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

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Our top choices for Cow Key vacation homes

1. Poolside Cottage #411

Poolside Cottage #411
Key West
9.8 out of 10, Exceptional, (72 reviews)
"I loved having the pool right outside the door! It was extremely clean and perfectly located for our needs. I really enjoyed sitting outside in the evenings. I would absolutely stay here again and recommend it to others!"
United States
Cristy D.
Poolside Cottage #411

2. Poolside Cottage #412

Poolside Cottage #412
Key West
9.4 out of 10, Exceptional, (37 reviews)
"Wonderful stay. Thank you."
United States
shannon b.
The price is AED 680
AED 1,111 total
includes taxes & fees
29 Nov - 30 Nov
Poolside Cottage #412

3. Casa Havana | Old Town Condo w/ Pool & Balcony

Casa Havana | Old Town Condo w/ Pool & Balcony
Old Town Key West
9.2 out of 10, Wonderful, (12 reviews)
"Wonderful location, clean, quiet. All around it was a great experience staying here!"
United States
Kim T.
The price is AED 786
AED 2,758 total
includes taxes & fees
22 Nov - 23 Nov
Casa Havana | Old Town Condo w/ Pool & Balcony

4. Slice of Paradise

Slice of Paradise
Stock Island
10.0 out of 10, Exceptional, (5 reviews)
"House was clean, what we expected, host responded promptly and accurately, pool was great."
United States
Cathy S.
Slice of Paradise

5. Sea Esta Suite | Located On Iconic Duval w/ Pool

Sea Esta Suite | Located On Iconic Duval w/ Pool
Old Town Key West
9.8 out of 10, Exceptional, (58 reviews)
"Located on Duval Street made all points of interest in old town an easy walk."
United States
Rick H.
The price is AED 710
AED 2,649 total
includes taxes & fees
12 Nov - 13 Nov
Sea Esta Suite | Located On Iconic Duval w/ Pool

6. Road's End | Prime Old Town Location! Updated Home w/ Pool

Road's End | Prime Old Town Location! Updated Home w/ Pool
Old Town Key West
9.6 out of 10, Exceptional, (28 reviews)
"Charming, clean accommodations in a conveniently located area of Key West for walking to sites and renting bicycles"
United States
BARBARA Y.
The price is AED 541
AED 1,543 total
includes taxes & fees
15 Nov - 16 Nov
Road's End | Prime Old Town Location! Updated Home w/ Pool

7. 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, (139 reviews)
"We had an awesome stay! We enjoyed being able to use the bikes and have covered parking, too. We would definitely stay here again!"
United States
Melanie K.
The price is AED 1,041
AED 2,145 total
includes taxes & fees
9 Nov - 10 Nov
Luxury Condo-FREE PARKING,WIFI,BIKES,BIG POOL,WALK TO RESTAURANTS, BEACH CHAIRS

8. Shared Pool & Near Duval - Curry House Room 9

Shared Pool & Near Duval - Curry House Room 9
Old Town Key West
7.4 out of 10, Good, (20 reviews)
"Nice and clean.Quiet and convenient to Duval.We will be back!"
United States
Deborah L.
The price is AED 375
AED 1,153 total
includes taxes & fees
18 Nov - 19 Nov
Shared Pool & Near Duval - Curry House Room 9

9. Capmar House at Lunara Bay

Capmar House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (29 reviews)
"The Best VRBO I have stayed in "
United States
Wilbert C.
The price is AED 2,200
AED 5,222 total
includes taxes & fees
10 Nov - 11 Nov
Capmar House at Lunara Bay

10. Waterlane House at Lunara Bay

Waterlane House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (38 reviews)
"Everything was great"
United States
Justin S.
The price is AED 2,200
AED 5,097 total
includes taxes & fees
8 Nov - 9 Nov
Waterlane House at Lunara Bay

11. The Seagate Estate at Lunara Bay

The Seagate Estate at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (30 reviews)
"Great property, terrific hosts - amazing location!"
United States
Jason T.
The price is AED 2,935
AED 6,133 total
includes taxes & fees
16 Nov - 17 Nov
The Seagate Estate at Lunara Bay

12. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
2.0 star property
Raccoon Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful property, 4 large bedroom and en suite bathroom, private pool we really liked our stay"
France
Karen
The price is AED 2,822
AED 5,720 total
includes taxes & fees
10 Nov - 11 Nov
Capmar House by Brightwild Huge Home Pool

13. Mastway House at Lunara Bay - Wellness Home

Mastway House at Lunara Bay - Wellness Home
Raccoon Key
9.6 out of 10, Exceptional, (36 reviews)
"My family and I had a very nice stay."
United States
Robert L.
The price is AED 2,200
AED 5,222 total
includes taxes & fees
10 Nov - 11 Nov
Mastway House at Lunara Bay - Wellness Home

14. The Shellstone House at Solaire Lunara Bay

The Shellstone House at Solaire Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (7 reviews)
"Great property / location. Perfect house with wonderful amenities!!!"
United States
Dudley S.
The price is AED 3,669
AED 8,176 total
includes taxes & fees
10 Nov - 11 Nov
The Shellstone House at Solaire Lunara Bay

15. Spacious 3-bedroom townhome on Stock Island with resort style pool.

Spacious 3-bedroom townhome on Stock Island with resort style pool.
Stock Island
10.0 out of 10, Exceptional, (8 reviews)
"Perfect for our family trip to Key West. Great location and we enjoyed the pool and nearby restaurants. Easy check in and check out process and clear, timely communication with the owner. "
United States
Samantha P.
The price is AED 1,102
AED 2,314 total
includes taxes & fees
23 Nov - 24 Nov
Spacious 3-bedroom townhome on Stock Island with resort style pool.

16. Suncoast House at Lunara Bay

Suncoast House at Lunara Bay
Raccoon Key
9.6 out of 10, Exceptional, (44 reviews)
"Beautiful House, super clean, perfect location "
United States
carlos s.
The price is AED 2,200
AED 5,695 total
includes taxes & fees
9 Nov - 10 Nov
Suncoast House at Lunara Bay

17. Aquaria House at Lunara Bay

Aquaria House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (46 reviews)
"Loved the property and the location!! It was perfect for me and the family. Short commute to everything we needed and wanted. I can't wait to go back for the next visit!!"
United States
Chris H.
The price is AED 2,200
AED 5,097 total
includes taxes & fees
8 Nov - 9 Nov
Aquaria House at Lunara Bay

18. Spindrift House at Lunara Bay

Spindrift House at Lunara Bay
Raccoon Key
10.0 out of 10, Exceptional, (35 reviews)
"Property was good would stay here again!"
United States
Richard K.
The price is AED 2,200
AED 5,097 total
includes taxes & fees
8 Nov - 9 Nov
Spindrift House at Lunara Bay

19. Evershore Estate at Lunara Bay | Wellness Home

Evershore Estate at Lunara Bay | Wellness Home
Raccoon Key
9.8 out of 10, Exceptional, (30 reviews)
"The house is perfect for our family. Access to water, pool and close enough to key west!"
United States
John F.
The price is AED 2,200
AED 5,222 total
includes taxes & fees
24 Nov - 25 Nov
Evershore Estate at Lunara Bay | Wellness Home

20. Altair House at Lunara Bay

Altair House at Lunara Bay
Raccoon Key
9.8 out of 10, Exceptional, (15 reviews)
"host was very kind to let us do early check-in and late check out. The house is great, was very clean, everything was working perfectly."
United States
Esteban M.
The price is AED 2,935
AED 6,871 total
includes taxes & fees
9 Nov - 10 Nov
Altair 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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