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

Villas in Cow Key

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Cow Key villas

Exterior

1. Poolside Studio Villa Steps from Duval!

Poolside Studio Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (25 reviews)
"Great place to stay"
United States
Benjamin K.
$371 nightly
The price is $412
Oct 6 - Oct 7
Total with taxes and fees
Poolside Studio Villa Steps from Duval!
Exterior

2. Poolside King Room Steps from Duval!

Poolside King Room Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (1 review)
"If you’re looking to stay in Old Town this is the perfect location. Pool right outside the room, FREE Happy Hour from 4-5 and very accommodating hosts. Good for families or couples alike. Awesome!"
United States
Michael L R.
$376 nightly
The price is $417
Oct 7 - Oct 8
Total with taxes and fees
Poolside King Room Steps from Duval!
Exterior

3. Poolside Queen Room Steps from Duval!

Poolside Queen Room Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (3 reviews)
"Great location, great hosts, would definitely stay here again."
United States
Ryan C.
Poolside Queen Room Steps from Duval!
Exterior

4. Loft Villa Steps from Duval!

Loft Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (22 reviews)
"The complimentary breakfast and happy hour was great! The pool and hot tub were wonderful "
United States
Linda W.
$454 nightly
The price is $504
Oct 5 - Oct 6
Total with taxes and fees
Loft Villa Steps from Duval!
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5. Two Bedroom Two Bath Poolside Villa Steps from Duval!

Two Bedroom Two Bath Poolside Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (65 reviews)
"Cannot say enough good things about the Villas. They reached out to me weeks/days before and followed up during our stay. The happy hour and breakfast was an added bonus. Pool and rooms were awesome and location can’t be beat. Will stay there again!"
United States
Matt S.
$684 nightly
The price is $759
Sep 28 - Sep 29
Total with taxes and fees
Two Bedroom Two Bath Poolside Villa Steps from Duval!
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6. Two Bedroom Two Bath Balcony Villa Steps from Duval!

Two Bedroom Two Bath Balcony Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (47 reviews)
"Great place to stay and great owners!"
United States
Michael W.
$676 nightly
The price is $751
Sep 27 - Sep 28
Total with taxes and fees
Two Bedroom Two Bath Balcony Villa Steps from Duval!
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7. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
3.5 star property
Summerland Key
7.4 out of 10, Good, (3 reviews)
"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "
United States
Preetam
$925 nightly
The price is $1,041
Sep 9 - Sep 10
Total with taxes and fees
Atlantic View Luxury Villa with Pool
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

Beachside Resort & Residences

Beachside Resort & Residences

10/10 Excellent
"Very happy with this stay. The location is perfect with shopping food coffee The hotel area and the room were so clean the staff were very friendly and gave us everything we needed it was very quiet until the morning Loved hearing the chicken arlam and the shuttle are very services."
Chonthasorn 2-night trip
Posted less than an hour ago
Beachside Resort & Residences

Find out more about Cow Key

Cow Key Villas information

Number of reviews
166
Accommodation
30 Villas
Lowest Price
$412
Highest Price
$1,041

Frequently asked questions

How much do villas in Cow Key cost?
Villas in Cow Key cost between $412 and $1,041 per night. These getaways provide the privacy to enjoy your own space at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Cow Key?
A traveler favorite is Old Town Garden Villas. Base yourself at this 3.5-star property which comes with a garden and WiFi. 6 Bedroom Duval Compound - Old Town Key West is another highly rated option to look into. Spend your break at this 4-star stay and make the most of amenities including a barbecue grill and a jetted bathtub. You'll have your pick of multiple villas in Cow Key with a total average guest review rating of 9.6.
How many villas are there in Cow Key?
There are 30 villas in Cow Key. No matter if you're taking a trip with the little ones or planning a weekend escape with your besties, Expedia can help you find the best space for your squad.
Are there any family-friendly villas in Cow Key?
Traveling with the kids in Cow Key is easy at 6 Bedroom Duval Compound - Old Town Key West. With conveniences like a barbecue grill and laundry facilities, everyone can chill out and relax at this 4-star stay. Duval Penthouse is another family-friendly option perfect for spending your downtime with the ones you love most. It has a 4-star rating and amenities including a barbecue grill and laundry facilities. Cow Key has loads of family-friendly attractions to check out when you need to keep the kids busy. Smathers Beach and South Beach offer fun for both young and old.
Are there any 5-star villas in Cow Key?
Cow Key unfortunately doesn't have any 5-star villas — but you can still have a stylish stay here! Why not check in to 6 Bedroom Duval Compound - Old Town Key West? Located approximately 4 miles from the downtown area, this 4-star option offers conveniences like a jetted bathtub and a rooftop terrace. Duval Penthouse is another impressive choice just 4 miles from the center of Cow Key. Also rated 4 stars, it features a jetted bathtub and a swimming pool.
Why book your villa in Cow Key with Expedia?
We think arranging a vacation should be a breeze, so if you're looking for villas at the right price, Expedia is here to help. Save those pennies and pick an all-inclusive stay, or splurge on a 5-star villa to spoil your loved ones. Use our search filters to find a retreat in Cow Key that checks your boxes.
How can I find cheap villas in Cow Key?
Expedia is here to help you track down cheap villas in Cow Key. Use the filter tool to select star rating, budget and amenities to refine your search and find the best place to stay in a matter of clicks.

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