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

Cow Key Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Cow Key holiday 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, (202 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is HK$1,263
HK$2,779 total
includes taxes & fees
16 Nov - 17 Nov
Aqua Lodges at Hurricane Hole Marina
A pool area with a wooden deck, lounge chairs, and a waterfall feature.

2. Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
10.0 out of 10, Exceptional, (2 reviews)
"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 HK$4,064
HK$5,905 total
includes taxes & fees
13 Nov - 14 Nov
Lighthouse Suites Collection
A beachside resort with a wooden deck, palm trees, and a sunset view.

3. 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 HK$3,054
HK$5,342 total
includes taxes & fees
15 Nov - 16 Nov
Grand Marina Suite by Brightwild Waterfront
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 HK$5,545
HK$9,375 total
includes taxes & fees
8 Dec - 9 Dec
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 HK$4,059
HK$7,654 total
includes taxes & fees
17 Nov - 18 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 HK$1,902
HK$4,363 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 HK$4,206
HK$7,203 total
includes taxes & fees
17 Nov - 18 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 HK$8,094
HK$14,541 total
includes taxes & fees
16 Nov - 17 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 HK$4,944
HK$8,378 total
includes taxes & fees
30 Nov - 1 Dec
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 HK$1,942
HK$4,409 total
includes taxes & fees
1 Dec - 2 Dec
Tortuga Suite Sparkling Pool Hot Tub
A white house with a porch, surrounded by tropical plants and a stone pathway.

11. 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 HK$2,849
HK$4,193 total
includes taxes & fees
1 Dec - 2 Dec
New The Cottage at James House
A modern kitchen with a large island, built-in appliances, and pendant lighting.

12. 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 HK$3,854
HK$7,054 total
includes taxes & fees
17 Nov - 18 Nov
Cloud Suite on Duval Luxury Condo Epic Location
A modern kitchen with white cabinets, stainless steel appliances, and a wooden door.

13. The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
The price is HK$2,506
HK$4,648 total
includes taxes & fees
23 Nov - 24 Nov
The Bartlum Luxury Studio In Prime Location
A cozy living area with a sofa, a dining table with chairs, and a television mounted on the wall.

14. 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 HK$4,761
HK$9,804 total
includes taxes & fees
1 Dec - 2 Dec
Commodore s Cove by Brightwild Epic Location
A spacious living area with a wooden dining table, comfortable seating, a flat-screen TV, and large windows offering a view of the outdoors.

15. Spindrift House by Brightwild Huge Pool Dock

Spindrift House by Brightwild Huge Pool Dock
2.0 star property
Raccoon Key
The price is HK$9,731
HK$16,383 total
includes taxes & fees
30 Nov - 1 Dec
Spindrift House by Brightwild Huge Pool Dock
A white two-story house with a central archway and a paved driveway.

16. Palmgale House in Key West

Palmgale House in Key West
2.5 star property
Raccoon Key
The price is HK$10,382
HK$19,091 total
includes taxes & fees
8 Dec - 9 Dec
Palmgale House in Key West
A spacious living area with a large sofa, a coffee table, and a view of a balcony with a railing.

17. Mastway House by Brightwild Pool Dock

Mastway House by Brightwild Pool Dock
2.0 star property
Raccoon Key
The price is HK$8,790
HK$15,323 total
includes taxes & fees
17 Nov - 18 Nov
Mastway House by Brightwild Pool Dock
A spacious kitchen with modern appliances, a dining area with a wooden table and chairs, and a view of a lake through large windows.

18. Springtide House by Brightwild Waterfront Pool

Springtide House by Brightwild Waterfront Pool
2.0 star property
Raccoon Key
Springtide House by Brightwild Waterfront Pool
A porch with a white railing, a pink door, and a white fence.

19. 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 HK$1,810
HK$3,371 total
includes taxes & fees
29 Nov - 30 Nov
New Rose Petal Petite Suite - Pool Parking
A spacious living area with a blue sofa, a grey armchair, and a wooden coffee table. Large sliding glass doors lead to a pool and outdoor furniture.

20. Suncoast House by Brightwild Pool Boat Dock

Suncoast House by Brightwild Pool Boat Dock
2.0 star property
Raccoon Key
The price is HK$6,846
HK$14,471 total
includes taxes & fees
23 Nov - 24 Nov
Suncoast House by Brightwild Pool Boat Dock
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

The Southernmost Inn - Adults Only

The Southernmost Inn - Adults Only

10/10 Excellent
"Perfect location"
Amy 3-night trip
Posted 3 hours ago
The Southernmost Inn - Adults Only

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 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.