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

1. Aqua Lodges at Hurricane Hole Marina

Aqua Lodges at Hurricane Hole Marina
2.0 star property
Stock Island
8.8 out of 10, Excellent, (196 reviews)
"Unique stay on a boathouse! Clean place, plenty of room!"
United States
Kagni
The price is €238
includes taxes & fees
30 Aug - 31 Aug
Aqua Lodges at Hurricane Hole Marina

2. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (36 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is €258
includes taxes & fees
1 Sept - 2 Sept
Poolside Cottage #412

3. Island View 1BR Residence With Balcony

Island View 1BR Residence With Balcony
2.0 star property
Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great place it is a full apartment with everything you could need and very clean "
United States
Luis
The price is €260
includes taxes & fees
30 Aug - 31 Aug
Island View 1BR Residence With Balcony

4. The Cat Island Suite | Charmingly Renovated w/ Pool

The Cat Island Suite | Charmingly Renovated w/ Pool
Key West
9.8 out of 10, Exceptional, (47 reviews)
"I liked that it was pretty centrally located to everything very nice Thank you we had a great time "
United States
Patti E.
The price is €450
includes taxes & fees
28 Aug - 29 Aug
The Cat Island Suite | Charmingly Renovated w/ Pool

5. 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, (41 reviews)
"Great set up!!!"
United States
Benjamin
The price is €355
includes taxes & fees
30 Aug - 31 Aug
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

6. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (69 reviews)
"Excellent cottage in a quiet location. Our family of 4 enjoyed the stay & plan to return in the future!"
United States
Jennifer W.
The price is €277
includes taxes & fees
27 Sept - 28 Sept
Poolside Cottage #411

7. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (34 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
The price is €439
includes taxes & fees
28 Aug - 29 Aug
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

8. The Tortuga at Sunrise Suites - Balcony & Pool

The Tortuga at Sunrise Suites - Balcony & Pool
Key West
8.6 out of 10, Excellent, (30 reviews)
"We were very impressed with the grounds. Loved the pool area. Was extremely clean"
United States
Margaret G.
The price is €379
includes taxes & fees
30 Aug - 31 Aug
The Tortuga at Sunrise Suites - Balcony & Pool

9. The Grand Turk | Spectacular Sunset View, Private

The Grand Turk | Spectacular Sunset View, Private
Key West
9.0 out of 10, Wonderful, (19 reviews)
"Everything was clean, the beds were comfortable and it made our stay in Key West perfect!"
United States
Joy N.
The price is €422
includes taxes & fees
28 Aug - 29 Aug
The Grand Turk | Spectacular Sunset View, Private

10. Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.2 out of 10, Wonderful, (47 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
The price is €349
includes taxes & fees
1 Sept - 2 Sept
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

11. Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.2 out of 10, Wonderful, (115 reviews)
"Cute little place, host was very on top with communication."
United States
Michael L.
The price is €348
includes taxes & fees
1 Sept - 2 Sept
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

12. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (33 reviews)
"Pool was great! Just far enough from Duval street to get away and relax if needed or jump in the car and head down for live music! "
United States
Brent H.
The price is €463
includes taxes & fees
30 Aug - 31 Aug
Grand Marina Suite - Poolside & Waterfront Condo

13. Resort View 1BR Suite

Resort View 1BR Suite
2.0 star property
Key West
9.0 out of 10, Wonderful, (4 reviews)
"Open sewage behind pool bar rude front desk grumpy bartender Nice condo good restaurant "
United States
Michael
The price is €273
includes taxes & fees
2 Sept - 3 Sept
Resort View 1BR Suite

14. Waterfront Condo Dock Pool Near Duval St

Waterfront Condo Dock Pool Near Duval St
Meadows
9.8 out of 10, Exceptional, (29 reviews)
"Great stay! Beautiful view. No complaints. Easy check in and great communication with owner. Thanks for a great trip!"
United States
Haley P.
The price is €331
includes taxes & fees
2 Sept - 3 Sept
Waterfront Condo Dock Pool Near Duval St

15. 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, (451 reviews)
"Clean comfortable and close too many attractions."
United States
Mark A.
The price is €199
includes taxes & fees
7 Sept - 8 Sept
Steps from Duval, Pool on Site & Bikes Included!

16. Waterfront Condo | Pool, Dock, Parking, Sleeps 8

Waterfront Condo | Pool, Dock, Parking, Sleeps 8
Meadows
9.8 out of 10, Exceptional, (39 reviews)
"The location was geeat, easy to get to everything within minutes. "
United States
Brian G.
The price is €431
includes taxes & fees
8 Sept - 9 Sept
Waterfront Condo | Pool, Dock, Parking, Sleeps 8

17. Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30

Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30
Old Town Key West
9.0 out of 10, Wonderful, (198 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 €248
includes taxes & fees
31 Aug - 1 Sept
Aug.-Sept. Special@119.lodging Only 119. + extras. From.8-17 to 9-30

18. COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!
Old Town Key West
9.4 out of 10, Exceptional, (118 reviews)
"Excellent stay, great location! "
United States
Dr. Christopher S.
The price is €256
includes taxes & fees
30 Aug - 31 Aug
COCONUT PALM STUDIO ~ Adult Only Studio, Community Pool & Close to Town!

19. 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, (110 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The property was just as listed. Very clean, quiet, the pool was very refreshing! Great location, walkable to almost anything. Would highly recommend!"
United States
Chris & Sarah F.
The price is €256
includes taxes & fees
30 Aug - 31 Aug
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

20. The Barbados | Private Balcony, Pool View!

The Barbados | Private Balcony, Pool View!
Key West
9.6 out of 10, Exceptional, (10 reviews)
"Great trip"
United States
Doug P.
The price is €422
includes taxes & fees
28 Aug - 29 Aug
The Barbados | Private Balcony, Pool View!
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 €199 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 Mel Fisher Maritime Museum, or get out into nature at a spot like Florida Keys Beaches. 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.