𝗧𝗢𝗣 𝟭𝟬 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Cow Key (2026)

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

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Our top choices for Cow Key hotels

A balcony with wicker furniture, a view of the sea, and a spiral staircase.

A modern dining area with a glass table, four chairs, and a ceiling fan.

A beach with palm trees, clear blue water, and a pier extending into the sea.

A swimming pool with lounge chairs and palm trees, overlooking a sunset over the water.

1. Beachside Resort & Residences

Key West

Jerome

S$275

includes taxes & fees

1 Sept - 2 Sept

A clear view of turquoise ocean water and a blue sky with clouds.

A breakfast setting with a table, chairs, a vase with flowers, and a city view.

A hotel room with a balcony overlooking a marina and the ocean.

2. Hilton Key West Resort & Marina

Stock Island

Linda

S$240

includes taxes & fees

7 Sept - 8 Sept

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.

A hotel room with a balcony, a bed, a desk, and two chairs.

A modern kitchen with a marble island, wooden cabinets, and pendant lighting.

A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.

3. Hampton Inn Key West FL

Key West

Melisa

S$199

includes taxes & fees

1 Sept - 2 Sept

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.

An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.

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

New Town

Fernando

S$202

includes taxes & fees

20 Sept - 21 Sept

A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.

A spacious living area with a high ceiling, a blue accent wall, and a wooden staircase.

A hotel with a central courtyard, palm trees, and a fountain.

An outdoor patio with tables and chairs, umbrellas, and palm trees.

5. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Jose

S$206

includes taxes & fees

7 Sept - 8 Sept

A swimming pool with lounge chairs and palm trees.

A covered outdoor seating area with a central bar, patterned chairs, and a decorative sign.

A modern living room with a sectional sofa, a small round table, and a potted plant.

6. Hilton Garden Inn Key West / The Keys Collection

New Town

Amanda

S$193

includes taxes & fees

22 Sept - 23 Sept

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

A marina with boats docked, a building with multiple floors, and palm trees in the background.

A marina with numerous yachts docked, surrounded by palm trees and a clear sky.

7. The Perry Hotel & Marina Key West

Stock Island

Boyan

S$281

includes taxes & fees

21 Sept - 22 Sept

A hotel with a large pool, multiple balconies, and palm trees.

A couple holding hands in a tropical setting with palm trees and greenery.

A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.

8. Blue Flamingo Resort Key West

New Town

Sabrina

S$238

includes taxes & fees

1 Sept - 2 Sept

A dining table with plates of food, a drink, and a view of a pool and palm trees.

A beach with a palm tree and two chairs.

A hotel room with a bed, a TV, a coffee table, a sofa, and a view of the ocean.

A person standing by a window overlooking a beach with palm trees and the ocean.

9. Margaritaville Beach House Key West

Key West

TRICIA LYNN

S$335

includes taxes & fees

13 Sept - 14 Sept

A hotel room with a bed, a view of the beach, a hammock, and beach chairs.

A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.

A marina with boats docked, a beach resort building, and palm trees.

A pool area with blue lounge chairs, a hot tub, and a covered seating area.

10. Ibis Bay Beach Resort

Northside Resort

Roland

S$195

includes taxes & fees

1 Sept - 2 Sept

A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

A two-story building with a central entrance, surrounded by palm trees and a wooden walkway.

A resort with a well-maintained lawn, palm trees, a pool area, and a view of the ocean.

A beach volleyball court with a net, surrounded by palm trees and a hotel in the background.

11. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Mauricio

S$300

includes taxes & fees

15 Sept - 16 Sept

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.

12. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

S$249

includes taxes & fees

29 Sept - 30 Sept

Two wooden Adirondack chairs on a sandy beach with a view of the sea and a sailboat in the distance.

A poolside lounge area with a wicker chair, a straw hat, and a beach bag.

A two-story building with a balcony, arched windows, and a green roof.

A wooden deck with two wooden chairs and a small table, surrounded by white railings and palm trees.

13. Hyatt Vacation Club at Beach House, Key West

Key West

Kailey

S$341

includes taxes & fees

19 Sept - 20 Sept

A wooden archway leading to a pool area surrounded by lush tropical vegetation.

A beach with palm trees, a sandy shore, and a calm sea under a clear sky.

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.

14. Parrot Key Hotel & Villas

Northside Resort

Melvin

S$307

includes taxes & fees

14 Sept - 15 Sept

A swimming pool with water splashing, surrounded by palm trees and a building in the background.

The entrance to Silver Palms Inn with a reception desk, a seating area, and a glass door.

The exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.

A two-story yellow house with a porch, white railings, and green shutters.

