Cow Key Holiday Rentals, Key West: Private House Rentals

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

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

A bar area with a thatched roof, wooden chairs, and a poolside view.

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

1. Hampton Inn Key West FL

Key West

Erika

฿5,649

฿6,355 total

includes taxes & fees

27 Oct - 28 Oct

A pool area with lounge chairs and umbrellas, surrounded by palm trees.

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.

A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.

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

New Town

Brian

฿3,899

฿5,331 total

includes taxes & fees

26 Oct - 27 Oct

A hotel with a central fountain, surrounded by palm trees and a well-maintained lawn.

A balcony with a view of a pool area, palm trees, and outdoor seating.

A hotel room with a bed, a nightstand with a drawer, a wall-mounted lamp, and a patterned curtain.

A hotel room with a sofa, a small table, a lamp, and a balcony with chairs.

3. DoubleTree Resort by Hilton Grand Key - Key West

Key West

Danee

฿3,869

฿5,486 total

includes taxes & fees

28 Oct - 29 Oct

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 swimming pool, and palm trees.

A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

4. The Perry Hotel & Marina Key West

Stock Island

Jade

฿3,220

฿5,587 total

includes taxes & fees

16 Nov - 17 Nov

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

5. Blue Flamingo Resort Key West

New Town

Terra

฿4,181

฿6,585 total

includes taxes & fees

25 Oct - 26 Oct

A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.

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.

A pool area with lounge chairs, palm trees, and a building with a tiled roof.

6. Courtyard by Marriott Key West Waterfront

Northside Resort

Everton

฿5,314

฿5,979 total

includes taxes & fees

27 Oct - 28 Oct

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 spacious lobby with a marble floor, leather sofas, and large potted plants.

7. Beachside Resort & Residences

Key West

Deana

฿3,910

฿7,595 total

includes taxes & fees

27 Oct - 28 Oct

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 bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'

8. Hilton Garden Inn Key West / The Keys Collection

New Town

Eli

฿3,551

฿4,940 total

includes taxes & fees

28 Oct - 29 Oct

A hotel with a covered entrance, multiple balconies, and palm trees.

A waterfront hotel with multiple balconies, a dock, and boats.

A covered balcony with white Adirondack chairs and a small table with flowers, overlooking a turquoise sea and distant shoreline.

A restaurant interior with wooden beams, a bar area, and a colorful ceiling mural.

9. Opal Key Resort & Marina, Key West

Old Town Key West

Ann

฿8,657

฿11,055 total

includes taxes & fees

26 Oct - 27 Oct

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

A swimming pool surrounded by palm trees and lounge chairs, with a clear view of the ocean in the background.

10. Hyatt Vacation Club at Windward Pointe, Key West

Key West

Leismy

฿6,197

฿8,475 total

includes taxes & fees

26 Oct - 27 Oct

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

A beach with palm trees, lounge chairs, and umbrellas.

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, a sandy shore, and a calm sea under a clear sky.

11. Parrot Key Hotel & Villas

Northside Resort

Anthony

฿5,105

฿7,670 total

includes taxes & fees

29 Oct - 30 Oct

A wooden deck with wicker furniture and a glass balustrade overlooking a beach.

A resort with a pool leading to a beach, surrounded by palm trees and white buildings.

A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.

A beach with white lounge chairs and umbrellas, a sandy shore, and a calm sea under a partly cloudy sky.

12. Casa Marina Key West, Curio Collection by Hilton

Old Town Key West

Robert

฿7,500

฿10,694 total

includes taxes & fees

27 Oct - 28 Oct

A hotel with a swimming pool, balconies, and a view of the sea.

A balcony with a view of the ocean, a table, chairs, and a railing.

A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.

A beach wedding setup with white chairs, a wooden arch, and lanterns.

13. Hyatt Centric Key West Resort and Spa

Key West Historic District

Joseph

฿7,821

฿11,130 total

includes taxes & fees

25 Oct - 26 Oct

A beach with a wooden pier, palm trees, and beach umbrellas.

An outdoor dining area with tables and chairs, overlooking the ocean.

A modern bar area with a central island, white bar stools, and a view of the ocean.

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

14. The Reach Key West, Curio Collection by Hilton

Old Town Key West

Brett

฿5,334

฿8,268 total

includes taxes & fees

28 Oct - 29 Oct

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

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

A hotel with a pool, bicycles, and lush greenery.

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.

15. Silver Palms Inn & Historic Homes

Old Town Key West

sam

฿2,978

฿5,607 total

includes taxes & fees

25 Oct - 26 Oct

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

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

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.

16. Ibis Bay Beach Resort

Northside Resort

Andre

฿3,603

฿5,137 total

includes taxes & fees

21 Oct - 22 Oct

A marina with boats docked, a pool area, and a building with a white facade.

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

A marina with numerous boats docked, a swimming pool, and palm trees.

A covered outdoor seating area with tables and chairs, overlooking a marina with boats.

17. Hilton Key West Resort & Marina

Stock Island

Eric A

฿3,966

฿6,426 total

includes taxes & fees

28 Oct - 29 Oct

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.

