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

Our top choices for Cow Key holiday rentals

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (170)
"Location , staff , and aqua lodge were perfect."
United States
William
The price is AU$464
includes taxes & fees
18 Dec - 19 Dec
Aqua Lodges at Hurricane Hole Marina

Hyatt Vacation Club at Sunset Harbor, Key West

Hyatt Vacation Club at Sunset Harbor, Key West
3.5 star property
Old Town Key West
8.4 out of 10, Very good, (319)
"Place was great bed was comfy and the water was HOT!!! "
United States
Angela
The price is AU$507
includes taxes & fees
18 Dec - 19 Dec
Hyatt Vacation Club at Sunset Harbor, Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key
8.2 out of 10, Very good, (49)
"Great area. Quiet and comfortable "
United States
nancy c.
The price is AU$482
includes taxes & fees
16 Dec - 17 Dec
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
10.0 out of 10, Exceptional, (1)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
The price is AU$1,385
includes taxes & fees
16 Dec - 17 Dec
Atlantic View Luxury Villa with Pool

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.2 out of 10, Wonderful, (161)
"Great property,Great location. Will definitely stay there again."
United States
Roy F.
Cottage with Pool and Dockage, just minutes to Key West

Steps from Duval, Pool on Site & Bikes Included!

Steps from Duval, Pool on Site & Bikes Included!
Old Town Key West
9.6 out of 10, Exceptional, (412)
"Everything was excellent!"
United States
Susan L.
The price is AU$347
includes taxes & fees
11 Dec - 12 Dec
Steps from Duval, Pool on Site & Bikes Included!

DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (101)
"Great location. "
United States
Davian k.
The price is AU$661
includes taxes & fees
14 Dec - 15 Dec
DECEMBER SAVE 60% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Island Time #110 Ocean Views - Cudjoe Key

Island Time #110 Ocean Views - Cudjoe Key
2.5 star property
Cudjoe Key
9.6 out of 10, Exceptional, (11)
"Our family had an amazing vacation! We love the house and hope to come back!! "
United States
Tammy G.
The price is AU$989
includes taxes & fees
11 Dec - 12 Dec
Island Time #110 Ocean Views - Cudjoe Key

Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
2.0 star property
Stock Island
10.0 out of 10, Exceptional, (3)
"Nice place "
United States
Pawel
The price is AU$1,080
includes taxes & fees
15 Dec - 16 Dec
Grand Marina Suite by Brightwild Waterfront

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (49)
"The Post Card Point was absolutely stunning. Very clean and welcoming. Perfect access to fishing, diving, lobstering! Filet Table right on the water. We loved it :) will definitely be back!!!"
United States
Dave J.
The price is AU$1,384
includes taxes & fees
11 Dec - 12 Dec
Post Card Point #319 - Ocean Views!

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool
Cutthroat Harbor Estates
8.4 out of 10, Very good, (118)
"Great experience "
United States
Peyton S.
The price is AU$816
includes taxes & fees
11 Dec - 12 Dec
Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool
Cudjoe Key
9.8 out of 10, Exceptional, (143)
"Super relaxing! Great location! Wonderful views! "
United States
Allicia W.
The price is AU$1,452
includes taxes & fees
11 Dec - 12 Dec
Direct Oceanfront Cudjoe Key Escape 56' Dock, Ocean Views, Kayaks, Bikes & Pool

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly
Cudjoe Key
10.0 out of 10, Exceptional, (3)
"Beautiful "
United States
Lisa P.
The price is AU$1,503
includes taxes & fees
11 Dec - 12 Dec
Oceanfront Cudjoe Key Home - 35' Seawall, Sunrise Views, Pool & Pet-Friendly

DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!
Cudjoe Key
9.8 out of 10, Exceptional, (82)
"The place is clean and convenient for anyone wanting to spend time on the water in the keys"
United States
Ubaldo G.
The price is AU$1,086
includes taxes & fees
10 Jan - 11 Jan 2026
DECEMBER SAVE 60% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (109)
"Great value stay"
United States
Mike B.
The price is AU$426
includes taxes & fees
17 Dec - 18 Dec
SUGAR PALM STUDIO ~ Adult Only Studio w/Community Pool & Close to Town!

Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (152)
"This cottage served our purpose well, very close to our family’s home and was very clean and comfortable for a short stay."
United States
Richard S.
Cottage with Pool and Boat Dockage just minutes to Key West!

Palm - Beach Houses Key West

Palm - Beach Houses Key West
Upper Sugarloaf Key
10.0 out of 10, Exceptional, (14)
"Beautiful grounds and pool area. Enjoyed all the abundant wildlife as well as fishing from one of the piers."
United States
Harvey(Tabb) M.
Palm - Beach Houses Key West

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.4 out of 10, Exceptional, (95)
"Location is convenient, about a 15 minute walk go Duval Street so it’s in a nice and quiet area. The pictures are misleading, there is no central AC. "
United States
Priscilla
The price is AU$443
includes taxes & fees
17 Dec - 18 Dec
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

Resort View 1BR Suite With Direct Pool Access

Resort View 1BR Suite With Direct Pool Access
2.0 star property
Key West
The price is AU$562
includes taxes & fees
11 Dec - 12 Dec
Resort View 1BR Suite With Direct Pool Access

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
Stock Island
7.8 out of 10, Good, (26)
"This was exactly what was advertised, it was clean, and in a great location. The on-site restaurant had great food. Also, all staff members we encountered were very friendly and accommodating. I hope it’s available for our next trip."
United States
Julie
The price is AU$762
includes taxes & fees
11 Dec - 12 Dec
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!
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$347 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?

Spacious home with pool & balcony - 1 block from Duval Street: This holiday home rental outside of Cow Key is located in the city centre, and has a balcony, a BBQ and air conditioning 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.

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 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.