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

Search and Rent Cow Key Condos

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

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

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Cow Key condo rentals

A wooden boardwalk leading to a hotel with a green roof, surrounded by lush greenery and palm trees.

1. The Butterfly Nest | Newly Updated w/ Shared Pool

The Butterfly Nest | Newly Updated w/ Shared Pool
Key West
9.8 out of 10, Exceptional, (48 reviews)
"Had a great time place is lovely "
United States
Sarah P.
$423 nightly
The price is $473
Sep 28 - Sep 29
Total with taxes and fees
The Butterfly Nest | Newly Updated w/ Shared Pool
A wooden boardwalk leading to a hotel with a green roof, surrounded by palm trees and a water feature.

2. The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!

The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
Key West
10.0 out of 10, Exceptional, (35 reviews)
"Very nice clean place. Had a minor problem with the beds after checking in but property manager was quick to respond and correct issue. Would stay here again. "
United States
Teri K.
$422 nightly
The price is $472
Sep 29 - Sep 30
Total with taxes and fees
The Samana Cay | Tropical, Airy Retreat w/ Private Balcony, Pool!
A swimming pool with lounge chairs, palm trees, and a view of the sunset over the water.

3. Pool View Suite | Beachside Resort

Pool View Suite | Beachside Resort
Key West
8.0 out of 10, Very good, (3 reviews)
"It was a holiday weekend. Key West in general all lodging was expensive. The room was very comfortable and clean. More than enough room. I was on the water which was amazing. The pool area was very awesome. Love that they have a bar and restaurant available. All the available excursions. I took advantage of the Sunset Tour. Property manager was available for any questions. Beachside staff was also very helpful. Would definitely visit again. Great Experience!! Thank you."
United States
Christie Y.
$229 nightly
The price is $255
Sep 28 - Sep 29
Total with taxes and fees
Pool View Suite | Beachside Resort
A hotel room with a bed, a television on a dresser, a chair, and a window with curtains.

4. The Tortuga at Sunrise Suites - Balcony & Pool

The Tortuga at Sunrise Suites - Balcony & Pool
Key West
8.6 out of 10, Excellent, (30 reviews)
"We were very impressed with the grounds. Loved the pool area. Was extremely clean"
United States
Margaret G.
$421 nightly
The price is $470
Oct 4 - Oct 5
Total with taxes and fees
The Tortuga at Sunrise Suites - Balcony & Pool
An outdoor tennis court with a blue surface, surrounded by a fence, palm trees, and buildings in the background.

5. The Grenada at Sunrise Suites - Shared Pool

The Grenada at Sunrise Suites - Shared Pool
Naval Air Station Key West
8.8 out of 10, Excellent, (13 reviews)
"We had a lovely time- thank you"
United States
Jackie Y.
$441 nightly
The price is $493
Sep 30 - Oct 1
Total with taxes and fees
The Grenada at Sunrise Suites - Shared Pool
A swimming pool area with multiple pools, palm trees, lounge chairs, and a clear blue sky.

6. Atlantic Parrot | Oceanfront Condo w/ Pool

Atlantic Parrot | Oceanfront Condo w/ Pool
Beachside
9.8 out of 10, Exceptional, (9 reviews)
"Absolutely beautiful property as well as room I loved it everything about it was beautiful "
United States
Misty C.
$630 nightly
The price is $704
Oct 6 - Oct 7
Total with taxes and fees
Atlantic Parrot | Oceanfront Condo w/ Pool
A wide sandy beach with palm trees and a clear sky.

7. Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.

Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
Key West
9.2 out of 10, Wonderful, (115 reviews)
"I enjoyed my stay at the resort, highly recommend!"
United States
Michelaine a.
$346 nightly
The price is $387
Sep 28 - Sep 29
Total with taxes and fees
Key West Condo close to the Ocean. 1 mile to Smathers & 3 miles to Duval St.
A bedroom with a bed, a chair, a wardrobe, and a bathroom visible through an open door.

8. The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!

The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!
Key West
$425 nightly
The price is $475
Sep 29 - Sep 30
Total with taxes and fees
The Tahiti Suite | Updated Key West Condo w/ Pool, Hot Tub, & Balcony!
A beach with lounge chairs, palm trees, and a water body.

