Cow Key Vacation Rentals

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Vacation Rentals in Cow Key

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

9.8 out of 10, Exceptional, (8)
"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"
$821 nightly
The price is $912
Jul 7 - Jul 8
Total includes taxes and fees
Stunning Ocean Views! 2BR Waterfront Home w/ Dock in Gated Keys Community

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

2.0 star property
9.4 out of 10, Exceptional, (3)
"Place was perfect for our trip. Staff was super nice and helpful as well. "
$770 nightly
The price is $854
Jul 12 - Jul 13
Total includes taxes and fees
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Post Card Point #319 - Ocean Views!

10.0 out of 10, Exceptional, (47)
"Really nice super clean & modern house with a great view. Lots of space. The community it’s in was very nice and quiet."
$750 nightly
The price is $833
Jul 19 - Jul 20
Total includes taxes and fees
Post Card Point #319 - Ocean Views!

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

9.4 out of 10, Exceptional, (6)
"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 !"
$578 nightly
The price is $641
Jul 9 - Jul 10
Total includes taxes and fees
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

9.6 out of 10, Exceptional, (94)
"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."
$479 nightly
The price is $532
Jul 23 - Jul 24
Total includes taxes and fees
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS

Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

2.5 star property
9.6 out of 10, Exceptional, (4)
"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. "
$556 nightly
The price is $617
Jul 7 - Jul 8
Total includes taxes and fees
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key

9.4 out of 10, Exceptional, (18)
"This is our second time staying at this property and everything was just as good as the first time!"
$617 nightly
The price is $685
Jul 14 - Jul 15
Total includes taxes and fees
Spanish Queen @Venture Out, Cudjoe Key

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

9.8 out of 10, Exceptional, (80)
"Great atmosphere, right on a canal. A perfect and comfortable home!"
$450 nightly
The price is $499
Jul 11 - Jul 12
Total includes taxes and fees
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!

Island Time #110 Ocean Views - Cudjoe Key

2.5 star property
9.6 out of 10, Exceptional, (5)
"We loved the property so much that we barely left it. The view from the porch was the most peaceful serene view. "
$560 nightly
The price is $621
Jul 8 - Jul 9
Total includes taxes and fees
Island Time #110 Ocean Views - Cudjoe Key

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

7.8 out of 10, Good, (12)
"Good experience. The property is well place and the Venture is really nice and quiet."
$463 nightly
The price is $513
Jul 7 - Jul 8
Total includes taxes and fees
Oceanview Paradise AT Venture Out+4 Bikes & 2-2 Seat Kayaks! King & Queen Beds!

Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock

9.8 out of 10, Exceptional, (235)
"We (family of 5) really enjoyed our stay. All the equipment was as listed and in great condition. The location was perfect if you're looking for a less hectic Florida Keys experience."
$780 nightly
The price is $866
Jul 7 - Jul 8
Total includes taxes and fees
Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes, Boat Dock

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

8.8 out of 10, Excellent, (84)
"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. "
$672 nightly
The price is $745
Jul 15 - Jul 16
Total includes taxes and fees
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Private and Exclusive Beach Getaway

10.0 out of 10, Exceptional, (1)
"If you're looking for a peaceful and picturesque getaway, the Bungalows at Sugarloaf Beach is the perfect choice!Thank you, Cadmier, for your hospitality. See again. Respectfully, Samat Sakebaev "
$1,985 nightly
The price is $2,205
Aug 6 - Aug 7
Total includes taxes and fees
Private and Exclusive Beach Getaway

The Lighthouse - Beach Houses Key West

9.6 out of 10, Exceptional, (11)
"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!"
$991 nightly
The price is $1,100
Aug 4 - Aug 5
Total includes taxes and fees
The Lighthouse - Beach Houses Key West

The Hemingway - Beach Houses Key West

9.8 out of 10, Exceptional, (7)
"Great place for our family of 5 A little off the beaten path which is exactly what we wanted Great host who answered all our questions promptly Sunrise and sunsets here were magnificent Great fishing off the dock as well"
$1,313 nightly
The price is $1,454
Aug 4 - Aug 5
Total includes taxes and fees
The Hemingway - Beach Houses Key West

Private and Exclusive Florida Keys Getaway

10.0 out of 10, Exceptional, (10)
"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!"
$895 nightly
The price is $993
Aug 4 - Aug 5
Total includes taxes and fees
Private and Exclusive Florida Keys Getaway

Parking Pool Dock - Shellstone House

2.0 star property
$3,249 nightly
The price is $3,655
Aug 3 - Aug 4
Total includes taxes and fees
Parking Pool Dock - Shellstone House

The Shellstone House at Solaire Lunara Bay

$2,732 nightly
The price is $3,031
Jul 15 - Jul 16
Total includes taxes and fees
The Shellstone House at Solaire Lunara Bay

New Waterfront Home - Dreamside House

2.0 star property
$3,286 nightly
The price is $3,697
Aug 3 - Aug 4
Total includes taxes and fees
New Waterfront Home - Dreamside House
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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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?

CAPTAIN'S QUARTERS ~ A Vintage Key West Retreat that is full of Charm!!: Visitors like this Cow Key vacation home rental. It is located in the city center and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and an oven, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

What can I see and do in Cow Key?

Explore the area and family-friendly sights such as Key West Shipwreck 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.