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

Cow Key Holiday Rentals

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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 NZ$519
includes taxes & fees
4 Nov - 5 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 NZ$1,212
includes taxes & fees
4 Nov - 5 Nov
Grand Marina Suite by Brightwild Waterfront

3. Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
"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 NZ$1,337
includes taxes & fees
13 Nov - 14 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 NZ$2,123
includes taxes & fees
9 Nov - 10 Nov
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 NZ$1,733
includes taxes & fees
15 Nov - 16 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 NZ$990
includes taxes & fees
30 Nov - 1 Dec
The Grenada Suite Pool View Private Balcony

7. 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 NZ$1,701
includes taxes & fees
22 Nov - 23 Nov
Sunnyside Up by Brightwild Pool Parking

8. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is NZ$2,771
includes taxes & fees
4 Nov - 5 Nov
Capmar House by Brightwild Huge Home Pool

9. Duval Dream Loft by Brightwild Right on Duval

Duval Dream Loft by Brightwild Right on Duval
2.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
The price is NZ$1,842
includes taxes & fees
4 Nov - 5 Nov
Duval Dream Loft by Brightwild Right on Duval

10. Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is NZ$1,000
includes taxes & fees
1 Dec - 2 Dec
Tortuga Suite Sparkling Pool Hot Tub

11. 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 NZ$1,892
includes taxes & fees
17 Nov - 18 Nov
Cloud Suite on Duval Luxury Condo Epic Location

12. 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 NZ$973
includes taxes & fees
30 Nov - 1 Dec
New The Cottage at James House

13. Spindrift House by Brightwild Huge Pool Dock

Spindrift House by Brightwild Huge Pool Dock
2.0 star property
Raccoon Key
The price is NZ$3,777
includes taxes & fees
1 Dec - 2 Dec
Spindrift House by Brightwild Huge Pool Dock

14. The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is NZ$4,359
includes taxes & fees
4 Nov - 5 Nov
The Fairhaven House at Solaire Lunara Bay

15. Palmgale House in Key West

Palmgale House in Key West
2.5 star property
Raccoon Key
The price is NZ$3,733
includes taxes & fees
9 Nov - 10 Nov
Palmgale House in Key West

16. 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 NZ$2,530
includes taxes & fees
17 Nov - 18 Nov
Commodore s Cove by Brightwild Epic Location

17. 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 NZ$789
includes taxes & fees
29 Nov - 30 Nov
New Rose Petal Petite Suite - Pool Parking

18. Ebberly House by Brightwild Amazing Pool

Ebberly House by Brightwild Amazing Pool
2.0 star property
Raccoon Key
The price is NZ$3,725
includes taxes & fees
16 Nov - 17 Nov
Ebberly House by Brightwild Amazing Pool

19. New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House
2.0 star property
Raccoon Key
The price is NZ$4,359
includes taxes & fees
4 Nov - 5 Nov
New Waterfront Home - Dreamside House

20. New Windrose House by Brightwild Pool

New Windrose House by Brightwild Pool
2.0 star property
Raccoon Key
The price is NZ$3,725
includes taxes & fees
16 Nov - 17 Nov
New Windrose House by Brightwild Pool
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cow Key holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cow Key. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cow Key. Seeing all the best attractions is bound to make you fall in love with Cow Key. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cow Key short-term rentals, that won’t be hard to do.

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.