Cow Key Holiday Rentals

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Our top choices for Cow Key holiday rentals

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, (157 reviews)
"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.
The price is NZ$513
includes taxes & fees
31 Jan - 1 Feb
Cottage with Pool and Boat Dockage just minutes to 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
9.0 out of 10, Wonderful, (54 reviews)
"Clean rooms, clear guidelines, completely no contact experience without facing any trouble."
United States
Raj
The price is NZ$747
includes taxes & fees
2 Feb - 3 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cottage with swimming pool and dockage, just minutes to Key West!

Cottage with swimming pool and dockage, just minutes to Key West!
Cudjoe Key
9.0 out of 10, Wonderful, (163 reviews)
"Everything was there that I needed. Very nice area for my dog."
United States
Terry
The price is NZ$573
includes taxes & fees
15 Feb - 16 Feb
Cottage with swimming pool and dockage, just minutes to 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 review)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
Atlantic View Luxury Villa with Pool

Waterfront Home

Waterfront Home
Cudjoe Key
8.6 out of 10, Excellent, (176 reviews)
"Great location if you bring a boat. Secure location. Venture Out is a nice community. "
United States
Georgiana V.
The price is NZ$799
includes taxes & fees
6 Feb - 7 Feb
Waterfront Home

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (165 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
The price is NZ$624
includes taxes & fees
8 Feb - 9 Feb
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (102 reviews)
"Great location. "
United States
Davian k.
The price is NZ$916
includes taxes & fees
4 Feb - 5 Feb
SAVE BIG $$$ JANUARY! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (173 reviews)
"Unique place to stay! We loved the nature and the location! "
United States
Sara
The price is NZ$626
includes taxes & fees
4 Feb - 5 Feb
Aqua Lodges at Hurricane Hole Marina

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
9.0 out of 10, Wonderful, (92 reviews)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
United States
Jennifer D.
The price is NZ$802
includes taxes & fees
7 Feb - 8 Feb
Canal front, dockage, 2 bedroom, 2 bath

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 reviews)
"Nice place "
United States
Pawel
The price is NZ$1,675
includes taxes & fees
2 Feb - 3 Feb
Grand Marina Suite by Brightwild Waterfront

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 reviews)
"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 NZ$820
includes taxes & fees
1 Feb - 2 Feb
Viking Yacht Getaway in the Keys !!NEW LOCATION!! !!Tons of Amenities!!

The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (19 reviews)
"The perfect House , everything was good "
United States
CARLOS G.
The price is NZ$2,728
includes taxes & fees
3 Feb - 4 Feb
The Seagate Estate at Lunara Bay

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
8.6 out of 10, Excellent, (52 reviews)
"We were very happy with our stay. Everything was as expected or above. Old Keys vibe was exactly what we wanted. "
United States
Lauren R.
The price is NZ$744
includes taxes & fees
1 Feb - 2 Feb
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (19 reviews)
"This is our third time staying here. It is a great property and works perfectly for a three-person family."
United States
Kimberly G.
The price is NZ$1,118
includes taxes & fees
16 Feb - 17 Feb
Spanish Queen @Venture Out, Cudjoe Key

Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
9.8 out of 10, Exceptional, (40 reviews)
"Perfect, just perfect!"
United States
Mikael
The price is NZ$1,077
includes taxes & fees
12 Feb - 13 Feb
Living the Dream Key West Style

Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (41 reviews)
"Beautiful House, super clean, perfect location "
United States
carlos s.
The price is NZ$5,291
includes taxes & fees
11 Feb - 12 Feb
Suncoast House at Lunara Bay

Mastway House at Lunara Bay - Wellness Home

Mastway House at Lunara Bay - Wellness Home
Raccoon Key
9.6 out of 10, Exceptional, (32 reviews)
"The house was very clean and the neighborhood was in a perfect area and the neighbors were very friendly. Perfect get away!"
United States
Rachael S.
The price is NZ$3,764
includes taxes & fees
11 Feb - 12 Feb
Mastway House at Lunara Bay - Wellness Home

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (150 reviews)
"Boat access and docking spaces could be improved but overall not terrible. Spent a week here and enjoyed the stay. Quiet decent location. "
United States
bryan c.
The price is NZ$1,191
includes taxes & fees
6 Feb - 7 Feb
Cudjoe Cottages, swimming pool, just 20 miles from Key West

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

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (158 reviews)
"Great location , clear communications and listing accuracy. Will be coming back again "
United States
Kirk D.
The price is NZ$1,139
includes taxes & fees
15 Feb - 16 Feb
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"House was spotless. Pool lights blinked on and off all night but not a problem. "
United States
Emmett A.
The price is NZ$2,706
includes taxes & fees
1 Feb - 2 Feb
Capmar House at 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.
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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 favorite 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 depends 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 NZ$513 per night. Entering your travel dates in the search wizard you might find 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?

3-bedroom Yacht, Private Beach Yacht Club, sleeps 10, AC, Key West: This holiday home rental outside of Cow Key offers an outdoor pool, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. Make the most of garden 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 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.