A sunset over a beach with a wooden pier and a small structure on it.

Holiday Rentals in Cow Key

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Our top choices for Cow Key holiday rentals

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.4 out of 10, Exceptional, (173 reviews)
"Great place "
United States
David
The price is €340
includes taxes & fees
15 Jul - 16 Jul
Cottage with Pool and Dockage, just minutes to Key West

SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JULY/AUG. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (93 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is €466
includes taxes & fees
14 Jul - 15 Jul
SAVE BIG $$$ JULY/AUG. OCEANFRONT 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, (192 reviews)
"The bathroom smelled a bit, but we loved the loft and the vibes of the houseboat. It’s hard to find 3 bedrooms at that reasonable price and we have 3 kids that do not want to sleep together so this was perfect. We ate at the bar and really enjoyed watching the jellyfish. It was a cool!"
United States
Emily
The price is €259
includes taxes & fees
16 Jul - 17 Jul
Aqua Lodges at Hurricane Hole Marina

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, (98 reviews)
"Perfect location. Privacy and comfort."
United States
Anthony
The price is €354
includes taxes & fees
1 Aug - 2 Aug
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (109 reviews)
"Enjoyed our stay at Venture Out. Loved having the water view. We used the pool, bikes and kayaks. Owners were very responsive. House was clean. Would definitely stay again."
United States
Lindsey S.
SAVE BIG $$$ JULY/AUG. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

47ft Viking Yacht · 2 Pools · Perry Marina · Key West

47ft Viking Yacht · 2 Pools · Perry Marina · Key West
Stock Island
7.6 out of 10, Good, (39 reviews)
"Perfect location! Had options of 2 pools to enjoy on property. The marina serves complimentary coffee. "
United States
Crystal A.
The price is €387
includes taxes & fees
21 Jul - 22 Jul
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

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, (161 reviews)
"This was our second stay here and just as we remembered. It was clean and we had everything we needed. Would recommend it for visiting Key West as its only a 30 minute drive in."
United States
John S.
The price is €521
includes taxes & fees
15 Jul - 16 Jul
Cudjoe Cottages, swimming pool, just 20 miles from Key West

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Relax at Keys Time – 2BR Waterfront Rental and Boat Dock
Cudjoe Key
9.2 out of 10, Wonderful, (30 reviews)
"Close to Key West and lots of great boating"
United States
Simon S.
The price is €559
includes taxes & fees
3 Aug - 4 Aug
Relax at Keys Time – 2BR Waterfront Rental and Boat Dock

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
9.4 out of 10, Exceptional, (26 reviews)
"Everything about our stay was simply wonderful. It was very Clean and quiet. It is in a very nice neighborhood and pet friendly. We loved the pool and the privacy. I will be back!"
United States
Marie
The price is €600
includes taxes & fees
14 Jul - 15 Jul
Spanish Queen @Venture Out, Cudjoe Key

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, (132 reviews)
"Great place to stay"
United States
walter l.
The price is €230
includes taxes & fees
14 Jul - 15 Jul
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Very clean, charming home. Host was fast with responses."
United States
April W.
The price is €587
includes taxes & fees
26 Jul - 27 Jul
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (101 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveller
Canal front, dockage, 2 bedroom, 2 bath

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
9.6 out of 10, Exceptional, (105 reviews)
"Not really close to much but a comfortable bed and clean room. The pool and grounds are lovely. Will stay again but rent a golf cart. "
United States
Laura T.
The price is €287
includes taxes & fees
10 Aug - 11 Aug
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

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

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (101 reviews)
"short drive to downtown of course as long as traffic allows it...quiet stay beautiful views...bring mosquito repellent. "
United States
Lismary D.
The price is €629
includes taxes & fees
22 Jul - 23 Jul
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Post Card Point #319 - Ocean Views!

Post Card Point #319 - Ocean Views!
Cudjoe Key
10.0 out of 10, Exceptional, (56 reviews)
"We loved our stay! Prime location"
United States
Lacey C.
Post Card Point #319 - Ocean Views!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cudjoe Key
9.6 out of 10, Exceptional, (14 reviews)
"All was excellent "
United States
Bryan M.
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Summer JULY Special@129 Sun. thru Wed. ngts.lodging Only 129. + extras.

Summer JULY Special@129 Sun. thru Wed. ngts.lodging Only 129. + extras.
Old Town Key West
9.0 out of 10, Wonderful, (196 reviews)
"Fantastic location! Close enough to walk to all the things, but very quiet and relaxing to hang out. Loved the back deck. Owner was very responsive and helpful. Neighbors were nice as well."
United States
Jeanine
The price is €292
includes taxes & fees
1 Aug - 2 Aug
Summer JULY Special@129 Sun. thru Wed. ngts.lodging Only 129. + extras.

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, (444 reviews)
"Great location! Close to everything! We biked everywhere and accommodations had everything we needed. "
United States
Richard A.
The price is €213
includes taxes & fees
14 Jul - 15 Jul
Steps from Duval, Pool on Site & Bikes Included!

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (31 reviews)
"This place was great! As advertised. It is located within a resort community, so it is safe with lots of amenities. "
United States
BRIAN S.
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
Cudjoe Key
9.6 out of 10, Exceptional, (53 reviews)
"Our stay was wonderful. Accommodations were as described and very comfortable. Location was great and the best views for the sunrise. "
United States
Kathy A.
The price is €756
includes taxes & fees
18 Jul - 19 Jul
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
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, apart-hotels, 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 €213 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?

Sugarloaf Key RV Resort & Cottages: This holiday home rental outside of Cow Key is located near a metro station, and offers an outdoor pool, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

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 Southernmost Point. While in the area, you can also visit popular places such as Duval Street and Mallory Square.

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.