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
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

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, (194 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
$246 nightly
The price is $277
Aug 18 - Aug 19
Total with taxes and fees
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
$290 nightly
The price is $327
Aug 17 - Aug 18
Total with taxes and fees
Island View 1BR Residence With Balcony
Luxury House, 2 Bedrooms, Pool View, Poolside | Premium bedding, iron/ironing board, WiFi (free), individually decorated

3. Lighthouse Suites Collection

Lighthouse Suites Collection
4.0 star property
Old Town Key West
$1,028 nightly
The price is $1,149
Aug 12 - Aug 13
Total with taxes and fees
Lighthouse Suites Collection
Condo | Living area | 32-inch Smart TV with satellite channels

4. Coconut Mallory Marina and Resort Condo

Coconut Mallory Marina and Resort Condo
3.0 star property
Key West
2.0 out of 10, (1 review)
"They did not have a room for me when i arrived. Said there was nothing they could do. I was left stranded and ended up paying twice the price for a worst room which was all I could find."
United States
Paris
$1,277 nightly
The price is $1,436
Aug 12 - Aug 13
Total with taxes and fees
Coconut Mallory Marina and Resort Condo
Exterior

5. 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
$1,181 nightly
The price is $1,328
Aug 12 - Aug 13
Total with taxes and fees
Contra House Key West
Exterior

6. 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
$925 nightly
The price is $1,041
Sep 9 - Sep 10
Total with taxes and fees
Atlantic View Luxury Villa with Pool
House | 1 bedroom

7. 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
$287 nightly
The price is $323
Aug 19 - Aug 20
Total with taxes and fees
Resort View 1BR Suite
House | 2 bedrooms

8. 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
$461 nightly
The price is $519
Aug 18 - Aug 19
Total with taxes and fees
Grand Marina Suite by Brightwild Waterfront
Exterior

9. 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
$451 nightly
The price is $508
Sep 9 - Sep 10
Total with taxes and fees
The Grenada Suite Pool View Private Balcony
House | 2 bedrooms, high-speed internet

10. Tortuga Suite Sparkling Pool Hot Tub

Tortuga Suite Sparkling Pool Hot Tub
2.0 star property
Key West
$455 nightly
The price is $512
Aug 31 - Sep 1
Total with taxes and fees
Tortuga Suite Sparkling Pool Hot Tub
House | Exterior

11. Ocean Front One Bedroom Residence

Ocean Front One Bedroom Residence
2.0 star property
Key West
$332 nightly
The price is $373
Aug 17 - Aug 18
Total with taxes and fees
Ocean Front One Bedroom Residence
House | Exterior

12. Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
$314 nightly
The price is $353
Aug 17 - Aug 18
Total with taxes and fees
Resort View 1BR Suite With Direct Pool Access
House | Exterior

13. Two Bedroom Residence With Balcony

Two Bedroom Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (1 review)
"The roosters crowing early morning was irritating "
United States
Catherine
$488 nightly
The price is $549
Aug 19 - Aug 20
Total with taxes and fees
Two Bedroom Residence With Balcony
Exterior

14. Ocean Front 1BR Suite With Direct Beach Access

Ocean Front 1BR Suite With Direct Beach Access
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Clean and spacious. Great view from room!"
United States
Jacqueline
$384 nightly
The price is $432
Aug 12 - Aug 13
Total with taxes and fees
Ocean Front 1BR Suite With Direct Beach Access
House | 2 bedrooms

15. Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
$506 nightly
The price is $569
Aug 17 - Aug 18
Total with taxes and fees
Resort View 2BR Residence
House | Exterior

16. Ocean Front 2BR Residence

Ocean Front 2BR Residence
2.0 star property
Key West
$361 nightly
The price is $406
Aug 19 - Aug 20
Total with taxes and fees
Ocean Front 2BR Residence
House | Terrace/patio

17. Banana Split by Brightwild Pool Grill

Banana Split by Brightwild Pool Grill
2.0 star property
Key West Historic District
$348 nightly
The price is $392
Aug 18 - Aug 19
Total with taxes and fees
Banana Split by Brightwild Pool Grill
House | Exterior

18. Resort View 3BR Residence

Resort View 3BR Residence
2.0 star property
Key West
$767 nightly
The price is $863
Aug 19 - Aug 20
Total with taxes and fees
Resort View 3BR Residence
Garden

19. 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
$314 nightly
The price is $354
Aug 17 - Aug 18
Total with taxes and fees
New The Cottage at James House
House | 1 bedroom, high-speed internet

20. The Bartlum Luxury Studio In Prime Location

The Bartlum Luxury Studio In Prime Location
2.0 star property
Key West Historic District
$326 nightly
The price is $366
Aug 31 - Sep 1
Total with taxes and fees
The Bartlum Luxury Studio In Prime Location
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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"We loved the location. The view was nice. The room had a couple of issues, the shower had to be washed out after our arrival, there were some hairs in the shower, and the ceiling fan light would cut on and off on its own during the night, waking us up. The pool areas were nice, but the bar closed down early when people were still out enjoying the pool. The food from the cafe was great, enjoyed breakfast and snacks from there. Overall the staff was good."
Amanda 4-night trip
Posted 1 hour ago
Southernmost Beach Resort and Guesthouses

Find out more about Cow Key

Everything you need to know about Cow Key vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cow Key vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cow Key vacation 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 low season months. For more hustle and bustle, you may prefer to visit Cow Key in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $227 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cow Key rentals

At Expedia, we put the best Cow Key vacation 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 vacation.

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.

Explore a world of travel with Expedia

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 Mel Fisher Maritime 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.