Cow Key Holiday Rentals

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Holiday Rentals in Cow Key

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 NZ$614
per night
28 May - 29 May
Poolside Cottage #411
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
10.0 out of 10, Exceptional, (9)
"Sunset cruise was amazing around key west with captain lombardi"
SIGNIFICANTLY DISCOUNTED!! 45' Sea Ray Yacht Located in 5 Star Resort!
Outdoor dining
52' Power Catamaran Yacht at Luxury Resort Marina
10.0 out of 10, Exceptional, (11)
"We had a great time about Blue Jeans! Louie is an amazing host, as responsive as possible, also took us out for a cruise around Key West, AC works great! Easy Golf kart ride from the marina to down town key west. Pool at the marina was nice as well."
52' Power Catamaran Yacht at Luxury Resort Marina
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Pool
Bahama Village studio @ the Galleria!
10.0 out of 10, Exceptional, (5)
"It was very clean and nice. The air conditioning worked great. Located close to Duval. The only issue we had was that there was no closet or place to put clothes so after a few days it was hard to keep organized."
Bahama Village studio @ the Galleria!
Outdoor pool, a heated pool
Luxury 62' Yacht! In a Beautiful Resort
10.0 out of 10, Exceptional, (6)
"Everything was great and we would love to visit again!"
Luxury 62' Yacht! In a Beautiful Resort
Outdoor dining
Poolside Cottage #412
10.0 out of 10, Exceptional, (6)
"Perfect location. Poolside. Friendly staff, excellent service ~ Brandy!!!"
The price is NZ$614
per night
16 May - 17 May
Poolside Cottage #412
Interior
The Crystalmarine Suite – Rustic Luxury on the Sea
10.0 out of 10, Exceptional, (1)
"This was such a nice and cozy place to spend the weekend! We took our boat from key largo and docked up next to the houseboat and it was just amazing! I live how you can order food delivered to your door! It had tons of privacy and if your wondering no it does not move a lot at night! The solid pannel powered everything at night and we slept very peaceful! The sunsets from this house boat are 2nd to none would stay here again in the future!"
The price is NZ$1,159
per night
22 May - 23 May
The Crystalmarine Suite – Rustic Luxury on the Sea
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (189)
"The house location was absolutely amazing. Everything was top notch. I would recommend this house over and over again, the back yard is so tranquil and the layouts of the room worked out well for bigger parties."
The price is NZ$2,630
per night
19 May - 20 May
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Pool
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
9.8 out of 10, Exceptional, (257)
"This property and host exceeded all of our expectations. It was spacious, comfortable, and welcoming with its amazing kitchen, breezy rooms, and friendly neighbors. The hosts were a pleasure to work with and easy to reach whenever we wished to communicate with them. 10/10 would return to this property. I highly recommend it!"
Luxury High End, 2 Bikes, Highspeed Wi-Fi, Work station, Pool, Hot Tub, Gym
Property grounds
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (202)
"Fantastic property and location, our 2nd time there. Melanie, the host, is super responsive. I would highly recommend."
The price is NZ$734
per night
29 May - 30 May
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
Beach nearby
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
9.8 out of 10, Exceptional, (100)
"Beautiful property in a great location. I would definitely stay again."
The price is NZ$464
per night
16 May - 17 May
FLOR DE CANA ~ Adults Only, Poolview Suite in Azul Mansion!
A heated pool
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
9.8 out of 10, Exceptional, (103)
"Excellent top drawer"
Tom's Spectacular OceanFront 3 Bdrm Endless Atlantic view, Key West Amazing
Beach nearby
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
9.8 out of 10, Exceptional, (103)
"Quaint inn with a lovely “at home” feel. Great location close to downtown. The manager came every morning to fill a large water container with ice and sliced fruit. The pool was sparkling clean."
The price is NZ$466
per night
20 May - 21 May
CORONA ~ Adults Only, Historic Azul Mansion Suite with Community Pool!
Property grounds
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
9.8 out of 10, Exceptional, (79)
"Carpets were soiled, floors seemed not mopped and the refrigerator was dented."
Banana Breeze: Oceanview 4-bedroom home with private pool & lush landscaping!
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (330)
"First off the communication with Ken was amazing. Always got back to me right away. The property was very clean and just what was needed. Location. Was amazing and having the bikes was awesome. We rode them all over. Would definitely rent here again."
The price is NZ$398
per night
20 May - 21 May
Steps from Duval, Pool & Bikes $129-$299 Night!
Beach nearby
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
9.6 out of 10, Exceptional, (157)
"Couldn’t have asked for a better stay!! Comfy bed, quiet, great AC! Loved it all."
RIPTIDES ~Stylish Studio Located in a Central Location Near All the Action!
Property grounds
40'yacht in Paradise Awaits You!
9.6 out of 10, Exceptional, (23)
"We had a really nice couple of days on this boat. We are older (over 60), and we weren't sure if it was going to be our thing. It was good though! The host was amazingly helpful. We loved the private beach and pool right around the corner. We have been to Key West a lot, so we didn't need to do all the tourist stuff. We mostly stayed on Stock Island. It was easy to get Ubers, so we didn't bother with a car or golf cart. If we were staying longer, we probably would have rented a golf cart. The...
40'yacht in Paradise Awaits You!
Fridge, microwave, oven, stovetop
Cozy cottage with porch, WiFI, AC, & amazing walking locale - small dogs OK
9.4 out of 10, Exceptional, (199)
"Beautiful home, well equipped and close to everything. The bed was comfortable and the cottage was very clean. You can’t go wrong with this lovely place."
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, (24)
"Frank was freindly,knowlable and super accmodating. The facility was clean and close to everything we needed and far enough away from the noise...the locals where freindly and quiet. Just a great stay....WE WILL BE BACK!"
34’ Catamaran Sailboat
Property grounds
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
9.4 out of 10, Exceptional, (44)
"Wonderful place. We rented 7 bikes and were able to store them in the garage and ride wherever we needed to go. Didn’t need to go much since the place was so great, between the pool and the spacious open kitchen and decks we were able to cook and make cocktails."
Mother Ocean: Waterfront 4 Bedroom 3 Bath luxury Oceanfront home with pool
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.

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

View from property
Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
9.0 out of 10, Wonderful, (1510)
"Very nice property & highly recommend "
The price is NZ$373
per night
21 May - 22 May
Oceans Edge Key West Resort, Hotel & Marina
Outdoor pool, pool loungers
Havana Cabana at Key West - Adults Only
4.0 star property
8.8 out of 10, Excellent, (1449)
"Always a good place to stay. The accommodation worked well for our family. "
The price is NZ$346
per night
10 Jun - 11 Jun
Havana Cabana at Key West - Adults Only
Beach nearby, white sand
Margaritaville Beach House Key West
4.0 star property
8.6 out of 10, Excellent, (1752)
"Hotel was great venue."
The price is NZ$413
per night
15 May - 16 May
Margaritaville Beach House 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.

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 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.