Cow Key Vacation Rentals

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Vacation Rentals in Cow Key

Aqua Lodges at Hurricane Hole Marina

2.0 star property
9.0 out of 10, Wonderful, (162)
"The stay was beautiful "
$244 nightly
The price is $275
Oct 8 - Oct 9
Total with taxes and fees
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

3.5 star property
8.4 out of 10, Very Good, (314)
"Great hotel with excellent location "
$276 nightly
The price is $310
Oct 27 - Oct 28
Total with taxes and fees
Hyatt Vacation Club at Sunset Harbor, Key West

Steps from Duval, Pool on Site & Bikes Included!

9.6 out of 10, Exceptional, (404)
"this was exactly as advertised and close to all the action"
$201 nightly
The price is $224
Oct 12 - Oct 13
Total with taxes and fees
Steps from Duval, Pool on Site & Bikes Included!

Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

8.8 out of 10, Excellent, (231)
"Property was cute and in a great location! "
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

10.0 out of 10, Exceptional, (22)
"We had a wonderful stay here with our kids. Can’t beat the location."
$279 nightly
The price is $309
Oct 8 - Oct 9
Total with taxes and fees
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!

Heart of Downtown Key West Cottage With Off-Street Parking

10.0 out of 10, Exceptional, (138)
"Great Location, Free Parking, comfortable beds"
Heart of Downtown Key West Cottage With Off-Street Parking

Perfect Location, Private Heated Pool, Pristine Luxury Home!

10.0 out of 10, Exceptional, (191)
"Outstanding place to stay, centrally located!"
$1,548 nightly
The price is $1,717
Oct 14 - Oct 15
Total with taxes and fees
Perfect Location, Private Heated Pool, Pristine Luxury Home!

Comfortable Condo with Pool, Private Balcony, & Beach Access

8.6 out of 10, Excellent, (135)
"Nice area, location, and wonderful apartment!"
$518 nightly
The price is $575
Oct 12 - Oct 13
Total with taxes and fees
Comfortable Condo with Pool, Private Balcony, & Beach Access

Coconut Mallory Resort And Marina By Kees Vacations

3.0 star property
8.2 out of 10, Very Good, (819)
"Great place really nice rooms"
Coconut Mallory Resort And Marina By Kees Vacations

TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

9.2 out of 10, Wonderful, (183)
"Great location; excellent property management "
TIDES ON SIMONTON ~ Perfectly located Condominium just off Duval!

Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

6.6 out of 10, (12)
"Unfortunately this stay was very disappointing. The marina was awesome. Tessa was awesome. The boat itself was disgusting. The pictures are very deceiving. What you see is not what you get. "
$293 nightly
The price is $325
Oct 15 - Oct 16
Total with taxes and fees
Charming 4-bedroom Yacht with AC, Pool, fitness room in fantastic Key West

1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools

$165 nightly
The price is $183
Oct 13 - Oct 14
Total with taxes and fees
1-bedroom boat at the Perry with AC, fitness room and 2 swimming pools

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

7.8 out of 10, Good, (22)
"Loved everything about the stay, "
$442 nightly
The price is $492
Oct 8 - Oct 9
Total with taxes and fees
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool!

9.6 out of 10, Exceptional, (18)
"Short walk to Duval street, quiet and very clean and comfortable."
$276 nightly
The price is $306
Nov 4 - Nov 5
Total with taxes and fees
GATO ROOM @ Inn on Fleming~ADULTS ONLY 2nd Floor Queen w/ Shared Heated Pool!

**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...

9.8 out of 10, Exceptional, (106)
"the condo was great roomingnice locationbeautiful, fun, great memories were made"
**RIVIERA AMERICANA @ THE BEACH** Ocean Views + LAST KEY SERVICES...

Living the Dream Key West Style

9.8 out of 10, Exceptional, (26)
"Great hosts and great accommodations!"
$292 nightly
The price is $326
Oct 8 - Oct 9
Total with taxes and fees
Living the Dream Key West Style

Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

9.6 out of 10, Exceptional, (17)
"Great place to stay! Very clean and steps to Duval Ave."
$309 nightly
The price is $341
Oct 9 - Oct 10
Total with taxes and fees
Holly's Hideaway - Truman @ Duval | Two-Bedroom Prime Location!

RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

9.6 out of 10, Exceptional, (189)
"Bucket list trip. Great location. Property was just what was expected. Perfect for 2!"
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!

Conch Republic Consul General's Cottage.-Historic District

9.4 out of 10, Exceptional, (164)
"Great host! Some minor issues but great for the price."
Conch Republic Consul General's Cottage.-Historic District

COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!

9.6 out of 10, Exceptional, (141)
"4th of July in Key West. Perfect girls trip. "
$212 nightly
The price is $236
Oct 8 - Oct 9
Total with taxes and fees
COHIBA ~ Adults Only, Poolview Queen Room in Historic Azul Mansion!
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

Find out more about Cow Key

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 $183 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.

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?

Perfect Location, Private Heated Pool, Pristine Luxury Home!: You might want to consider this vacation home rental near Cow Key, which is located in the city center and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Key West Tropical Forest and Botanical Garden. In the larger area, you’ll find Duval Street and Stock Island Yacht Club & Marina.

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.