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

Cow Key Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Cow Key vacation rentals

Front of property

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 ￥15,750
￥44,547 total
includes taxes & fees
Sep 24 - Sep 25
Aqua Lodges at Hurricane Hole Marina
Property grounds

2. The Salt Cay | Updated! Stunning Sunset View, Pool

The Salt Cay | Updated! Stunning Sunset View, Pool
Key West
9.6 out of 10, Exceptional, (59 reviews)
"Everything was amazing! My family and I enjoyed every part of our stay; 10 out of 10 would recommend :)"
United States
Rebecca H.
The price is ￥27,266
￥77,924 total
includes taxes & fees
Sep 24 - Sep 25
The Salt Cay | Updated! Stunning Sunset View, Pool
Property grounds

3. 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 ￥27,266
￥77,767 total
includes taxes & fees
Sep 23 - Sep 24
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Beach nearby, beach towels

4. 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 ￥39,220
￥63,949 total
includes taxes & fees
Sep 28 - Sep 29
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Outdoor pool, a heated pool

5. 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 ￥33,180
￥80,784 total
includes taxes & fees
Sep 23 - Sep 24
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS
Beach

6. Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking

Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
Key West
9.0 out of 10, Wonderful, (144 reviews)
"Easy check in. Accommodations were very good as advertised. "
United States
Anonymous traveler
The price is ￥77,671
￥97,265 total
includes taxes & fees
Sep 25 - Sep 26
Sunrise Suites Condo with Balcony - Shared Pool, Hot Tub, Tennis, Free Parking
Outdoor pool

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 ￥27,454
￥63,949 total
includes taxes & fees
Sep 23 - Sep 24
47ft Viking Yacht · 2 Pools · Perry Marina · Key West
House | Exterior

8. 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 ￥29,312
￥47,553 total
includes taxes & fees
Sep 23 - Sep 24
Island View 1BR Residence With Balcony
Pool

9. Living the Dream Key West Style

Living the Dream Key West Style
Stock Island
10.0 out of 10, Exceptional, (62 reviews)
"Great would definitely stay again "
United States
Zach C.
The price is ￥50,202
￥62,596 total
includes taxes & fees
Oct 4 - Oct 5
Living the Dream Key West Style
Beach nearby

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 ￥39,220
￥63,949 total
includes taxes & fees
Sep 24 - Sep 25
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Beach nearby

11. Sunny Condo with WiFi, Hot Tub, Pool & Tennis

Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Key West
9.4 out of 10, Exceptional, (122 reviews)
"We loved the location."
United States
Aneesah D.
The price is ￥102,173
￥128,161 total
includes taxes & fees
Sep 24 - Sep 25
Sunny Condo with WiFi, Hot Tub, Pool & Tennis
Outdoor dining

12. 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.
The price is ￥26,192
￥46,672 total
includes taxes & fees
Sep 25 - Sep 26
Poolside Cottage #411
Beach nearby

13. Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family

Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
Key West
8.8 out of 10, Excellent, (218 reviews)
"The two bedroom apartment offered everything we needed, and the pool and hot tub were welcome additions. We liked that it was close to the airport."
United States
Ann A.
The price is ￥71,396
￥89,422 total
includes taxes & fees
Sep 23 - Sep 24
Watch Sunsets from Your Deck, Shared Pool/Hot Tub - Perfect for the Whole Family
2 bedrooms, iron/ironing board, WiFi, bed sheets

14. 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 Tortuga at Sunrise Suites - Balcony & Pool
Beach

15. Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking

Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking
Key West
8.8 out of 10, Excellent, (124 reviews)
"Great location!"
United States
Rodney W.
The price is ￥93,175
￥117,251 total
includes taxes & fees
Sep 26 - Sep 27
Cozy Dog-Friendly Condo w/ Shared Pool, Hot Tub, Private Deck & Parking
Outdoor dining

16. 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 ￥29,023
￥49,653 total
includes taxes & fees
Oct 18 - Oct 19
Poolside Cottage #412
Coffee/tea maker, fridge, microwave, oven

17. 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 ￥39,220
￥88,363 total
includes taxes & fees
Sep 23 - Sep 24
Grand Marina Suite - Poolside & Waterfront Condo
House | 2 bedrooms

18. Resort View 2BR Residence

Resort View 2BR Residence
2.0 star property
Key West
The price is ￥44,064
￥82,576 total
includes taxes & fees
Oct 5 - Oct 6
Resort View 2BR Residence
Pool

19. Paradise found

Paradise found
Stock Island
9.8 out of 10, Exceptional, (39 reviews)
"Great to stay. Good places to eat close by."
United States
Robert B.
The price is ￥51,755
￥102,645 total
includes taxes & fees
Sep 29 - Sep 30
Paradise found
Living area

20. The Grand Cayman | Beautifully Remodeled Key West!

The Grand Cayman | Beautifully Remodeled Key West!
Key West
9.6 out of 10, Exceptional, (19 reviews)
"Great facility and loved the location! "
United States
Matt R.
The price is ￥27,266
￥77,924 total
includes taxes & fees
Sep 24 - Sep 25
The Grand Cayman | Beautifully Remodeled Key West!
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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

8/10 Good
"Dont forget the addition 54.00 a night fee after you already pay 1600 something for 4 nights"
Janet 4-night trip
Posted 8 hours ago
Margaritaville Beach House Key West

Find out more about Cow Key

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Look no further and take a look at our great range of rental properties in Cow Key!

Frequently asked questions

Are there vacation rentals in Cow Key?

Yes, we have vacation rentals near well known local attractions in Cow Key, or you can select a more secluded option if you're looking for relaxation. 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 vacation rentals that Cow Key has to offer?

Sugarloaf Key RV Resort & Cottages: Visitors like this Cow Key vacation home rental. It 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 vacation 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 Florida Keys Eco - Discovery Center, or get out into nature at a spot like Florida Keys Beaches. In the larger area, you’ll find Duval Street and Robbie's.

What are vacation rentals like in Cow Key?

Vacation rentals are private accommodations you can stay in for several days or more in Cow Key. Vacation rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitized environment, a vacation rental can offer a sense of safety away from shared hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips.