Cow Key Holiday Rentals

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Holiday Rentals in Cow Key

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 NZ$400
per night
20 Jun - 21 Jun
Steps from Duval, Pool & Bikes $129-$299 Night!
Poolside Cottage #411
10.0 out of 10, Exceptional, (17)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is NZ$597
per night
12 Jun - 13 Jun
Poolside Cottage #411
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 NZ$943
per night
4 Jun - 5 Jun
Pet friendly 2/2. 4 free bikes. New renovation, heated pool 2 blocks to Duval St
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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 NZ$497
per night
2 Jun - 3 Jun
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
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
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 NZ$2,471
per night
5 Jun - 6 Jun
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (88)
"Everyone was extremely nice and helpful."
The price is NZ$442
per night
3 Jun - 4 Jun
Aqua Lodges at Hurricane Hole Marina
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 NZ$436
per night
4 Jun - 5 Jun
HAVANA VIEJA ~ Adults Only, Poolside 1 BR, 1 Ba w/ Shared Pool!
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 NZ$445
per night
3 Jun - 4 Jun
FONTANA ~ Adults Only, Pool Access Suite in Azul Mansion!
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 NZ$757
per night
6 Jun - 7 Jun
SUGAR PALM SUITE ~ Adult Only, Cozy 1 BR, 1 Ba w/ Kitchen and Shared Pool!
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!
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!
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
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
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 NZ$678
per night
18 Jun - 19 Jun
GOLDEN NUGGET ~ Adult Only, 1st Floor Queen Bedroom w/ Shared Pool!
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
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 NZ$777
per night
24 Jun - 25 Jun
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
34’ Catamaran Sailboat
9.4 out of 10, Exceptional, (25)
"Friendly, easy access and close to desired destination "
34’ Catamaran Sailboat
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
9.6 out of 10, Exceptional, (159)
"Lovely room. Very clean. Property mgt responded immediately when i had a request."
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
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
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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.

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

Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1511)
"Excellent resort "
The price is NZ$353
per night
6 Jun - 7 Jun
Oceans Edge Key West Resort, Hotel & Marina
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1770)
"Very convenient with all the amenities..... would recommend it to anyone "
The price is NZ$426
per night
4 Jun - 5 Jun
Margaritaville Beach House Key West
Havana Cabana at Key West
4.0 star property
8.8 out of 10, Excellent, (1466)
"Good place"
The price is NZ$296
per night
24 Jun - 25 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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cow Key holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cow Key. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cow Key. Seeing all the best attractions is bound to make you fall in love with Cow Key. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cow Key short-term rentals, that won’t be hard to do.

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?

Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!: This holiday home rental outside of Cow Key is equipped with 1 hot tub, air conditioning and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 wider area, you’ll find Duval Street and Robbie's.

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.

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