15. Silver Palms Inn & Historic Homes

Old Town Key West

Shawn

S$181

includes taxes & fees

1 Sept - 2 Sept

A covered porch with wicker furniture, potted plants, and a sign for the "Office" at the Palm Hotel.

A hotel with a white facade, multiple balconies, and lush tropical landscaping.

A row of bicycles parked in front of a building with a white balcony and a palm tree.

A pink building with a white door, a balcony with a white railing, and a view of a pool area.

16. The Palms Hotel

Old Town Key West

John

S$175

includes taxes & fees

16 Sept - 17 Sept

A swimming pool surrounded by palm trees and a natural rock formation.

A cozy room with wicker furniture, a glass coffee table, and a view of lush greenery outside.

An outdoor dining area with round tables and chairs, surrounded by greenery and a mural.

17. Havana Cabana at Key West

New Town

Fabrizio

S$280

includes taxes & fees

2 Sept - 3 Sept

A building with a white exterior, a large red awning, and a gated entrance.

A small, enclosed porch with a chair and a table, surrounded by lush greenery and a white lattice fence.

A spacious kitchen with a dining area, large windows, and a view of the outdoors.

A pool area with lounge chairs and a lifebuoy.

18. Authors of Key West Guest House

Key West Historic District

Kasi

S$128

includes taxes & fees

3 Sept - 4 Sept

A spacious living room with a balcony, a ceiling fan, and a large window offering a view of the ocean.

A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean at dusk.

A multi-story hotel with balconies and a well-lit entrance.

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.

19. The Laureate Key West

New Town

Jayce

S$264

includes taxes & fees

1 Sept - 2 Sept

A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

A two-story building with a white picket fence, a mailbox, and a small tree in front.

A hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.

A lush garden with a variety of tropical plants and a paved walkway.

20. Duval House

Old Town Key West

Timothy

S$155

includes taxes & fees

1 Sept - 2 Sept

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Explore the area near Cow Key and other popular areas in Key West

Find the best Cow Key areas for the activities you enjoy most.

A palm tree on a sandy beach with clear blue water and a bright blue sky.

A coastal scene with a long bridge over turquoise waters, a sandy beach, and a palm tree.

A palm tree on a sandy beach with a clear blue sky and ocean.

A beach with palm trees, clear blue sky, and calm sea.

Beachside

If you're spending some time in Beachside, Florida Keys Beaches and Smathers Beach are top sights worth seeing.

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A beach with rocky shoreline, palm trees, and a sailboat in the distance.

White St. Gallery

If you're looking for some top things to see and do in White St. Gallery and surrounding area, you can visit Duval Street and Clarence S. Higgs Memorial Beach Park.

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A white building with a large arched entrance and multiple windows.

White Street Gallery District

If you're looking for some top things to see and do in White Street Gallery District and surrounding area, you can visit Duval Street and Clarence S. Higgs Memorial Beach Park.

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Learn more about Cow Key

Just a short drive from the vibrant Duval Street, this tranquil key offers easy access to Key West's tropical botanical garden. Spend your days lounging at nearby Smathers Beach or exploring the Stock Island Yacht Club & Marina with its charming waterfront views.

See all hotels in Cow Key

Top Cow Key Hotel Reviews

Southwinds Motel

8/10 Good

"Enjoyed the stay, still a great location, experience, and value."

Beachside Resort & Residences

10/10 Excellent

"Room was clean, exactly what we had hoped for. Staff was friendly and helpful!"

Casa Marina Key West, Curio Collection by Hilton

8/10 Good

"Everything was great except the beds they were pretty uncomfortable. Expected better for a resort."

Pier House Resort & Spa

10/10 Excellent

"Best Hotel in the Key West. Room was very clean, best staff services. Beautiful beach view and breakfast was delicious. My husband and I love this place. 💯 recommend."

Blue Flamingo Resort Key West

10/10 Excellent

"Clean, comfortable. Pools were excellent and a super nice and helpful staff."

Hampton Inn Key West FL

10/10 Excellent

"My family and I enjoyed our stay! It was very clean complementary breakfast was yummy and the pool was beautiful! Definitely try the blackened mahi mahi sandwich!!"

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Check-in was easy, and the front desk staff were extremely kind and accommodating. We thought they were wonderful. Our only complaint was an unfortunate incident with another staff member. A middle-aged woman in a green shirt, wearing earbuds/headphones, was riding a motorized mobility scooter through the hallway and ran over my daughter’s foot. We believe she may have been moving the scooter from one location to another, as we saw her walking normally later that evening. She simply said “oops” and continued on without apologizing or stopping to make sure my daughter was okay. Her foot is now badly bruised and very sore. We found her response incredibly inconsiderate and rude, particularly toward a child. Management should address this with the employee, as this is not an appropriate way to treat hotel guests."

