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

Find All Inclusive Resorts and Hotels in Cow Key, FL

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Cow Key All Inclusive Resorts and Hotels

Tonight
Oct 18 - Oct 19
Tomorrow
Oct 19 - Oct 20
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
No exact matches found, but these alternatives could be just right

Recommended hotels in Cow Key

A balcony with a view of a pool area, palm trees, and outdoor seating.
A modern living room with a desk, two chairs, a sofa, and a TV mounted on the wall.
A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.
A modern room with a white cabinet, a flat-screen TV, a small table, and a bench.

1. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
CA $169
CA $237 total
includes taxes & fees
Oct 25 - Oct 26
DoubleTree Resort by Hilton Grand Key - Key West
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.
A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.
A marina with boats docked, a swimming pool, and palm trees.

2. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
CA $122
CA $223 total
includes taxes & fees
Nov 2 - Nov 3
The Perry Hotel & Marina Key West
A swimming pool with lounge chairs and palm trees.
A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.
Sports facility
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

3. Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
CA $150
CA $208 total
includes taxes & fees
Oct 28 - Oct 29
Hilton Garden Inn Key West / The Keys Collection
A pool area with lounge chairs and umbrellas, surrounded by palm trees.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.
A modern office space with a reception desk, computer, and seating area.
A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

4. Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
CA $177
CA $239 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Pool
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.

5. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
CA $177
CA $279 total
includes taxes & fees
Oct 25 - Oct 26
Blue Flamingo Resort Key West
A balcony with wicker furniture, a view of the sea, and a spiral staircase.
A spacious lobby with a marble floor, leather sofas, and large potted plants.
A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.
A modern dining area with a glass table, four chairs, and a ceiling fan.

6. Beachside Resort & Residences

Beachside Resort & Residences
Key West
CA $165
CA $321 total
includes taxes & fees
Oct 27 - Oct 28
Beachside Resort & Residences
A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.
A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean in the background.
A beach volleyball court with a net, surrounded by palm trees and a hotel in the background.
A resort with a well-maintained lawn, palm trees, a pool area, and a view of the ocean.

7. Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West
Key West
CA $242
CA $336 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Vacation Club at Windward Pointe, Key West
A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.
A hotel room with two beds, a balcony with a view of the ocean, and a large wave painting on the wall.
A modern kitchen with white cabinets and a built-in microwave. There is a dining area with a table set for two, a sofa, and a balcony with a view of the ocean.
A multi-story hotel with balconies and a well-lit entrance.

8. The Laureate Key West

The Laureate Key West
New Town
CA $225
CA $293 total
includes taxes & fees
Oct 19 - Oct 20
The Laureate Key West
A wooden archway leading to a pool area surrounded by lush tropical vegetation.
A large, two-story building with a symmetrical facade, a central entrance with a double door, and a balcony on the upper floor.
A beach with palm trees, lounge chairs, and umbrellas.
A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

9. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
CA $215
CA $323 total
includes taxes & fees
Oct 29 - Oct 30
Parrot Key Hotel & Villas
A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.
A pool area with lounge chairs, palm trees, and a building with a tiled roof.
A modern restaurant with a wooden counter, seating area, and large windows.
A hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.

10. Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
Northside Resort
CA $225
CA $253 total
includes taxes & fees
Oct 27 - Oct 28
Courtyard by Marriott Key West Waterfront
View all properties

Choose what matters most at all-inclusive hotels in Cow Key

5 stars
4 stars
Adult-only
Pool
Family-friendly

Top Cow Key Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

8/10 Good
"the ice maker on the first floor was broken the whole time. the housekeeping was inconsistent, sometimes we would get cups, sometimes not. same cigarette butt on the patio all 4 days. The pool was dirty and had tiles missing. The music our first night was loud and shook the room until 10:30pm. It was a little disappointing. The location and view was good."
Lynn 4-night trip
Posted less than an hour ago
Casa Marina Key West, Curio Collection by Hilton

Frequently asked questions

Looking for Cow Key all-inclusive resorts?
View our choice of all-inclusive accommodations where you can enjoy a host of amenities such as entertainment, kid's clubs, and of course food and beverages all included in your stay. Many of our all-inclusive hotel accommodations also feature activities such as golf, yoga, water sports, and more, which you can enjoy without any additional expense.
What is there to do near my all-inclusive resort in Cow Key?
If you want to explore the area around your all-inclusive resort, visit Duval Street and Florida Keys Beaches and see why travelers like Cow Key! Other attractions include Key West Tropical Forest and Botanical Garden, Stock Island Yacht Club & Marina, and Key West Golf Club.
When's the best time for an all-inclusive stay in Cow Key?
There's nothing like an all-inclusive vacation in Cow Key to refresh you, especially when you know what to expect from the elements. Here's some info to help you decide when to book: The hottest months are usually August and July with an average temp of 84°F, while the coldest months are January and February with an average of 73°F. March and February are the driest months while September and October are the rainiest months.

Explore a world of travel with Expedia