Cow Key Vacation Rentals from ￥29,036: Search Short-Term Rentals

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Vacation Rentals in Cow Key

"Venture Out is a gated community in Cudjoe Key. The house was very clean and had everything you need to make yourself comfortable. We visited Key West which is about 30 minutes by car. Great place to stay"

￥118,399 total

includes taxes & fees

Jun 26 - Jun 27

"Place was perfect for our trip. Staff was super nice and helpful as well. "

￥122,182 total

includes taxes & fees

Jul 25 - Jul 26

"Really nice super clean & modern house with a great view. Lots of space. The community it’s in was very nice and quiet."

￥114,964 total

includes taxes & fees

Jul 1 - Jul 2

"The staff at Venture one was absolutely amazing. The home we stayed in was also a great location. Dated but clean. Definitely will stay at Venture again !"

￥92,904 total

includes taxes & fees

Jul 9 - Jul 10

"Really great, friendly community with lots of activities and a great view of the beach. Would definitely be on my list for another visit soon."

￥71,678 total

includes taxes & fees

Jun 29 - Jun 30

"The Blue Lobster is a gem. Clean, cute, enough room to spread out and every extra provided to make your stay comfortable. Community is friendly and has a nice pool, hot tubs and pickle ball courts. Loved it here. "

￥87,612 total

includes taxes & fees

Jun 26 - Jun 27

"This is our second time staying at this property and everything was just as good as the first time!"

￥99,211 total

includes taxes & fees

Jul 14 - Jul 15

"Great atmosphere, right on a canal. A perfect and comfortable home!"

￥72,845 total

includes taxes & fees

Jun 30 - Jul 1

"The house was lovely and the view outstanding. We had fun fishing, swimming, and talking to neighbors. Thank you for your hospitality. "

￥90,045 total

includes taxes & fees

Jul 8 - Jul 9

"Good experience. The property is well place and the Venture is really nice and quiet."

￥74,563 total

includes taxes & fees

Jul 7 - Jul 8

"The place was spacious, very clean and beautiful!"

￥101,809 total

includes taxes & fees

Jun 30 - Jul 1

"Property was adequate but could use a few updates. The location was great. Easy to get to Key West near good local restaurants and beaches. Would stay again. "

￥107,971 total

includes taxes & fees

Jun 30 - Jul 1

"I loved the secluded nature of the property it felt like we had the whole place to ourselves. Beach was beautiful and the property manager was very responsive. The location is close enough to Key West that it’s easy to do an excursion or go to dinner. "

￥278,999 total

includes taxes & fees

Jun 28 - Jun 29

"We saved up for 3 years for this trip and this property did not disappoint! Thank you for sharing your beautiful piece of paradise with us!"

￥231,481 total

includes taxes & fees

Jul 7 - Jul 8

"We had a great time at this out-of-the-way spot. It was quiet, beautiful, and comfortable. Lots to do around the property. The pool area is especially beautiful. Highly recommend!"

￥195,838 total

includes taxes & fees

Jul 3 - Jul 4

￥587,669 total

includes taxes & fees

Jul 15 - Jul 16

￥455,477 total

includes taxes & fees

Jul 13 - Jul 14

￥306,206 total

includes taxes & fees

Jul 15 - Jul 16

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Find out more about Cow Key

Search for holiday rentals in Cow Key on Expedia! You can easily find your home rentals, villas, holiday apartments in Cow Key using one of the methods below:

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Recent reviews of Cow Key properties

5/5 Excellent

"This is a wonderful resort in Key West that has great amenities and located on Duval Street! Highly recommend. "

A verified traveler stayed at Pier House Resort & Spa

Posted 15 hours ago

5/5 Excellent

"I loved everything about this hotel. All 3 restaurants on the property were GREAT!!!! Everything was clean and was even offered champagne upon arrival for check in. The morning wake up calls from the wild roosters were everything. I would definitely recommend anyone to stay here and it is family friendly. "

A verified traveler stayed at The Perry Hotel & Marina Key West

Posted 2 days ago

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All accommodation types in Cow Key

Apartments in Cow Key

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?

EL CORAZON~ Renovated Home w/ Direct Access to Duval St. w/ Pool & Parking!: Visitors like this Cow Key vacation home rental. It is located in the city center and offers a patio, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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.

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Cow Key Vacation Rentals

Check prices for these dates

Vacation Rentals in Cow Key

Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Post Card Point #319 - Ocean Views!

Reel Island Retreat #273 at Venture Out in the Florida Keys

WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key

OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Island Time #110 Ocean Views - Cudjoe Key

Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Private and Exclusive Beach Getaway

The Lighthouse - Beach Houses Key West

Private and Exclusive Florida Keys Getaway

Parking Pool Dock - Shellstone House

The Shellstone House at Solaire Lunara Bay

Mastway House by Brightwild Pool Dock

Waterfront Luxury Home - Tidelands House

Find out more about Cow Key

Recent reviews of Cow Key properties

Pier House Resort & Spa

Blue Flamingo Resort Key West

The Perry Hotel & Marina Key West

Havana Cabana at Key West

Beachside Resort & Residences

The Reach Key West, Curio Collection by Hilton

Margaritaville Beach House Key West

Courtyard by Marriott Key West Waterfront

Southernmost Beach Resort and Guesthouses

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Frequently asked questions