 holiday.

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 holiday rentals in Cow Key?

Yes, there are holiday rentals close to the most popular sights in Cow Key, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Cow Key has to offer?

Sugarloaf Key RV Resort & Cottages: This holiday home rental outside of Cow Key is located near a metro station, and offers an outdoor pool, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

What can I see and do in Cow Key?

Explore the area and family-friendly sights such as Florida Keys Eco - Discovery Center, or get out into nature at a spot like Florida Keys Beaches. In the wider area, you’ll find Duval Street and Key West Tropical Forest and Botanical Garden.

What are holiday rentals like in Cow Key?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Cow Key. Holiday rentals offer extras like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies packed with people while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental a great choice for family trips or small group gatherings.