Cow Key Holiday Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Cow Key

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

9.8 out of 10, Exceptional, (8)
"Great home base for fly fishing"
The price is AU$1,408
includes taxes & fees
25 July - 26 July
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
9.0 out of 10, Wonderful, (4)
"Place was perfect for our trip. Staff was super nice and helpful as well. "
The price is AU$1,306
includes taxes & fees
19 July - 20 July
Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Post Card Point #319 - Ocean Views!

10.0 out of 10, Exceptional, (47)
"Fantastic place, incredible view, great access to the Keys"
The price is AU$1,286
includes taxes & fees
22 July - 23 July
Post Card Point #319 - Ocean Views!

Galleon Getaway #533- Oceanfront Community

The price is AU$908
includes taxes & fees
17 July - 18 July
Galleon Getaway #533- Oceanfront Community

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

9.6 out of 10, Exceptional, (96)
"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."
The price is AU$821
includes taxes & fees
23 July - 24 July
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
9.0 out of 10, Wonderful, (6)
"A cozy, clean, and great stay in Cudjoe! Only 30 mins from Key West."
The price is AU$948
includes taxes & fees
21 July - 22 July
Blue Lobster Lodge - Venture Out #543 - Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key

9.4 out of 10, Exceptional, (18)
"We enjoyed our stay at venture out at the Spanish main residence it was lovely and we are going to return again next year"
The price is AU$1,058
includes taxes & fees
4 Aug - 5 Aug
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!"
The price is AU$859
includes taxes & fees
2 Aug - 3 Aug
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. "
The price is AU$953
includes taxes & fees
20 July - 21 July
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."
The price is AU$767
includes taxes & fees
17 July - 18 July
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."
The price is AU$1,351
includes taxes & fees
25 July - 26 July
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, (85)
"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. "
The price is AU$1,064
includes taxes & fees
20 July - 21 July
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Private and Exclusive Beach Getaway

10.0 out of 10, Exceptional, (10)
"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. "
The price is AU$2,668
includes taxes & fees
11 Aug - 12 Aug
Private and Exclusive Beach Getaway

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 "
The price is AU$2,975
includes taxes & fees
11 Aug - 12 Aug
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!"
The price is AU$1,630
includes taxes & fees
4 Aug - 5 Aug
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"
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!"
The price is AU$1,539
includes taxes & fees
4 Aug - 5 Aug
Private and Exclusive Florida Keys Getaway

Parking Pool Dock - Shellstone House

2.0 star property
The price is AU$6,748
includes taxes & fees
11 Aug - 12 Aug
Parking Pool Dock - Shellstone House

The Shellstone House at Solaire Lunara Bay

The price is AU$4,493
includes taxes & fees
20 July - 21 July
The Shellstone House at Solaire Lunara Bay
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

THE DELANEY HOUSE ~ NEW 4 BR/4 Ba Listing w/Pool & Parking in Prime Old Town!: This holiday home rental outside of Cow Key is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that 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 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.