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. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is £223
includes taxes & fees
6 Oct - 7 Oct
Island View 1BR Residence With Balcony

2. Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (62 reviews)
"Great would definitely stay again "
United States
Zach C.
The price is £310
includes taxes & fees
2 Oct - 3 Oct
Living the Dream Key West Style

3. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (198 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is £205
includes taxes & fees
7 Oct - 8 Oct
Aqua Lodges at Hurricane Hole Marina

4. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (35 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
The price is £374
includes taxes & fees
6 Oct - 7 Oct
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

5. The Salt Cay | Updated! Stunning Sunset View, Pool

The Salt Cay | Updated! Stunning Sunset View, Pool
Key West
9.6 out of 10, Exceptional, (59 reviews)
"Everything was amazing! My family and I enjoyed every part of our stay; 10 out of 10 would recommend :)"
United States
Rebecca H.
The price is £386
includes taxes & fees
14 Oct - 15 Oct
The Salt Cay | Updated! Stunning Sunset View, Pool

6. Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.2 out of 10, Wonderful, (115 reviews)
"I enjoyed my stay at the resort, highly recommend!"
United States
Michelaine a.
The price is £352
includes taxes & fees
3 Oct - 4 Oct
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

7. 47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.6 out of 10, Good, (42 reviews)
"Great set up!!!"
United States
Benjamin
The price is £380
includes taxes & fees
2 Oct - 3 Oct
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

8. Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Key West
9.4 out of 10, Exceptional, (122 reviews)
"We loved the location."
United States
Aneesah D.
Sunny Condo with WiFi, Hot Tub, Pool & Tennis

9. Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking

Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
Key West
9.0 out of 10, Wonderful, (144 reviews)
"Easy check in. Accommodations were very good as advertised. "
United States
Anonymous traveller
Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking

10. Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (49 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
The price is £352
includes taxes & fees
3 Oct - 4 Oct
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

11. Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
The price is £403
includes taxes & fees
5 Oct - 6 Oct
Resort View 2BR Residence

12. Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (39 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
Paradise found

13. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (136 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
The price is £478
includes taxes & fees
7 Oct - 8 Oct
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

14. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (70 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is £225
includes taxes & fees
14 Oct - 15 Oct
Poolside Cottage #411

15. Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
Key West
8.8 out of 10, Excellent, (218 reviews)
"The two bedroom apartment offered everything we needed, and the pool and hot tub were welcome additions. We liked that it was close to the airport."
United States
Ann A.
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

16. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (33 reviews)
"Pool was great! Just far enough from Duval street to get away and relax if needed or jump in the car and head down for live music! "
United States
Brent H.
The price is £481
includes taxes & fees
12 Oct - 13 Oct
Grand Marina Suite - Poolside & Waterfront Condo

17. Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking

Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking
Key West
8.8 out of 10, Excellent, (124 reviews)
"Great location!"
United States
Rodney W.
Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking

18. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Definitely would stay here again. Very smooth process. Property was perfect for our family of 5. We loved having access to the pool right at our doorstep. Very accurate photos and description. Excellent value for the money."
United States
Danielle D.
The price is £233
includes taxes & fees
10 Oct - 11 Oct
Poolside Cottage #412

19. Aquaria House at Lunara Bay

Aquaria House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"Loved the property and the location!! It was perfect for me and the family. Short commute to everything we needed and wanted. I can't wait to go back for the next visit!!"
United States
Chris H.
The price is £1,085
includes taxes & fees
11 Oct - 12 Oct
Aquaria House at Lunara Bay

20. The Tortuga at Sunrise Suites - Balcony & Pool

The Tortuga at Sunrise Suites - Balcony & Pool
Key West
8.6 out of 10, Excellent, (30 reviews)
"We were very impressed with the grounds. Loved the pool area. Was extremely clean"
United States
Margaret G.
The price is £378
includes taxes & fees
27 Oct - 28 Oct
The Tortuga at Sunrise Suites - Balcony & 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

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 £202 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.