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

Cow Key Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Cow Key vacation rentals

Front of property

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, (193 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
The price is AED 401
AED 1,067 total
includes taxes & fees
31 Jul - 1 Aug
Aqua Lodges at Hurricane Hole Marina
House | Exterior

2. 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 AED 787
AED 1,215 total
includes taxes & fees
30 Aug - 31 Aug
Island View 1BR Residence With Balcony
Pool

3. 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 AED 1,543
AED 1,904 total
includes taxes & fees
1 Aug - 2 Aug
Living the Dream Key West Style
Property grounds

4. The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (45 reviews)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
The price is AED 719
AED 1,906 total
includes taxes & fees
1 Aug - 2 Aug
The Cat Island Suite | Charmingly Renovated w/ Pool
Outdoor pool

5. 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, (39 reviews)
"Great stay and an excellent host! "
United States
Mike T.
The price is AED 643
AED 1,516 total
includes taxes & fees
3 Aug - 4 Aug
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Property grounds

6. 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, (33 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 AED 719
AED 1,946 total
includes taxes & fees
2 Aug - 3 Aug
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Living area

7. The Grand Cayman | Beautifully Remodeled Key West!

The Grand Cayman | Beautifully Remodeled Key West!
Key West
9.6 out of 10, Exceptional, (19 reviews)
"Very clean and modern units with all of the amenities. Very comfortable for the 5 of us. Nice pool area and convenient to all sites. Shuttle service to Ferry terminal was excellent benefit"
United States
Israel
The price is AED 760
AED 2,015 total
includes taxes & fees
7 Aug - 8 Aug
The Grand Cayman | Beautifully Remodeled Key West!
Beach nearby

8. 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 AED 1,010
AED 1,623 total
includes taxes & fees
2 Aug - 3 Aug
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Beach nearby, beach towels

9. 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)
"Cute little place, host was very on top with communication."
United States
Michael L.
The price is AED 1,010
AED 1,630 total
includes taxes & fees
3 Aug - 4 Aug
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Outdoor dining

10. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (68 reviews)
"We had a wonderful stay. The house was very clean, the area was quiet and peaceful, and the pool was incredibly relaxing. We enjoyed it so much that we have already booked another stay."
United States
Tiara B.
Poolside Cottage #411
Beach

11. 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 AED 1,359
AED 1,724 total
includes taxes & fees
10 Aug - 11 Aug
Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
House | 1 bedroom

12. Resort View 1BR Suite

Resort View 1BR Suite
2.0 star property
Key West
9.0 out of 10, Wonderful, (4 reviews)
"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "
United States
Michael
The price is AED 802
AED 1,232 total
includes taxes & fees
30 Aug - 31 Aug
Resort View 1BR Suite
Pool

13. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (32 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 AED 922
AED 2,077 total
includes taxes & fees
25 Aug - 26 Aug
Grand Marina Suite - Poolside & Waterfront Condo
Outdoor dining

14. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (36 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is AED 612
AED 1,104 total
includes taxes & fees
11 Aug - 12 Aug
Poolside Cottage #412
TV, offices

15. 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 AED 503
AED 1,665 total
includes taxes & fees
24 Aug - 25 Aug
The Tortuga at Sunrise Suites - Balcony & Pool
Beach nearby

16. 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 AED 1,234
AED 1,547 total
includes taxes & fees
25 Aug - 26 Aug
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
Beach nearby

17. 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.
The price is AED 2,073
AED 2,630 total
includes taxes & fees
6 Aug - 7 Aug
Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Pool

18. Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (38 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
The price is AED 1,098
AED 2,287 total
includes taxes & fees
2 Aug - 3 Aug
Paradise found
Beach

19. Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking

Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking
Key West
9.0 out of 10, Wonderful, (138 reviews)
"Clean with very good furnishings."
United States
Allen J.
The price is AED 2,073
AED 2,630 total
includes taxes & fees
3 Aug - 4 Aug
Completely Renovated Condo with Pool, Hot Tub, & Private Patio - Free Parking
Living area

20. The Saint Martin Suite | Delightfully Updated Beach Vibes!

The Saint Martin Suite | Delightfully Updated Beach Vibes!
Key West
9.8 out of 10, Exceptional, (15 reviews)
"Very clean unit, comfortable beds, helpful customer service and convenient shuttle with great driver!"
United States
Diane H.
The price is AED 760
AED 1,989 total
includes taxes & fees
28 Aug - 29 Aug
The Saint Martin Suite | Delightfully Updated Beach Vibes!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cow Key Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"The private beach is truly superior. A classic Key West resort perfectly located and very quiet."
Jean 6-night trip
Posted 2 hours ago
Pier House Resort & Spa

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 Key West Shipwreck Museum, 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.