Villas in Cow Key

Compare 29 Villas in Cow Key with updated reviews, rates, and availability.

Pool
Two Bedroom Two Bath Poolside Villa Steps from Duval!
10.0 out of 10, Exceptional, (32)
"I would not consider staying anywhere other than Key West Villas when visiting Key West. Hosts Kevin and his wife were super attentive, friendly and couldn't have been more hospitable! Our villa was well equipped and clean. Really enjoyed the daily Happy Hour gathering which included a wide variety of drinks and of course, the shot of the day! Look forward to returning here for another vacation!"
The price is $449
$569 total
includes taxes & fees
May 22 - May 23
Two Bedroom Two Bath Poolside Villa Steps from Duval!
Pool
Luxury Oceanview Pool Eco-friendly Villa Near Key West
10.0 out of 10, Exceptional, (1)
"Stayed at the house for a week with a large group of friends for a bachelor party. The house had everything you need and everything works. There is a nice view and the pool out back is decently shaded by a sun cover. There were some non grocery items like trash bags, laundry stuff, tin foil, etc so we didn’t need to be exhaustive with our purchasing at the store. The basketball net in the ad was missing a hoop but that was the only small thing awry. The property is great and the owner has...
Luxury Oceanview Pool Eco-friendly Villa Near Key West
Pool
Two Bedroom Two Bath Balcony Villa Steps from Duval!
10.0 out of 10, Exceptional, (34)
"Great place to stay and great owners!"
The price is $549
$696 total
includes taxes & fees
May 29 - May 30
Two Bedroom Two Bath Balcony Villa Steps from Duval!
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Pool
Harborwalk Hideaways by Brightwild |Prime Location
10.0 out of 10, Exceptional, (3)
"This property worked out fantastic for us. We had a large group for a bachelorette. We occupied the whole compound utilizing all 3 villas. The court yard with small pool was so cute and we loved sitting there and chatting about our previous night as a group while sipping our morning coffee. The rooms were super cute, clean and fit us all comfortably (we had 12 girls). We needed to contact the property managers a couple of times and they answered quickly and serviced our requests in a very timely...
The price is $1,188
$2,052 total
includes taxes & fees
Jun 16 - Jun 17
Harborwalk Hideaways by Brightwild |Prime Location
Pool
Poolside Studio Villa Steps from Duval!
10.0 out of 10, Exceptional, (11)
"Will definitely stay here again! Awesome couple runs the place and everything from the parking to the happy hour fun to the very comfortable villa with a pool made this trip to Key West one of our best yet! A+ all the way!"
The price is $329
$417 total
includes taxes & fees
Jun 11 - Jun 12
Poolside Studio Villa Steps from Duval!
Property grounds
Emerald Seas - Florida Keys Ocean Front Paradise!
10.0 out of 10, Exceptional, (11)
"Beautiful, comfortable house on the open water with beautiful views. Did not want to leave."
The price is $425
$729 total
includes taxes & fees
May 22 - May 23
Emerald Seas - Florida Keys Ocean Front Paradise!
Pool
Loft Villa Steps from Duval!
10.0 out of 10, Exceptional, (7)
"The location was perfect and the owners were amazing. The breakfast and happy hour were wonderful, I was always receiving texts to check on us. Would definitely stay here again!"
The price is $349
$443 total
includes taxes & fees
May 22 - May 23
Loft Villa Steps from Duval!
Pool
Poolside Queen Room Steps from Duval!
10.0 out of 10, Exceptional, (1)
"Perfect location, awesome hosts, and the Key West Villas were wonderful. The pool area provided a tranquil area to relax."
The price is $249
$316 total
includes taxes & fees
May 28 - May 29
Poolside Queen Room Steps from Duval!
Pool
One Bedroom Deck Villa Steps from Duval!
10.0 out of 10, Exceptional, (6)
"Outstanding place to stay! Awesome amenities and great location! A definite stay and a place to return again! Nice continental breakfast, afternoon snacks, excellent happy hour and specialty shot of the day! Beautiful grounds, great pool, awesome hosts too! Thanks for a great stay at Key West Villas!"
The price is $329
$417 total
includes taxes & fees
May 22 - May 23
One Bedroom Deck Villa Steps from Duval!
Pool
Poolside King Room Steps from Duval!
10.0 out of 10, Exceptional, (1)
