Beginning of main content
Cow Key Vacation Rentals
Save an average of 15% on thousands of properties with Expedia Rewards
Most properties are fully refundable. Because flexibility matters.
Search over 2.9 million properties and 550 airlines worldwide.
Check Cow Key vacation rental availability
Vacation Rentals in Cow Key
1445 S Roosevelt Blvd, Key West, FL, 33040
Stay at this 3-star condo in Key West. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the spacious rooms in our reviews. ...
8.2/10 Very Good! (728 reviews)
"Great place"
Reviewed on Mar 20, 2023
5130 Overseas Hwy, Key West, FL, 33040
The price is $188 per night from Apr 16 to Apr 17
$188
per night
Apr 16 - Apr 17
Stay at this houseboat in Key West. Enjoy free WiFi, free parking, and a marina. Popular attractions Duval Street and Key West Tropical Forest and Botanical ...
8.6/10 Excellent! (4 reviews)
"Cool place."
Reviewed on Feb 25, 2023
Key West, FL
The price is $198 per night from Mar 25 to Mar 26
$198
per night
Mar 25 - Mar 26
Stay at this houseboat in Key West. Enjoy 2 bedrooms. Popular attractions Duval Street and Smathers Beach are located nearby. Discover genuine guest reviews ...
5.6/10 (6 reviews)
Boat is not at a dock.
"I don’t feel like the ad accurately communicated the amount of time necessary to go from Duval Street to the boat. It took anywhere between two hours and six hours. To go from the Devaul Street to the boat and consumed more time than I would’ve liked. I did have a good time. I just feel like it was ..."
Reviewed on Jan 19, 2023
Save an average of 15% on thousands of hotels when you're signed in
Key West, FL
The price is $198 per night from Mar 26 to Mar 27
$198
per night
Mar 26 - Mar 27
Stay at this houseboat in Key West. Enjoy WiFi, barbecue grills, and an onsite playground. Popular attractions Duval Street and Key West Golf Club are located ...
8.6/10 Excellent! (4 reviews)
"Had to wit to be taken from the house boat to land"
Reviewed on Mar 3, 2023
Key West, FL
The price is $245 per night from Apr 10 to Apr 11
$245
per night
Apr 10 - Apr 11
Stay at this houseboat in Key West. Enjoy a kitchen, 2 bedrooms, and an in-room coffeemaker. Popular attractions Duval Street and Schooner Western Union are ...
6.8/10 (5 reviews)
Amazing location, better than any hotel
"Could have been more comfortable and more lighting. There is no dinghy so don’t expect one, Ethan was great at picking up except for the first night when we had to get someone else to take us. Overall loved the experience and Art was great at communicating. Beats staying hotel for location and sunrise ..."
Reviewed on Mar 16, 2023
Key West, Florida
The price is $234 per night from Apr 13 to Apr 14
$234
per night
Apr 13 - Apr 14
Stay at this apartment in Key West. Enjoy free WiFi, a garden, and a patio. Popular attractions Duval Street and MLK Community Pool & Community Center are located ...
9.4/10 Exceptional! (14 reviews)
Carey's Corner
"Careys Corner was nice and cozy. Property was clean and location was pretty convenient to all areas we wanted to see. Neighborhood left a little to be desired."
Reviewed on Mar 18, 2023
Key West, FL
The price is $270 per night from Mar 25 to Mar 26
$270
per night
Mar 25 - Mar 26
Stay at this houseboat in Key West. Enjoy 2 bedrooms. Popular attractions Duval Street and Smathers Beach are located nearby. Discover genuine guest reviews ...
2/10 (4 reviews)
Floating junk
"Nothing good to say. Waited over 4 hours for water taxi."
Reviewed on Mar 9, 2023
Key West, FL
The price is $209 per night from Apr 2 to Apr 3
$209
per night
Apr 2 - Apr 3
Stay at this apartment in Key West. Enjoy a water park, WiFi, and a patio. Our guests praise the quiet rooms and the family amenities in our reviews. Popular ...
8.8/10 Excellent! (223 reviews)
Escape the cold in the northern plains
"We've been to KW several times and have stayed at this location a few times. Nice place, affordable, close to all the sites. Downfall is the room is very tiny, but we make it work. Pool onsite is a plus!"
Reviewed on Mar 11, 2023
Key West, Florida
The price is $301 per night from Mar 28 to Mar 29
$301
per night
Mar 28 - Mar 29
Stay at this condo in Key West. Enjoy free WiFi, onsite parking, and concierge services. Popular attractions Duval Street and Key West Firehouse Museum are located ...
