Cow Key Vacation Rentals

Vacation Rentals in Cow Key

Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (331)
"My husband and I just got back from Key West. We had a fabulous time and loved where we stayed. Ken, the owner, is terrific. Great communication, excellent tips on things to do and places to eat. It a large house and you have a room to stay in with your own bathroom, small kitchen and bed. It was perfect for us. We will definitely be back next time we visit Key West. Thanks Ken for being a great host!!!"
The price is $99
$238 total
includes taxes & fees
30 May - 31 May
Steps from Duval, Pool & Bikes $129-$299 Night!
Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is $216
$366 total
includes taxes & fees
4 Jun - 5 Jun
Poolside Cottage #411
Sun loungers, beach towels
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
9.2 out of 10, Wonderful, (229)
"Great open communication with the property owner! Property located in quaint area of key west nearest Ram’s head restaurant, and the world famous blue heaven!!"
The price is $299
$578 total
includes taxes & fees
3 Jun - 4 Jun
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
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Beach nearby
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, (103)
"Beautiful property in a great location. I would definitely stay again."
The price is $121
$275 total
includes taxes & fees
30 May - 31 May
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
Pool | Outdoor pool, a heated pool
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (258)
"We really enjoyed our stay at this property. The condo was clean and well supplied with essentials. The property is well maintained and safe. We were able to use the included bicycles to get to most locations we wanted to go in old town. Southernmost point was a leisurely 15 min bike ride away. The property owner communicated well with us and answered all of our questions. The only thing we were not prepared for was the traffic noise. The unit does face a busy street, so you can hear vehicles...
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (192)
"This house was great. We had an amazing time. No complaints at all. It was walking distance to all the fun places. It was equipped with everything you need and the pool was an added plus. Cant say enough good things about it. The owner was also great to work with. We loved it!"
The price is $699
$1,520 total
includes taxes & fees
5 Jun - 6 Jun
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Restaurant
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (87)
"It’s an experience, it’s not a luxury stay. It’s sort of like staying in a camper with a septic holding tank that can get pretty smelly next to a working marina, with fish charters and a fish cleaning station. One morning we had to use a spare paddle to shoe away a stinky dead fish head so it wouldn’t get trapped under our unit and smell up the place. Staying on the water was unique but in mid May it would have been nice for more shade on the little deck. I’d save it for the slightly cooler...
The price is $123
$280 total
includes taxes & fees
2 Jun - 3 Jun
Aqua Lodges at Hurricane Hole Marina
Beach nearby
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
9.4 out of 10, Exceptional, (99)
"We loved it here. Great location and very clean. Would highly recommend if you are visiting key west."
The price is $116
$268 total
includes taxes & fees
30 May - 31 May
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
Fridge, microwave, coffee/tea maker, dining tables
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
9.2 out of 10, Wonderful, (94)
"We stayed for a long weekend and really enjoyed the Fontana Room at Azul Mansion. We were able to park on-site and check-in was very easy. It was walking distance to everything: Smathers Beach, the Southernmost Point, and Mallory Square. The pool was nice, and the amenities were great: fresh, cold water always available; Kuerig and pods in the room; plenty of towels including pool towels. Only downside was the pool lights shown into the room at night so room darkening curtains would be good. We...
The price is $117
$269 total
includes taxes & fees
3 Jun - 4 Jun
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
Beach nearby
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
9.8 out of 10, Exceptional, (56)
"Perfect, loved the pool area, very peaceful, beautiful property"
The price is $245
$497 total
includes taxes & fees
10 Jun - 11 Jun
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
Property grounds
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
8.8 out of 10, Excellent, (18)
"Good location as far walking distance to a Cuban food truck- Luna. Hogfish is a good restaurant, good seafood and good service, short walk. Property was clean. Beds comfortable. Mostly quiet. It’s about 3 miles from Key West."
ONE PARTICULAR HARBOR ~ Waterfront 2 BR/1 Ba w/ Hot Tub!
Property grounds
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (10)
"The Yacht was beautiful. The marina was amazing. The marina and resort had excellent restaurants and bars. It was very cool to see all of the boats coming and going. It was an easy Uber ride to Key West and enjoy the fast pace life. Then it was wonderful to come back to the quiet of the marina. Would highly recommend a stay here."
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
On the beach, sun loungers, beach towels
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
9.2 out of 10, Wonderful, (109)
"My husband and I visit Key West every year. We don’t go to frequent Duval Street we go for the warmth of the sun, artist fairs, sunsets, our favorite restaurants and our favorite shops. My husband does go fishing with the guys once or twice. But we come back and feel as though we’ve been in paradise. When your husband is a farmer it does really seem like paradise 😂"
GATED OCEANFRONT CONDO AT SMATHER'S BEACH
Property grounds
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
9.0 out of 10, Wonderful, (214)
"Very enjoyable"
Nassau Suite just steps to Duval Tropical oasis quiet location Downtown
A heated pool
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
10.0 out of 10, Exceptional, (54)
"My husband and I really enjoyed our time at Scarlet Mango Inn! Communication with the hosts was super easy with the convenience of reaching them via text. Our room was very clean and the property was so cute! It was a little noisy in the morning as staff cleaned outside, otherwise it was quiet. There is plenty to do within walking distance - food, bars, shopping, etc. We would definitely stay here again!"
The price is $164
$365 total
includes taxes & fees
30 May - 31 May
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
Beach nearby
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Pool
9.8 out of 10, Exceptional, (166)
"The property was in a great location. Two glitches when we arrived. We did not receive the code to get into the property and had to call at 4:00 to get it. Also, the sofa bed had not been made up and we could not find the sheets to make it up that night. Otherwise, the property was excellent and just as described on the website. These were minor annoyances and fairly easily resolved."
LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Pool
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (201)
"A very cozy little cottage in the heart of everything in Key West. In walking distance of everything, although bikes, golf carts and scooters are a great way to get around too. The front porch was nice to relax and sit on to finish out the day. Inside it was very clean, and had everything we needed for a short stay."
The price is $192
$478 total
includes taxes & fees
24 Jun - 25 Jun
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
Fridge, cookware/dishes/utensils, dining tables
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (25)
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
Beach nearby
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
9.6 out of 10, Exceptional, (159)
"In the center of it all."
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
Pool | A heated pool
Key West Beachfront Luxury 2/2 Condo A212
9.8 out of 10, Exceptional, (119)
"Nice property with great furnishings; really liked that it felt more like a residence than a resort. I would stay here again if I had the chance."
Key West Beachfront Luxury 2/2 Condo A212
Don't see what you're looking for?
See all available properties in Cow Key
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.