"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!"
The price is $279
$354 total
includes taxes & fees
May 29 - May 30
Poolside King Room Steps from Duval!
Pool
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
10.0 out of 10, Exceptional, (4)
"Our 2nd trip to Hyatt Beach Resort and love everything about it! Bathrooms were recently updated and place was clean, staff helpful and we'd go back again!"
Hyatt Beach House Resort. Key West. 2 Bedroom. 2 Bathroom WEEK Stay.
Pool | Outdoor pool
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
9.8 out of 10, Exceptional, (146)
"Great location if you want to be in the middle of Old Town, with lots to do within walking distance! Enjoyed this large condo, enough room for many. Also used the pool more than originally thought but it was very refreshing! Only downfall... the bar next door was very loud until 1a.m. almost every night, bring your ear plugs!!! Would definitely stay at this location again!"
Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Pool | Outdoor pool, a heated pool
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
9.8 out of 10, Exceptional, (70)
"This property is ideal for a large group with plenty of space to spread out and also to gather. Perfectly located within walking distance of everything. Both units are very well appointed, extremely clean, and very comfortable. This is our second time renting this property, and we hope to do it again! We were better acclimated this time and enjoyed our stay that much more. So convenient and easy, and the property manager is super friendly and responsive."
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
Beach nearby
Coral Garden by AvantStay | Great Location w/ Balcony & Shared Pool
9.6 out of 10, Exceptional, (4)
"We enjoyed 4 nights and had a wonderful trip. The home was very clean and colorful and stylish. It was quiet and we slept well. There was not a lot of room in the 2nd bedroom for the extra bed that was in the closet. With the extra bed set up you could not access the porch without climbing over the beds. We ended up bringing the extra bed downstairs and one of our kids slept on the main floor. The beds were all very comfortable. We enjoyed spending time on the porches. It was close enough to the...
Coral Garden by AvantStay | Great Location w/ Balcony & Shared Pool
Outdoor dining
Coral Palm by AvantStay | Key West Walkable
9.6 out of 10, Exceptional, (9)
"Property was very nice and clean in a gated community. After we arrived we went to fix supper and discovered the oven was NOT working. With it being around the holidays they were not able to get a repairman to get it fixed until after our stay. I would have appreciated some type of little refund as the reason we like VRBO’s is so we can eat one meal a day a home and not have to eat out all the time. 7 people eating out all the time gets expensive in a hurry. And we had already grabbed a few...
Coral Palm by AvantStay | Key West Walkable
Condo, 1 Bedroom, Private Pool (Old Town Garden Villas - Bermuda Suit) | Interior
Old Town Garden Villas
3.5 star property
9.6 out of 10, Exceptional, (8)
"Beautiful gardens, very relaxing, and a perfect location "
Old Town Garden Villas
Pool
Pilar's Cottage by Brightwild | Studio w/Pool!
9.4 out of 10, Exceptional, (9)
"Location could not be more ideal, walking to everything. Our host Jason was so accommodating and quick to respond to any needs we had."
The price is $215
$413 total
includes taxes & fees
May 29 - May 30
Pilar's Cottage by Brightwild | Studio w/Pool!
Property grounds
Coral Villa by AvantStay | Close 2 DT Key West
9.2 out of 10, Wonderful, (27)
"Great location and great access. Safe and secure."
Coral Villa by AvantStay | Close 2 DT Key West
Flat-screen TV, offices
African Queen by Brightwild | GREAT Suite
7.6 out of 10, Good, (5)
"Location of property offers convenient access to historic downtown whenever you want. However, the option to privately and quietly spend time in the outside area is there as well. Well maintained property,"
The price is $260
$467 total
includes taxes & fees
Jun 16 - Jun 17
African Queen by Brightwild | GREAT Suite
Pool
Key West Paradise w/ Private Pool + Ocean View
Key West Paradise w/ Private Pool + Ocean View
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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.