9. Grand Marina Suite - Poolside & Waterfront Condo

Grand Marina Suite - Poolside & Waterfront Condo
Stock Island
9.6 out of 10, Exceptional, (33 reviews)
"Pool was great! Just far enough from Duval street to get away and relax if needed or jump in the car and head down for live music! "
United States
Brent H.
$479 nightly
The price is $535
Sep 28 - Sep 29
Total with taxes and fees
Grand Marina Suite - Poolside & Waterfront Condo
A wide sandy beach with palm trees and a clear sky.

10. Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony

Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
Key West
9.0 out of 10, Wonderful, (48 reviews)
"Great place for our 1 night in key west "
United States
Thadd W.
$346 nightly
The price is $387
Sep 28 - Sep 29
Total with taxes and fees
Two-bedroom, two-bath condo close to the Ocean. Full kitchen, living r & balcony
A wooden pathway leading to a beach with palm trees and a clear blue sky.

11. Island Time | Luxury Beach Condo w/ Pool & Hot Tub

Island Time | Luxury Beach Condo w/ Pool & Hot Tub
Key West
10.0 out of 10, Exceptional, (9 reviews)
"Neat and clean, spacious, easy walking access to the beach, nice amenities on the property with pool and hot tub."
United States
Stacey P.
$482 nightly
The price is $539
Sep 28 - Sep 29
Total with taxes and fees
Island Time | Luxury Beach Condo w/ Pool & Hot Tub
A tropical garden pathway leading to a building with a yellow facade and green shutters.

12. ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!

ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
Old Town Key West
9.6 out of 10, Exceptional, (112 reviews)
"Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The studio and surroundings matched photos posted and provided a Key West atmosphere and experience. Walking to Key West activities and sites was feasible. Very happy with and positive addition to our Key West visit."
United States
Ken L.
$258 nightly
The price is $288
Sep 28 - Sep 29
Total with taxes and fees
ROYAL PALM STUDIO ~ Adult Only, Studio w/ Community Pool & Close to Town!
A covered balcony with wicker chairs, a view of palm trees, and multiple flags.

13. NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!

NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
Old Town Key West
10.0 out of 10, Exceptional, (14 reviews)
"Wonderful stay, location was great!"
United States
Taffy M.
$246 nightly
The price is $274
Sep 28 - Sep 29
Total with taxes and fees
NIGHTCAP ~ On Duval St, Adult Only, Adjoining Rum Bar & Near Beaches!
A modern living room with a teal sofa, white coffee table, and dining area with white chairs.

14. Waterfront Dock Pool Condo Near Duval St Pet OK

Waterfront Dock Pool Condo Near Duval St Pet OK
Meadows
9.4 out of 10, Exceptional, (48 reviews)
"Hosts are super responsive and helpful. Perfect location. Would absolutely stay here again! "
United States
Amber G.
$349 nightly
The price is $390
Sep 30 - Oct 1
Total with taxes and fees
Waterfront Dock Pool Condo Near Duval St Pet OK
A tropical garden pathway leading to a building with a yellow facade and green shutters.

15. SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!

SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
Old Town Key West
9.8 out of 10, Exceptional, (137 reviews)
"Great place to stay"
United States
walter l.
$268 nightly
The price is $299
Sep 29 - Sep 30
Total with taxes and fees
SUGAR PALM STUDIO ~ Adult Only Studio w/ Community Pool & Close to Town!
A modern living room with a sofa, coffee table, and a dining area with a table and chairs. There is a kitchen area with cabinets and appliances.

16. The Grand Cayman | Beautifully Remodeled Key West!

The Grand Cayman | Beautifully Remodeled Key West!
Key West
9.6 out of 10, Exceptional, (19 reviews)
"Great facility and loved the location! "
United States
Matt R.
$422 nightly
The price is $472
Sep 29 - Sep 30
Total with taxes and fees
The Grand Cayman | Beautifully Remodeled Key West!
A wooden boardwalk leading to a hotel with a green roof, surrounded by lush greenery and palm trees.

17. The Andros | Incredible Views w/ Shared Pool

The Andros | Incredible Views w/ Shared Pool
Key West
9.0 out of 10, Wonderful, (45 reviews)
"Stayed 3,nights- would have stayed forever! Rick and staff could not have been more accommodating and friendly- the property was immaculate and maybe the most comfortable bed I’ve ever slept in! Rick was so knowledgeable about the island - had the answers for everything- such a lovely, relaxing stay, we will definitely be back!"
United States
Cynthia R.
$423 nightly
The price is $473
Sep 28 - Sep 29
Total with taxes and fees
The Andros | Incredible Views w/ Shared Pool
A modern living room with a sofa, coffee table, and a balcony with blue curtains.

