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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Cow Key vacation rentals

A row of floating houses with balconies, connected by walkways, on calm 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, (201 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is AED 378
AED 1,053 total
includes taxes & fees
1 Nov - 2 Nov
Aqua Lodges at Hurricane Hole Marina
A waterfront property with a large building featuring balconies and a covered area, boats docked in front, and palm trees in the background.

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 AED 1,430
AED 2,502 total
includes taxes & fees
1 Nov - 2 Nov
Grand Marina Suite by Brightwild Waterfront
A deck with two white lounge chairs, a small round table, and a fire pit.

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 AED 1,903
AED 2,765 total
includes taxes & fees
13 Nov - 14 Nov
Lighthouse Suites Collection
A modern house with a swimming pool, a balcony, and a well-maintained garden.

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 AED 2,597
AED 4,391 total
includes taxes & fees
2 Nov - 3 Nov
Contra House Key West
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

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 AED 1,901
AED 3,585 total
includes taxes & fees
15 Nov - 16 Nov
Atlantic View Luxury Villa with Pool
A wooden boardwalk leading to a building with a green roof, surrounded by palm trees and a body of water.

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 AED 891
AED 2,043 total
includes taxes & fees
30 Nov - 1 Dec
The Grenada Suite Pool View Private Balcony
A dining area with a wooden table and chairs, a blue sofa, and a view of the outdoors through a glass door.

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 AED 2,519
AED 3,991 total
includes taxes & fees
22 Nov - 23 Nov
Sunnyside Up by Brightwild Pool Parking
A white two-story house with a balcony and a swimming pool.

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 AED 2,822
AED 5,720 total
includes taxes & fees
1 Nov - 2 Nov
Capmar House by Brightwild Huge Home Pool
A balcony with a wicker sofa and a palm tree, overlooking a street with buildings and a CVS store.

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 AED 1,789
AED 3,332 total
includes taxes & fees
2 Nov - 3 Nov
Duval Dream Loft by Brightwild Right on Duval
A wooden pedestrian bridge over a water body, surrounded by lush greenery and palm trees.

10. Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
The price is AED 910
AED 2,065 total
includes taxes & fees
1 Dec - 2 Dec
Tortuga Suite Sparkling Pool Hot Tub
A modern kitchen with a large island, built-in appliances, and pendant lighting.

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 AED 2,351
AED 3,917 total
includes taxes & fees
17 Nov - 18 Nov
Cloud Suite on Duval Luxury Condo Epic Location
A white house with a porch, surrounded by tropical plants and a stone pathway.

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 AED 1,362
AED 1,995 total
includes taxes & fees
2 Nov - 3 Nov
New The Cottage at James House
A spacious living area with a wooden dining table, comfortable seating, a flat-screen TV, and large windows offering a view of the outdoors.

13. Spindrift House by Brightwild Huge Pool Dock

Spindrift House by Brightwild Huge Pool Dock
2.0 star property
Raccoon Key
The price is AED 3,206
AED 6,152 total
includes taxes & fees
2 Nov - 3 Nov
Spindrift House by Brightwild Huge Pool Dock
A poolside area with lounge chairs, a wooden table, and palm trees.

14. The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
2.0 star property
Raccoon Key
The price is AED 4,705
AED 8,996 total
includes taxes & fees
1 Nov - 2 Nov
The Fairhaven House at Solaire Lunara Bay
A white two-story house with a central archway and a paved driveway.

15. Palmgale House in Key West

Palmgale House in Key West
2.5 star property
Raccoon Key
The price is AED 3,763
AED 7,705 total
includes taxes & fees
1 Nov - 2 Nov
Palmgale House in Key West
A cozy living area with a sofa, a dining table with chairs, and a television mounted on the wall.

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 AED 2,394
AED 4,776 total
includes taxes & fees
1 Dec - 2 Dec
Commodore s Cove by Brightwild Epic Location
A porch with a white railing, a pink door, and a white fence.

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 AED 918
AED 1,658 total
includes taxes & fees
29 Nov - 30 Nov
New Rose Petal Petite Suite - Pool Parking
A modern living room with a dark blue sectional sofa, a wooden coffee table, and a kitchen area with a blue backsplash and white cabinets.

18. Ebberly House by Brightwild Amazing Pool

Ebberly House by Brightwild Amazing Pool
2.0 star property
Raccoon Key
Ebberly House by Brightwild Amazing Pool
A poolside area with lounge chairs and umbrellas, a pool, and a view of the ocean.

19. New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House
2.0 star property
Raccoon Key
The price is AED 4,705
AED 8,996 total
includes taxes & fees
1 Nov - 2 Nov
New Waterfront Home - Dreamside House
A spacious kitchen with a large island, pendant lighting, and a dining area with a table and chairs.

20. New Windrose House by Brightwild Pool

New Windrose House by Brightwild Pool
2.0 star property
Raccoon Key
The price is AED 3,763
AED 7,705 total
includes taxes & fees
1 Nov - 2 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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

10/10 Excellent
"This property is very nice. The staff were excellent. I had an incident in which I couldn't get out of my car because of an issue with the electrical system. The head of security was able to walk me through what I needed to do before the police arrived. Thank you so much. I was panicking and he was able to calm me down. Thank you so much!!!"
Perla 3-night trip
Posted less than an hour ago
Blue Flamingo Resort Key West

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 Key West Tropical Forest and Botanical Garden.

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.