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

Cow Key Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

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, (200 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
$306 nightly
The price is $344
Oct 26 - Oct 27
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina
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.

2. The Grand Cayman | Beautifully Remodeled Key West!

The Grand Cayman | Beautifully Remodeled Key West!
Key West
9.8 out of 10, Exceptional, (21 reviews)
"Great facility and loved the location! "
United States
Matt R.
$447 nightly
The price is $497
Oct 26 - Oct 27
Total with taxes and fees
The Grand Cayman | Beautifully Remodeled Key West!
Exterior

3. 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
$325 nightly
The price is $365
Oct 27 - Oct 28
Total with taxes and fees
Island View 1BR Residence With Balcony
A wooden deck with a large tree, outdoor seating, and a marina in the background.

4. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
$271 nightly
The price is $301
Oct 18 - Oct 19
Total with taxes and fees
Poolside Cottage #412
A wooden boardwalk leading to a building with a green roof, surrounded by lush greenery and palm trees.

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

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (47 reviews)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
$447 nightly
The price is $497
Oct 26 - Oct 27
Total with taxes and fees
The Cat Island Suite | Charmingly Renovated w/ Pool
A wooden deck with outdoor seating, a large tree, and a marina with boats in the background.

6. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (70 reviews)
"I loved having the pool right outside the door! It was extremely clean and perfectly located for our needs. I really enjoyed sitting outside in the evenings. I would absolutely stay here again and recommend it to others!"
United States
Cristy D.
$275 nightly
The price is $305
Oct 18 - Oct 19
Total with taxes and fees
Poolside Cottage #411
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

7. 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.
$447 nightly
The price is $497
Oct 26 - Oct 27
Total with taxes and fees
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
A tropical garden pathway leading to a building with a yellow facade and green shutters.

8. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (138 reviews)
"Great place to stay"
United States
walter l.
$326 nightly
The price is $362
Oct 26 - Oct 27
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A wooden signpost with city names and distances in miles.

9. Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (459 reviews)
"This studio is in a wonderful location and comes with bikes and a pool spa. It is a fabulous place to stay for a relaxing get-away island-style."
United States
Laura D.
$215 nightly
The price is $239
Oct 19 - Oct 20
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!
A pool area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

10. Leo's Lodge | Newly Updated!

Leo's Lodge | Newly Updated!
Old Town Key West
9.0 out of 10, Wonderful, (35 reviews)
"Very nice place to stay, great pool area and great room. "
United States
Blake
$311 nightly
The price is $345
Oct 20 - Oct 21
Total with taxes and fees
Leo's Lodge | Newly Updated!
A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

11. AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!

AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
Old Town Key West
9.8 out of 10, Exceptional, (13 reviews)
"Friendly and clean place, love the look and location will be back"
United States
Amanda G.
$281 nightly
The price is $312
Oct 21 - Oct 22
Total with taxes and fees
AFTER HOURS ~ On Duval St, Adult Only, Adjoining Rum Bar & Nearby Beaches!
A tropical garden pathway leading to a building with a yellow facade and green shutters.

12. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (113 reviews)
"Not really close to much but a comfortable bed and clean room. The pool and grounds are lovely. Will stay again but rent a golf cart. "
United States
Laura T.
$268 nightly
The price is $298
Oct 20 - Oct 21
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A beach view with palm trees, a wooden pier, and a sunset over the water.

13. 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
$350 nightly
The price is $393
Oct 29 - Oct 30
Total with taxes and fees
Ocean Front 1BR Suite With Direct Beach Access
A multi-level wooden house with a blue staircase and white railings.

14. Underwater Cabana at Custom House Inn | On Duval!

Underwater Cabana at Custom House Inn | On Duval!
Key West Historic District
9.8 out of 10, Exceptional, (26 reviews)
"Perfect location, spacious room. Our second time staying at this venue."
United States
Colleen L.
$407 nightly
The price is $452
Oct 26 - Oct 27
Total with taxes and fees
Underwater Cabana at Custom House Inn | On Duval!
A hot tub with a view of a marina and boats during sunset.

15. 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.
$477 nightly
The price is $530
Oct 16 - Oct 17
Total with taxes and fees
Living the Dream Key West Style
A tranquil pond with a fountain in a park setting.

16. 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.
$497 nightly
The price is $552
Oct 18 - Oct 19
Total with taxes and fees
The Tortuga at Sunrise Suites - Balcony & Pool
A poolside area with a wooden deck, lounge chairs, and a staircase leading to a balcony.

17. VanGogh Studio | Updated, Old Town, Heated Pool

VanGogh Studio | Updated, Old Town, Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (57 reviews)
"Great crew here. From the airport shuttle to constant communication to make sure we were happy. Would highly recommend for a great getaway! Very convenient to lots of places to have fun."
United States
Jesse M.
$311 nightly
The price is $345
Oct 25 - Oct 26
Total with taxes and fees
VanGogh Studio | Updated, Old Town, Heated Pool
A courtyard with a gravel path, palm trees, and a building with a white facade.

18. Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval

Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval
Old Town Key West
9.8 out of 10, Exceptional, (51 reviews)
"Great location! Will stay here again."
United States
Stephanie
$375 nightly
The price is $416
Oct 21 - Oct 22
Total with taxes and fees
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval
A beach with lounge chairs, palm trees, and a water body.

19. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (35 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.
$511 nightly
The price is $567
Oct 18 - Oct 19
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
A swimming pool with lounge chairs and a thatched roof structure, surrounded by lush greenery and a brick patio.

20. 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, (137 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
$468 nightly
The price is $519
Oct 18 - Oct 19
Total with taxes and fees
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
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

10/10 Excellent
"A perfect get away place to stay for couples & families. Clean rooms, friendly staff & lots of great accommodations for everyone!"
David 4-night trip
Posted less than an 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 $220 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 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.