Cow Key Vacation Rental Travel Info

Number of vacation rentals
195
Known landmarks
Smathers Beach, South Beach and Fort Zachary Taylor Historic State Park
International airports
Miami, FL (MIA-Miami Intl.) and Key West, FL (EYW-Key West Intl.)

Other types of properties in Cow Key you may be interested in

6 outdoor pools, free cabanas, pool umbrellas
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1509)
"Excellent resort "
The price is $176
$257 total
includes taxes & fees
10 Jun - 11 Jun
Oceans Edge Key West Resort, Hotel & Marina
Beach nearby, white sand
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1767)
"Great hotel, I would come back anytime. "
The price is $229
$321 total
includes taxes & fees
4 Jun - 5 Jun
Margaritaville Beach House Key West
Outdoor pool, sun loungers
Havana Cabana at Key West
4.0 star property
8.8 out of 10, Excellent, (1464)
"We had an amazing time at Havana Cabana. The shuttle service was great. We hopped on the free bus Duval Loop at the drop off point. The staff was amazing. The pool was beautiful. Bar food outstanding. No complaints."
The price is $183
$270 total
includes taxes & fees
23 Jun - 24 Jun
Havana Cabana at Key West
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.

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 CNY717 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 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 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.

Recent reviews of Cow Key properties
Expedia 亿客行 verified reviews

The Gates Hotel Key West

The Gates Hotel Key West

5/5 Excellent
"Staff was helpful. Room was super clean. Bar and pool area amazing. Live entertainment was great. Easy access to all local happenings "
A verified traveler stayed at The Gates Hotel Key West
Posted 1 day ago
The Gates Hotel Key West