18. The Cayo Coco | Key West Condo with Pool, Hot Tub!

The Cayo Coco | Key West Condo with Pool, Hot Tub!
Key West
9.6 out of 10, Exceptional, (15 reviews)
"Super clean place, location was perfect and quiet "
United States
Carlos R.
$423 nightly
The price is $473
Sep 28 - Sep 29
Total with taxes and fees
The Cayo Coco | Key West Condo with Pool, Hot Tub!
A modern living room with a sofa, coffee table, and a painting of a beach scene.

19. The Saint Kitts Suite | Breathtaking View, Heated Pool

The Saint Kitts Suite | Breathtaking View, Heated Pool
Key West
9.8 out of 10, Exceptional, (8 reviews)
"Beautifully decorated and great location. The condo was clean, comfortable, quiet and well stocked. Would recommend and definitely stay there again!"
United States
Linda W.
$422 nightly
The price is $472
Sep 29 - Sep 30
Total with taxes and fees
The Saint Kitts Suite | Breathtaking View, Heated Pool
A wooden boardwalk leading to a hotel with a green roof, surrounded by lush greenery and palm trees.

20. The Salt Cay | Updated! Stunning Sunset View, Pool

The Salt Cay | Updated! Stunning Sunset View, Pool
Key West
9.6 out of 10, Exceptional, (59 reviews)
"Everything was amazing! My family and I enjoyed every part of our stay; 10 out of 10 would recommend :)"
United States
Rebecca H.
$423 nightly
The price is $473
Sep 28 - Sep 29
Total with taxes and fees
The Salt Cay | Updated! Stunning Sunset View, 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Cow Key Hotel Reviews

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

8/10 Good
"Nice place, but over priced"
Lisa Michelle 6-night trip
Posted 7 hours ago
Southernmost Beach Resort and Guesthouses

Find out more about Cow Key

Cow Key Condo Rentals information

Number of reviews
425
Accommodation
544 Condo Rentals
Lowest Price
$255
Highest Price
$704

Frequently asked questions

How much do condos in Cow Key cost?
Expect to pay from $255 to $704 per night for condos in Cow Key. Whatever your budget, you'll find the perfect stay on Expedia. 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 condos in Cow Key?
A traveler favorite is Licence #cnd5403292 Apt A - 403. Make yourself at home at this 4-star property which features a nearby waterfront and an ocean view. Coconut Mallory Resort And Marina By Kees Vacations is another highly rated condo worth looking into. Book into this popular 3-star option and take advantage of amenities including a swimming pool and a barbecue grill. You can pick from multiple condos in Cow Key with a total average guest review rating of 9.5.
How many condos are there in Cow Key?
Take your pick of 544 condos in Cow Key. No matter if you're taking a trip with the family or organizing a weekend escape with your pals, Expedia will help you find the right space for your entire crew.
Are there any family-friendly condos in Cow Key?
Get comfortable at Licence #cnd5403292 Apt A - 403, a 4-star option just a quick drive from downtown. Conveniences here include a water view and a king-sized bed. Another family-friendly condo is Coconut Mallory Resort And Marina By Kees Vacations. A swimming pool and a barbecue grill help make this 3-star escape a guest favorite. After checking in and chilling out in your new digs, it's time to head out and explore some of the local sights. Smathers Beach and South Beach are among the family-friendly attractions in Cow Key.
Are there any 5-star condos in Cow Key?
You won't find any 5-star condos in Cow Key. But you will find some terrific 4-star stays. Check in to Licence #cnd5403292 Apt A - 403, about 2 miles from downtown. A beach view and a swimming pool are just two of the many amenities offered here. Seafarer's Refuge 4 Bedroom Home is another stylish option. It features a swimming pool and a tennis court and is located about 3 miles from the center of Cow Key.
Why book your condo in Cow Key with Expedia?
With Expedia, it's a cinch to find your ideal condo in Cow Key. Looking for someplace luxurious? Make the most of our filters to search for properties that are 5-star rated. If you have a budget, click on how much you'd like to spend and then browse our incredible deals. We'll help you find the perfect fit whatever your trip looks like.
How can I find cheap condos in Cow Key?
With Expedia's filter tool, getting your hands on cheap condos in Cow Key is easy. To find stays that'll make your wallet smile, narrow down your search by amenities, budget and star rating.

Explore a world of travel with Expedia