Other property types in Cow Key

Outdoor dining
Poolside Cottage #411
10.0 out of 10, Exceptional, (16)
"My son and his new wife stayed here for their honeymoon and they absolutely loved it!"
The price is $216
$369 total
includes taxes & fees
May 28 - May 29
Poolside Cottage #411
Pool
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
9.8 out of 10, Exceptional, (190)
"The house location was absolutely amazing. Everything was top notch. I would recommend this house over and over again, the back yard is so tranquil and the layouts of the room worked out well for bigger parties."
The price is $699
$1,520 total
includes taxes & fees
May 22 - May 23
Historic Mansion in Old Town Key West with Private Pool - Sleeps 16!
Beach towels
Steps from Duval, Pool & Bikes $129-$299 Night!
9.6 out of 10, Exceptional, (330)
"My husband and I just got back from Key West. We had a fabulous time and loved where we stayed. Ken, the owner, is terrific. Great communication, excellent tips on things to do and places to eat. It a large house and you have a room to stay in with your own bathroom, small kitchen and bed. It was perfect for us. We will definitely be back next time we visit Key West. Thanks Ken for being a great host!!!"
The price is $139
$291 total
includes taxes & fees
Jun 20 - Jun 21
Steps from Duval, Pool & Bikes $129-$299 Night!
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.

Cow Key Villas information

Number of reviews
346
Accommodation
29 Villas
Lowest Price
$215
Highest Price
$1,188

Frequently asked questions

How much do villas in Cow Key cost?
You can expect to pay between $215 and $1,188 per night for a villa in Cow Key. No matter your budget, an epic getaway is only a click away on Expedia. This price was 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?
Expedia guests love staying at Old Town Garden Villas. Kick back at this 3.5-star property which offers a garden and a nearby beach. 6 Bedroom Duval Compound - Old Town Key West is another sought-after option worth looking into. Book into this 4-star stay and you’ll have access to conveniences including a swimming pool and a barbecue grill. You’ll have your pick of multiple villas in Cow Key with a total average guest review rating of 9.7.
How many villas are there in Cow Key?
Cow Key has 29 villas to select from. Find a place that’s perfect quickly and easily by clicking the “Villa” checkbox under the “Property type” tab in our filter tool.
Are there any 5-star villas in Cow Key?
Although there aren’t any 5-star villas in Cow Key, there are some 4-star options that have just what you need. Located around 4 mi from downtown, Duval Penthouse comes with useful amenities like a rooftop terrace and a terrace. Another upscale stay is 6 Bedroom Duval Compound - Old Town Key West. It’s around 4 mi from central Cow Key and features conveniences such as a swimming pool and a jetted bathtub.
Why book your villa in Cow Key with Expedia?
With Expedia, you’ll have no trouble finding your ideal villa in Cow Key. Vacationing with the kids? Use our handy filters to look for stays with a kitchen or a pool. If you have a budget in mind, decide on how much you want to spend and the star rating of the property. We’ll help you find the perfect stay in tune with your style and taste.
How can I find cheap villas in Cow Key?
Expedia can help you easily source cheap villas in Cow Key. Simply use the filter tool to choose amenities, budget and star rating to refine your search and find an amazing place to stay in just a few clicks.
What is there to do near my villa in Cow Key?
There are lots of fabulous things to put on your itinerary in Cow Key. Explore attractions like Smathers Beach, South Beach and Fort Zachary Taylor Historic State Park. Higgs Beach, Key West Aquarium and Boca Chica Nude Beach are also on many to-do lists.

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