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

Search Cow Key Villa Rentals from CA $508

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Cow Key villas

A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

1. 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.
The price is CA $402
CA $508 total
includes taxes & fees
Sep 3 - Sep 4
Poolside Queen Room Steps from Duval!
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

2. 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.
The price is CA $456
CA $572 total
includes taxes & fees
Sep 4 - Sep 5
Poolside Studio Villa Steps from Duval!
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

3. 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.
The price is CA $456
CA $572 total
includes taxes & fees
Sep 4 - Sep 5
Poolside King Room Steps from Duval!
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

4. One Bedroom Deck Villa Steps from Duval!

One Bedroom Deck Villa Steps from Duval!
Old Town Key West
10.0 out of 10, Exceptional, (10 reviews)
"This place was great one of the best host I’ve ever had!!"
United States
Donnie S.
The price is CA $553
CA $694 total
includes taxes & fees
Sep 4 - Sep 5
One Bedroom Deck Villa Steps from Duval!
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

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, (63 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.
The price is CA $833
CA $1,034 total
includes taxes & fees
Sep 28 - Sep 29
Two Bedroom Two Bath Poolside Villa Steps from Duval!
A property named Villas Key West with a covered entrance, a white picket fence, and lush greenery.

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.
The price is CA $833
CA $1,034 total
includes taxes & fees
Sep 27 - Sep 28
Two Bedroom Two Bath Balcony Villa Steps from Duval!
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

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
The price is CA $717
CA $1,352 total
includes taxes & fees
Sep 18 - Sep 19
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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Clean, great staff. Very nice and highly recommend"
Sofia 2-night trip
Posted less than an hour ago
Southernmost Beach Resort and Guesthouses

Find out more about Cow Key

Cow Key Villas information

Number of reviews
152
Accommodation
30 Villas
Lowest Price
CA $508
Highest Price
CA $1,352

Frequently asked questions

How much do villas in Cow Key cost?
Villas in Cow Key cost between CA $508 and CA $1,352 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 traveller favourite 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?
Travelling 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 6 kilometres 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 6 kilometres from the centre 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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