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

Cow Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Cow Key vacation rentals

A marina with boats docked, a small docked boat with a thatched roof, and a restaurant with outdoor seating overlooking the water.

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, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is ￥15,794
￥44,670 total
includes taxes & fees
Sep 24 - Sep 25
Aqua Lodges at Hurricane Hole Marina
A wooden boardwalk leading to a hotel with a green roof, surrounded by lush greenery and palm trees.

2. 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 ￥27,538
￥78,421 total
includes taxes & fees
Sep 24 - Sep 25
The Salt Cay | Updated! Stunning Sunset View, Pool
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

3. 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 ￥27,514
￥78,352 total
includes taxes & fees
Sep 27 - Sep 28
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
A wide sandy beach with palm trees and a clear sky.

4. 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 ￥39,363
￥64,182 total
includes taxes & fees
Sep 28 - Sep 29
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

5. 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 ￥33,271
￥81,162 total
includes taxes & fees
Sep 24 - Sep 25
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
A beach with a sailboat, palm trees, and beach chairs.

6. 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 traveler
The price is ￥77,884
￥97,532 total
includes taxes & fees
Sep 25 - Sep 26
Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
A resort pool area with lounge chairs and palm trees, surrounded by resort buildings.

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 ￥27,529
￥64,124 total
includes taxes & fees
Sep 24 - Sep 25
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

8. 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 ￥29,391
￥47,684 total
includes taxes & fees
Sep 27 - Sep 28
Island View 1BR Residence With Balcony
A hot tub with a view of a marina and boats during sunset.

9. 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 ￥50,339
￥62,766 total
includes taxes & fees
Oct 4 - Oct 5
Living the Dream Key West Style
A wide sandy beach with palm trees and a clear sky.

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
9.2 out of 10, Wonderful, (47 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
The price is ￥39,328
￥64,125 total
includes taxes & fees
Sep 24 - Sep 25
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
A beach with a sailboat, palm trees, and beach chairs.

11. 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
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

12. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (69 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 ￥26,215
￥46,713 total
includes taxes & fees
Sep 25 - Sep 26
Poolside Cottage #411
A beach with a sailboat, palm trees, and beach chairs.

13. 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.
The price is ￥71,592
￥89,667 total
includes taxes & fees
Sep 29 - Sep 30
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
A hotel room with a bed, a television on a dresser, a chair, and a window with curtains.

14. 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 ￥26,743
￥76,355 total
includes taxes & fees
Sep 24 - Sep 25
The Tortuga at Sunrise Suites - Balcony & Pool
A beach with a sailboat, palm trees, and beach chairs.

15. 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
A wooden deck with a large tree, outdoor seating, and a marina in the background.

16. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is ￥29,102
￥49,788 total
includes taxes & fees
Oct 18 - Oct 19
Poolside Cottage #412
A kitchen with wooden cabinets, a microwave, a stove, a refrigerator, and a toaster.

17. 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 ￥39,328
￥88,763 total
includes taxes & fees
Sep 27 - Sep 28
Grand Marina Suite - Poolside & Waterfront Condo

18. Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
The price is ￥44,185
￥82,802 total
includes taxes & fees
Oct 1 - Oct 2
Resort View 2BR Residence
A clear swimming pool surrounded by palm trees and lounge chairs.

19. 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
A modern living room with a sofa, coffee table, and a dining area with a table and chairs. There is a kitchen area with cabinets and appliances.

20. The Grand Cayman | Beautifully Remodeled Key West!

The Grand Cayman | Beautifully Remodeled Key West!
Key West
9.6 out of 10, Exceptional, (19 reviews)
"Great facility and loved the location! "
United States
Matt R.
The price is ￥27,538
￥78,421 total
includes taxes & fees
Sep 24 - Sep 25
The Grand Cayman | Beautifully Remodeled 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

Beachside Resort & Residences

Beachside Resort & Residences

8/10 Good
"Nice, spacious rooms. Nice Pool and fantastic bar tender! Maintenance speedy if needed. Nice to have the shuttle to/from downtown. Enjoyed our stay very much."
Karen 4-night trip
Posted 6 hours ago
Beachside Resort & Residences

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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Look no further and take a look at our great range of rental properties in Cow Key!

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?

Sugarloaf Key RV Resort & Cottages: Visitors like this Cow Key vacation home rental. It 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 vacation 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 larger area, you’ll find Duval Street and Robbie's.

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.