The Reach Key West, Curio Collection by Hilton

10/10 Excellent

"Had an issue with the door on the last day, but they rectified the problem. Stay was quite pleasant. Enjoyed immensely will be back in January."

Hyatt Centric Key West Resort and Spa

10/10 Excellent

"Loved the location overall 100%"

More cheap stays in Cow Key

Simonton Court Historic Inn & Cottages

523 Eaton Street Key West FL

S$185

1 Sept - 2 Sept

includes taxes & fees

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

S$195

1 Sept - 2 Sept

includes taxes & fees

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

S$199

1 Sept - 2 Sept

includes taxes & fees

9/10 Wonderful! (1,486 reviews)

Southwinds Motel

1321 Simonton Street Key West FL

S$217

7 Sept - 8 Sept

includes taxes & fees

8.6/10 Excellent! (1,368 reviews)

Tranquility Guest House

302 Angela st Key West FL

S$232

22 Sept - 23 Sept

includes taxes & fees

Weatherstation Inn

57 Front St Key West FL

S$242

1 Sept - 2 Sept

includes taxes & fees

9.4/10 Exceptional! (1,002 reviews)

Frequently asked questions

What's the best place to stay in Cow Key?

Southernmost Beach Resort and Guesthouses, located 3.6 mi (5.7 km) from the heart of Cow Key, is a top choice for your stay, based on our traveller data. Other good options for your visit to the area are Ibis Bay Beach Resort and Havana Cabana at Key West. See all available top hotels, or vacation rentals in Cow Key.

What are some of the best holiday rentals that Cow Key has to offer?

Sugarloaf Key RV Resort & Cottages: This holiday home rental outside of Cow Key is located near a metro station, and offers an outdoor pool, air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind. See all vacation rentals in Cow Key.

If I need to cancel my hotel reservation in Cow Key, will I receive a refund?

Yes! You'll find that most room reservations are refundable if you cancel prior to the hotel's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a reservation that's non-refundable, it may still be possible to cancel it and receive a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Cow Key.

How is it staying in Cow Key?

Visitors can enjoy all that Cow Key has to offer, including the restaurants, shopping and beaches. Top sights around the area include Duval Street and Florida Keys Beaches. There are 3045 hotels and other accommodation options in the surrounding area. Find out more about Cow Key.

What should I see while I'm in Cow Key?

Notable places to visit in the surrounding area include Duval Street and Florida Keys Beaches. You'll also find Robbie's and Key West Tropical Forest and Botanical Garden in the area. Take a look at what more there is to see and do in Expedia's Cow Key guide.

What's the seasonal weather in Cow Key?

The hottest months are usually August and July, with an average temperature of 29°C, while the coldest months are January and February, with an average of 23°C. Average annual precipitation for Cow Key is 956 mm.

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Fort East Martello Museum and Gallery

Cow Key Hotels from S$128

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Cow Key

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Cow Key hotels

1. Beachside Resort & Residences

2. Hilton Key West Resort & Marina

3. Hampton Inn Key West FL

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

5. DoubleTree Resort by Hilton Grand Key - Key West

6. Hilton Garden Inn Key West / The Keys Collection

7. The Perry Hotel & Marina Key West

8. Blue Flamingo Resort Key West

9. Margaritaville Beach House Key West

10. Ibis Bay Beach Resort

11. Hyatt Vacation Club at Windward Pointe, Key West

12. Courtyard by Marriott Key West Waterfront

13. Hyatt Vacation Club at Beach House, Key West

14. Parrot Key Hotel & Villas

15. Silver Palms Inn & Historic Homes

16. The Palms Hotel

17. Havana Cabana at Key West

18. Authors of Key West Guest House

19. The Laureate Key West

20. Duval House

Explore the area near Cow Key and other popular areas in Key West

Beachside

White St. Gallery

White Street Gallery District

Learn more about Cow Key

Top Cow Key Hotel Reviews

Southwinds Motel

Beachside Resort & Residences

Casa Marina Key West, Curio Collection by Hilton

Pier House Resort & Spa

Blue Flamingo Resort Key West

Hampton Inn Key West FL

DoubleTree Resort by Hilton Grand Key - Key West

The Reach Key West, Curio Collection by Hilton

Hyatt Centric Key West Resort and Spa

More cheap stays in Cow Key

Simonton Court Historic Inn & Cottages

Ibis Bay Beach Resort

Hampton Inn Key West FL

Southwinds Motel

Tranquility Guest House

Weatherstation Inn

Frequently asked questions

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