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

Cow Key Holiday Rentals

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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 NZ$209
includes taxes & fees
20 Sept - 21 Sept
Aqua Lodges at Hurricane Hole Marina

2. 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 NZ$529
includes taxes & fees
21 Sept - 22 Sept
Island View 1BR Residence With Balcony

3. The Butterfly Nest | Newly Updated w/ Shared Pool

The Butterfly Nest | Newly Updated w/ Shared Pool
Key West
9.8 out of 10, Exceptional, (48 reviews)
"Had a great time place is lovely "
United States
Sarah P.
The price is NZ$870
includes taxes & fees
20 Sept - 21 Sept
The Butterfly Nest | Newly Updated w/ Shared Pool

4. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (69 reviews)
"We stayed here for our honeymoon and it was perfect. The place was clean and well appointed. The pool right outside was huge and we spent lots of time there. Highly recommend!"
United States
DeAnna Z.
Poolside Cottage #411

5. 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, (35 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 NZ$845
includes taxes & fees
20 Sept - 21 Sept
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

6. 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 NZ$986
includes taxes & fees
20 Sept - 21 Sept
Grand Marina Suite - Poolside & Waterfront Condo

7. 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, (42 reviews)
"Great set up!!!"
United States
Benjamin
The price is NZ$711
includes taxes & fees
20 Sept - 21 Sept
47ft Viking Yacht · 2 Pools · Perry Marina · Key West

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 NZ$873
includes taxes & fees
23 Sept - 24 Sept
The Tortuga at Sunrise Suites - Balcony & Pool

9. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Very pleasant and generally a nice quiet community. "
United States
Julia M.
The price is NZ$517
includes taxes & fees
24 Sept - 25 Sept
Poolside Cottage #412

10. 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)
"I enjoyed my stay at the resort, highly recommend!"
United States
Michelaine a.
The price is NZ$718
includes taxes & fees
21 Sept - 22 Sept
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

11. SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
Old Town Key West
10.0 out of 10, Exceptional, (17 reviews)
"Great property in a great location right on Duval next to an incredible Rum bar. Highly recommend"
United States
darren s.
The price is NZ$503
includes taxes & fees
23 Sept - 24 Sept
SMUGGLER'S COVE ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

12. 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 NZ$537
includes taxes & fees
22 Sept - 23 Sept
Resort View 1BR Suite

13. Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Stock Island
9.6 out of 10, Exceptional, (136 reviews)
"I can't say enough about how wonderful this property is or the host."
United States
Linda
The price is NZ$902
includes taxes & fees
20 Sept - 21 Sept
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

14. The Saint Martin Suite | Delightfully Updated Beach Vibes!

The Saint Martin Suite | Delightfully Updated Beach Vibes!
Key West
9.8 out of 10, Exceptional, (16 reviews)
"We had a wonderful stay! The condo was very nice, clean, comfortable, spacious, well decorated and quiet. Parking was easy and communication with the host was excellent. Would definitely stay again!"
United States
Mark
The price is NZ$870
includes taxes & fees
20 Sept - 21 Sept
The Saint Martin Suite | Delightfully Updated Beach Vibes!

15. 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 NZ$712
includes taxes & fees
20 Sept - 21 Sept
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

16. Waterfront Dock Pool Condo Near Duval St Pet OK

Waterfront Dock Pool Condo Near Duval St Pet OK
Meadows
9.4 out of 10, Exceptional, (48 reviews)
"Hosts are super responsive and helpful. Perfect location. Would absolutely stay here again! "
United States
Amber G.
The price is NZ$615
includes taxes & fees
22 Sept - 23 Sept
Waterfront Dock Pool Condo Near Duval St Pet OK

17. 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, (457 reviews)
"Clean comfortable and close too many attractions."
United States
Mark A.
The price is NZ$411
includes taxes & fees
20 Sept - 21 Sept
Steps from Duval, Pool on Site & Bikes Included!

18. Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool
Old Town Key West
8.8 out of 10, Excellent, (56 reviews)
"The room was exactly what we expected, clean, cozy and a good place to chill after a day of adventuring in Key West. The pool/hot tub was wonderful and I wish I had one at home we didn’t want to leave and can’t wait to be back!"
United States
Cody S.
The price is NZ$573
includes taxes & fees
20 Sept - 21 Sept
Salvador's Seclusion | Cozy Studio Retreat w/ Heated Pool

19. The Saint Kitts Suite | Breathtaking View, Heated Pool

The Saint Kitts Suite | Breathtaking View, Heated Pool
Key West
9.8 out of 10, Exceptional, (8 reviews)
"Beautifully decorated and great location. The condo was clean, comfortable, quiet and well stocked. Would recommend and definitely stay there again!"
United States
Linda W.
The price is NZ$870
includes taxes & fees
20 Sept - 21 Sept
The Saint Kitts Suite | Breathtaking View, Heated Pool

20. The Barbados | Private Balcony, Pool View!

The Barbados | Private Balcony, Pool View!
Key West
9.8 out of 10, Exceptional, (11 reviews)
"Great trip"
United States
Doug P.
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Cow Key holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Cow Key. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Cow Key. Seeing all the best attractions is bound to make you fall in love with Cow Key. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Cow Key short-term rentals, that won’t be hard to do.

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 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.