18. Hyatt Vacation Club at Beach House, Key West

Key West

Rachel

฿6,919

฿9,288 total

includes taxes & fees

29 Oct - 30 Oct

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

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

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

A beach with a palm tree and two chairs.

19. Margaritaville Beach House Key West

Key West

Siamak

฿6,986

฿9,968 total

includes taxes & fees

19 Nov - 20 Nov

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

A bar setting with a bartender preparing a drink, a counter with various bottles, and a TV screen in the background.

A spacious lobby with a central seating area, two staircases, and multiple potted plants.

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

20. Havana Cabana at Key West

New Town

Stephanie

฿4,836

฿7,573 total

includes taxes & fees

3 Nov - 4 Nov

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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 wooden signpost with directional arrows pointing to various cities and distances.

A beach with two wooden lounge chairs and a straw umbrella.

A wooden pathway leading to a beach with seagulls flying over the water.

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.

Beachside

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

See properties

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.

See properties

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

The Southernmost Inn - Adults Only

10/10 Excellent

"Great place."

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

10/10 Excellent

"For me 10 of 100 great hotel very clean and very good room omg super nice , breakfast very good ."

Casa Marina Key West, Curio Collection by Hilton

8/10 Good

"Great location on the water"

Margaritaville Beach House Key West

8/10 Good

"Air conditioning in the rooms are wonderful. Our shower broke, front desk quickly got us a new room. Bartender Levan was Great!!! He’s very attentive and makes tasty drinks. We would stay here again."

Havana Cabana at Key West

10/10 Excellent

"Enjoyed my stay. Staff was nice and friendly. Bartender at Flama Cabana was awesome."

Beachside Resort & Residences

8/10 Good

"Friendly clean facilities!!!"

Hilton Garden Inn Key West / The Keys Collection

8/10 Good

"Pros: great location, nice pool area, clean room, price good for the area, friendly staff. Cons: ice machine near our room broken, one of the elevators was out of order, bed uncomfortably firm, despite the website saying they had dinner inside the only food choices were from the poolside bar. Still waiting on the itemized bill, believe we were overcharged on “extras”."

DoubleTree Resort by Hilton Grand Key - Key West

10/10 Excellent

"Limpio .buena atención. Transporte rápido para el centro y playa parqueo incluido para muchos carros"

Blue Flamingo Resort Key West

10/10 Excellent

"Very nice place to stay they even offer a shuttle bus to duval"

More cheap stays in Cow Key

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

฿3,603

฿5,137 total

21 Oct - 22 Oct

includes taxes & fees

8.2/10 Very good! (2,409 reviews)

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL

฿5,649

฿6,355 total

27 Oct - 28 Oct

includes taxes & fees

9/10 Wonderful! (1,565 reviews)

Southwinds Motel

1321 Simonton Street Key West FL

฿4,668

฿6,385 total

26 Oct - 27 Oct

includes taxes & fees

8.6/10 Excellent! (1,387 reviews)

Alexander Palms Court

715 South St Key West FL

฿6,015

฿6,767 total

21 Oct - 22 Oct

includes taxes & fees

Pegasus International Hotel

501 Southard Street Key West FL

฿6,015

฿8,467 total

25 Oct - 26 Oct

includes taxes & fees

Tranquility Guest House

302 Angela st Key West FL

฿5,621

฿9,309 total

27 Oct - 28 Oct

includes taxes & fees

9/10 Wonderful! (37 reviews)

Frequently asked questions

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

Blue Flamingo Resort Key West, located 1.2 mi (1.9 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 Southernmost Beach Resort and Guesthouses and Margaritaville Beach House 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 3049 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 Key West Tropical Forest and Botanical Garden and Stock Island Yacht Club & Marina 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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Find hotels in Cow Key, FL from ฿4,940

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. Hampton Inn Key West FL

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

3. DoubleTree Resort by Hilton Grand Key - Key West

4. The Perry Hotel & Marina Key West

5. Blue Flamingo Resort Key West

6. Courtyard by Marriott Key West Waterfront

7. Beachside Resort & Residences

8. Hilton Garden Inn Key West / The Keys Collection

9. Opal Key Resort & Marina, Key West

10. Hyatt Vacation Club at Windward Pointe, Key West

11. Parrot Key Hotel & Villas

12. Casa Marina Key West, Curio Collection by Hilton

13. Hyatt Centric Key West Resort and Spa

14. The Reach Key West, Curio Collection by Hilton

15. Silver Palms Inn & Historic Homes

16. Ibis Bay Beach Resort

17. Hilton Key West Resort & Marina

18. Hyatt Vacation Club at Beach House, Key West

19. Margaritaville Beach House Key West

20. Havana Cabana at Key West

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

The Southernmost Inn - Adults Only

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

Casa Marina Key West, Curio Collection by Hilton

Margaritaville Beach House Key West

Havana Cabana at Key West

Beachside Resort & Residences

Hilton Garden Inn Key West / The Keys Collection

DoubleTree Resort by Hilton Grand Key - Key West

Blue Flamingo Resort Key West

More cheap stays in Cow Key

Ibis Bay Beach Resort

Hampton Inn Key West FL

Southwinds Motel

Alexander Palms Court

Pegasus International Hotel

Tranquility Guest House

Frequently asked questions

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