Cow Key Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Cow Key

Aqua Lodges at Hurricane Hole Marina
2.0 star property
8.8 out of 10, Excellent, (164)
"The stay was beautiful "
The price is AU$411
includes taxes & fees
16 Oct - 17 Oct
Aqua Lodges at Hurricane Hole Marina
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.0 out of 10, Wonderful, (51)
"We enjoyed our stay. Place is exactly as described. We really enjoyed the lanai. Wanted somewhere close to Key West and this turned out perfect. Would definitely stay here again. Thanks!"
The price is AU$544
includes taxes & fees
23 Oct - 24 Oct
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, (86)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
The price is AU$660
includes taxes & fees
15 Nov - 16 Nov
Canal front, dockage, 2 bedroom, 2 bath
Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
8.4 out of 10, Very good, (314)
"Great hotel with excellent location "
The price is AU$469
includes taxes & fees
30 Oct - 31 Oct
Hyatt Vacation Club at Sunset Harbor, Key West
Cottage with Pool and Dockage, just minutes to Key West
9.2 out of 10, Wonderful, (155)
"Stayed 13 days perfect location and this was our second stay at Cudjoe Cottages. Was able to dock boat here but had to put in at Cudjoe Gardens marina, just 5 minutes away. Basic old school Florida key’s cottages,clean and inexpensive. Nice community pool also. Definitely will stay again."
The price is AU$494
includes taxes & fees
16 Oct - 17 Oct
Cottage with Pool and Dockage, just minutes to Key West
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!
9.8 out of 10, Exceptional, (81)
"Great location near Key West. Awesome property, will book again."
The price is AU$691
includes taxes & fees
17 Oct - 18 Oct
OCEAN PARADISE AT VENTURE OUT + 4 BIKES & 2-2 PERSON KAYAKS! KING & QUEEN BEDS!
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
9.6 out of 10, Exceptional, (98)
"Clean place with room for 2 couples. Everything you need."
The price is AU$653
includes taxes & fees
19 Oct - 20 Oct
WATERFRONT PARADISE AT VENTURE OUT+4 BIKES & 2-2 SEAT KAYAKS! KING & QUEEN BEDS
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
2.0 star property
The price is AU$964
includes taxes & fees
17 Oct - 18 Oct
Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
9.8 out of 10, Exceptional, (237)
"Lovely property. Well equipped, nicely decorated, perfect for our stay."
The price is AU$1,274
includes taxes & fees
19 Oct - 20 Oct
Newly Remodeled! Gated Community on Open Water, Dock, Heated Pool, Kayaks, Bikes
Waterfront Luxury Home - Tidelands House
2.0 star property
The price is AU$4,419
includes taxes & fees
22 Oct - 23 Oct
Waterfront Luxury Home - Tidelands House
CORTEZ ~ Adults Only, Poolview King Room at Azul Mansion!
9.6 out of 10, Exceptional, (138)
"Great property. Lots of thoughtful amenities. Management friendly and responsive. "
The price is AU$356
includes taxes & fees
16 Oct - 17 Oct
CORTEZ ~ Adults Only, Poolview King Room at Azul Mansion!
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
The price is AU$968
includes taxes & fees
22 Oct - 23 Oct
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz
9.8 out of 10, Exceptional, (26)
"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"
The price is AU$1,124
includes taxes & fees
19 Oct - 20 Oct
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz
Island View 1BR Residence With Balcony
2.0 star property
10.0 out of 10, Exceptional, (1)
"The room was excellent, no complaints at all."
The price is AU$505
includes taxes & fees
20 Oct - 21 Oct
Island View 1BR Residence With Balcony
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
9.4 out of 10, Exceptional, (27)
"Close to Key West and lots of great boating"
The price is AU$958
includes taxes & fees
16 Oct - 17 Oct
Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
8.4 out of 10, Very good, (117)
"Deer in the front yard, perfect location, clean and friendly "
The price is AU$836
includes taxes & fees
17 Oct - 18 Oct
Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
7.8 out of 10, Good, (22)
"Loved everything about the stay, "
The price is AU$783
includes taxes & fees
30 Oct - 31 Oct
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
The Fairhaven House at Solaire Lunara Bay
2.0 star property
The price is AU$6,525
includes taxes & fees
31 Oct - 1 Nov
The Fairhaven House at Solaire Lunara Bay
New Waterfront Home - Dreamside House
2.0 star property
The price is AU$4,419
includes taxes & fees
22 Oct - 23 Oct
New Waterfront Home - Dreamside House
New Waterfront Home - Sunray House
2.0 star property
The price is AU$4,419
includes taxes & fees
22 Oct - 23 Oct
New Waterfront Home - Sunray 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Cow Key Hotel Reviews

Find out more about Cow Key

Everything you need to know about Cow Key holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cow Key holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cow Key holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Cow Key holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cow Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cow Key holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cow Key holiday rentals we have selected for you start as low as AU$349 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cow Key rentals

At Expedia, we put the best Cow Key holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cow Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cow Key holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cow Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Perfect Location, Private Heated Pool, Pristine Luxury Home!: This holiday home rental outside of Cow Key is located in the city centre, and has an outdoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

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 Stock Island Yacht Club & Marina.

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.