9.4/10 Exceptional! (36 reviews)
Charming Little Nest
"This was a charming little nest to stay in, especially for a first time visit to Key West. A very historic building in the Old Town district. We loved that you provided coffee and tea, ice, water, fresh fruit and an abundance of clean towels. The pool was lovely. Thank you."
Reviewed on Feb 16, 2023
Key West, FL
The price is $229 per night from Apr 21 to Apr 22
$229
per night
Apr 21 - Apr 22
Stay at this apartment in Key West. Enjoy free WiFi, onsite parking, and an in-room DVD player. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (245 reviews)
Fun two days
"Unit had everything we needed. Close to Duval St and all the action. Most sights of interest were within walking distance. Visited beach at Ft Zachery Taylor nearby. Small pool in back was nice to come back to from the beach. Although shared with other units there was nobody there while using the ..."
Reviewed on Mar 21, 2023
Cudjoe Key, FL
Stay at this family-friendly vacation home in Cudjoe Key. Enjoy free WiFi, onsite parking, and an in-room DVD player. Our guests praise the pool and the helpful ...
9.2/10 Wonderful! (75 reviews)
The perfect birthday getaway!
"My favorite vacation yet.. Kristine’s place was clean & very comfortable. It’s only 25 minutes down the coastline to Key West. We traveled all the way up to Bahia Honda for the beautiful beaches, to Key Largo, for our dinner. We spent the the rest of the week in Key West! Dante’s is a must! We had ..."
Reviewed on Oct 3, 2022
Key West, FL
Stay at this vacation home in Key West. Enjoy WiFi, onsite parking, and tennis courts. Popular attractions Duval Street and Key West Firehouse Museum are located ...
9.6/10 Exceptional! (124 reviews)
"This was mine & my husbands first trip to Key West to celebrate our 1 year anniversary. This was a perfect place for the two of us. It’s located in the heart of all you want from Key west- shops, restaurants, grocery, sceneries, bars, art galleries, excursions, museums etc. Yet, the neighborhood ..."
Reviewed on Mar 11, 2023
Key West, FL
The price is $152 per night from Apr 5 to Apr 6
$152
per night
Apr 5 - Apr 6
Stay at this apartment in Key West. Enjoy a TV, cable/satellite TV, and an in-room coffeemaker. Popular attractions Duval Street and Tennessee Williams Key West ...
9.4/10 Exceptional! (9 reviews)
Perfect place for 1-2 people
"This was a perfect studio for me to stay at this week. I was a bridesmaid in a wedding at the Ernest Hemingway house, and this property backs up to the back side of the Hemingway house. It’s literally steps away from Duval st., tons of shops and restaurants, and a 7-10 minute walk from the beach. ..."
Reviewed on Oct 24, 2022
Key West, FL
Stay at this cottage in Key West. Enjoy free WiFi, barbecue grills, and a patio. Popular attractions Duval Street and Saint Mary Star of the Sea are located ...
10/10 Exceptional! (1 review)
Perfect Accommodations!
"Perfect location, lovely place. I got COVID so had to leave two days after arrival. Bummer!"
Reviewed on Dec 29, 2022
Key West, Florida
The price is $274 per night from Mar 29 to Mar 30
$274
per night
Mar 29 - Mar 30
Stay at this condo in Key West. Enjoy free WiFi, onsite parking, and concierge services. Popular attractions Duval Street and Key West Firehouse Museum are located ...
9.4/10 Exceptional! (26 reviews)
Love this property
"I loved this property. So quaint, quiet and peaceful. Even though it’s on Truman, it’s uniquely quiet. The pool is perfect and it was so clean. Easy check in and check out! I’ll be back!"
Reviewed on Mar 20, 2023
Key West, FL
The price is $204 per night from Apr 10 to Apr 11
$204
per night
Apr 10 - Apr 11
Stay at this condo in Key West. Enjoy onsite parking, tennis courts, and a balcony. Our guests praise the pool and the helpful staff in our reviews. Popular ...
8.6/10 Excellent! (21 reviews)
Would stay there again
"Parking was fine we had a spot. We always had one close to our area. We liked having the tennis court there we played tennis and saw other people playing pickle ball Overall, we would stay there again"
Reviewed on Feb 21, 2023
Key West, FL
The price is $129 per night from Mar 28 to Mar 29
$129
per night
Mar 28 - Mar 29
Stay at this condo in Key West. Enjoy a balcony, a TV, and cable/satellite TV. Our guests praise the quiet rooms in our reviews. Popular attractions Duval Street ...
9.4/10 Exceptional! (52 reviews)
Location!
"Located within walking distance of all the main attractions of Key West. Three blocks from the hop on-hop off trolley, Margaritaville on Duvall is about a 10 minute walk….five minute walk to Sunset Pier for “sundowners”, live music and great drinks! Parking was not as bad as the listing says it is, ..."
Reviewed on Feb 23, 2023
Key West, FL
The price is $188 per night from Apr 2 to Apr 3
$188
per night
Apr 2 - Apr 3
Stay at this apartment in Key West. Enjoy barbecue grills, a patio, and a TV. Our guests praise the comfy beds in our reviews. Popular attractions Duval Street ...
8.6/10 Excellent! (11 reviews)
Comfortable
"Secluded comfortable cottage"
Reviewed on Mar 12, 2023
Stock Island, FL
Stay at this apartment in Key West. Enjoy private pools, WiFi, and onsite parking. Our guests praise the helpful staff in our reviews. Popular attractions Duval ...
9.8/10 Exceptional! (40 reviews)
Location
"The location of this stay is perfect, right down to its private parking!"
Reviewed on Mar 12, 2023
245 Front Street, Key West, FL, 33040
Stay at this 3.5-star beach aparthotel in Key West. Enjoy a private beach, 3 bars/lounges, and breakfast. Our guests praise the pool and the helpful staff in ...
9/10 Wonderful! (57 reviews)
"Lovely place will come back next year! Everything and everyone excelente"
Reviewed on Jul 10, 2021
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 types of properties in Cow Key you may be interested in
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL, 33040
Fully refundableReserve now, pay when you stay
Southernmost Beach Resort
1319 Duval Street, Key West, FL, 33040
Fully refundableReserve now, pay when you stay
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.
Choosing the perfect Cow Key rental
If you're tired of staying in hotels, try a vacation rental for more privacy and space.
Dining in Cow Key
Cow Key is recognized for its restaurants. If you'd rather eat in, that's simple too, since most vacation rentals come with full-size kitchens.
Sightseeing around Cow Key
Some top sights around Cow Key include Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens, and Key West Art and Historical Society. If you're bringing the kiddos along, save a few hours for Nancy Forrester's Secret Garden, A Key Encounter, and Key West Aquarium. You can easily spend a leisurely day (or days) in the sunshine at Smathers Beach, Higgs Beach, or Simonton Street Beach. If you're planning to shop while in town, consider a trip to Mallory Dock. Explore the city's interesting landmarks including Mallory Square and Southernmost Point.
Packing for your Cow Key trip
If you're wondering what the weather will be like on your trip, check out the following seasonal average temperatures.
- January–March: 71°F
- April–June: 80°F
- July–September: 84°F
- October–December: 76°F
Booking your rental on Expedia
On Expedia, it's both safe and easy to book vacation rentals in Cow Key. We can help you contact the property owner directly to make any special arrangements. With all of the amenities available in your short-term rental, you're sure to have a memorable trip.
Frequently asked questions
Recent reviews of Cow Key propertiesExpedia verified reviews
Southernmost Beach Resort
Southernmost Beach Resort5/5 Excellent"Amazing place. My girlfriend and I had the best first trip together here. Super convenient to duval street. Right on the ocean and great pools."A verified traveler stayed at Southernmost Beach ResortPosted 1 day ago
Trending destinations on Expedia.com
- Destin Vacation Rentals
- Panama City Vacation Rentals
- Hilton Head Vacation Rentals
- Gulf Shores Vacation Rentals
- Key West Vacation Rentals
- Gatlinburg Vacation Rentals
- Maui Vacation Rentals
- Orlando Vacation Rentals
- Myrtle Beach Vacation Rentals
- Orange Beach Vacation Rentals
- Pigeon Forge Vacation Rentals
- Ocean City Vacation Rentals
- Outer Banks Vacation Rentals
- San Diego Vacation Rentals
- Siesta Key Vacation Rentals
- Galveston Vacation Rentals
- Clearwater Beach Vacation Rentals
- Palm Springs Vacation Rentals
- Florida Keys Vacation Rentals
- Lake Tahoe Vacation Rentals
- Lake of the Ozarks Vacation Rentals
- Florida Vacation Rentals
- Hawaii Vacation Rentals
- Michigan Vacation Rentals
Additional information about Expedia Group
8e04ca74-e7e0-482c-b1f5-d19bdef7a4024e827333-2e90-46ca-9a6d-7ecf1b1dbca6