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

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Check availability on Cow Key Luxury Hotels

Tonight
Sep 4 - Sep 5
Tomorrow
Sep 5 - Sep 6
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Cow Key luxury hotels

A clear swimming pool with lounge chairs and gazebos, surrounded by palm trees.
A hotel with a central courtyard, palm trees, and a fountain.
A spacious living area with a high ceiling, a blue accent wall, and a wooden staircase.
A spacious indoor dining area with tables and chairs, ceiling fans, and large windows.

1. DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
NT$3,491
NT$5,000 total
includes taxes & fees
Sep 15 - Sep 16
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 marina with numerous yachts docked, surrounded by palm trees and a clear sky.
An outdoor seating area with tables and chairs, overlooking a marina with boats.
A marina with boats docked, a building with multiple floors, and palm trees in the background.

2. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
NT$4,479
NT$6,996 total
includes taxes & fees
Sep 21 - Sep 22
The Perry Hotel & Marina Key West
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 hotel room with a balcony overlooking a marina and the ocean.
A marina with numerous boats docked, a swimming pool, and palm trees.

3. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
Stock Island
  • Waterfront luxury meets marina adventure at Key West resort with 6 pools and bayside elegance.
NT$3,618
NT$5,968 total
includes taxes & fees
Sep 16 - Sep 17
Hilton Key West Resort & Marina
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 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.

4. Margaritaville Beach House Key West

Margaritaville Beach House Key West
Key West
NT$5,650
NT$8,348 total
includes taxes & fees
Sep 17 - Sep 18
Margaritaville Beach House Key West
A hotel with a large pool, multiple balconies, and palm trees.
A spacious living area with a sofa, chairs, a coffee table, and a foosball table. Large windows offer a view of the outdoor area.
A hotel room with a bed, a sofa, a round table with a book, a window with a view, and a radiator.
A modern cafe with a wooden counter, seating area, and shelves stocked with beverages.

5. Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
New Town
NT$3,481
NT$5,701 total
includes taxes & fees
Sep 8 - Sep 9
Blue Flamingo Resort Key West
A wooden deck with wicker furniture and a glass balustrade overlooking a beach.
A beachside spa with two massage tables under a canopy, overlooking the sea and a pier.
A spacious lobby with green sofas, a coffee table, and a dining area.
A resort with a pool leading to a beach, surrounded by palm trees and white buildings.

6. Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
Old Town Key West
  • Beachfront luxury graces historic Key West resort with private shore access and spa treatments.
NT$6,641
NT$9,616 total
includes taxes & fees
Sep 6 - Sep 7
Casa Marina Key West, Curio Collection by Hilton
A pool area with lounge chairs and palm trees.
A hotel named "Santa Maria" with a prominent illuminated sign, a glass entrance, and a view of the ocean.
A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.
A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.

7. Santa Maria Suites

Santa Maria Suites
Old Town Key West
  • Lavish Key West retreat features luxury suites, designer touches, 2 pools, and vibrant bar scene.
NT$8,856
NT$12,106 total
includes taxes & fees
Sep 7 - Sep 8
Santa Maria Suites
A beachfront hotel with a covered patio, palm trees, and a boat on the sand.
A view through a white-framed window with a decorative white fence, leading to a tiled patio area with a round table.
A resort with a beach, a dock, and a water view.
A balcony with a view of the ocean, a sofa, and a massage table.

8. Pier House Resort & Spa

Pier House Resort & Spa
Key West Historic District
NT$9,212
NT$12,580 total
includes taxes & fees
Sep 10 - Sep 11
Pier House Resort & Spa
A wooden archway leading to a pool area surrounded by lush tropical vegetation.
A tall palm tree with a white building in the background.
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.

9. Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
Northside Resort
NT$4,190
NT$6,535 total
includes taxes & fees
Sep 15 - Sep 16
Parrot Key Hotel & Villas
A two-story building with a covered entrance, palm trees, and a bench outside.
A white building with a sign reading 'Kimpton Key West Winslow's Bungalow.'
A poolside area with lounge chairs, umbrellas, and a covered seating area with hanging lights.
A bright room with a staircase, two windows overlooking a pool area, and two wicker chairs with cushions.

10. Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
Old Town Key West
NT$6,190
NT$8,571 total
includes taxes & fees
Sep 8 - Sep 9
Winslow's Bungalows - Key West Historic Inns
View all properties

Top Cow Key Hotel Reviews

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

10/10 Excellent
"Clean room"
Luis 2-night trip
Posted 3 hours ago
Casa Marina Key West, Curio Collection by Hilton
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

10/10 Excellent
"Very happy with our stay!"
David 2-night trip
Posted 4 hours ago
Parrot Key Hotel & Villas
Ibis Bay Beach Resort

Ibis Bay Beach Resort

10/10 Excellent
"Greater beach hotel just outside the main strip but very easy uber ride Hotel right on a small beach great pool and seafood restaurant and small zoo for the children too"
Stephen 2-night trip
Posted 8 hours ago
Ibis Bay Beach Resort
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

10/10 Excellent
"Staff was very helpful and nice"
Cheri 5-night trip
Posted 9 hours ago
The Reach Key West, Curio Collection by Hilton
Hampton Inn Key West FL

Hampton Inn Key West FL

10/10 Excellent
"Nice property. Very pleasant stay."
Cynthia 1-night trip
Posted 10 hours ago
Hampton Inn Key West FL
Southwinds Motel

Southwinds Motel

8/10 Good
"Great location. Nice pool. Parking. Thirsty Rooster 🐓 bar out front was so much fun and a great vibe. Not to mention a close distance to Duval St. Where the action is. Deli and groceries across the street as well. We will be back"
Brian 1-night trip
Posted 10 hours ago
Southwinds Motel
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

8/10 Good
"Liked everything but restaurant prices were extremely high for breakfast. Outrageous breakfast prices for simple breakfast. Cannot recommend restaurant."
Dennis 3-night trip
Posted 17 hours ago
Hilton Key West Resort & Marina
Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"Great location. Staff were very nice. Room clean. Food good."
David 5-night trip
Posted 20 hours ago
Pier House Resort & Spa
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

10/10 Excellent
"The staff were outstanding, especially Anna at the front desk. They all were so warm and welcoming. The rooms were spacious and clean. The pool was clean and mostly quiet (which was nice and relaxing)."
sharon 3-night trip
Posted 2 days ago
Hyatt Centric Key West Resort and Spa

Frequently asked questions

Are you searching for the perfect hotel for your luxury getaway to Cow Key?
Use Expedia to arrange your flight to Key West Intl. Airport (EYW) airport, and then select from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you'd like to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can assist you in finding the best luxury hotel experience that Cow Key offers.
When can I expect good weather in Cow Key?
Planning for the weather is a good way to make your trip to Cow Key relaxing and enjoyable, especially when you're splurging. 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. Average annual precipitation for Cow Key is 38 inches.
What's there to see and do in Cow Key?
Enjoy all that Cow Key has to offer when you visit Duval Street, Florida Keys Beaches, and Robbie's. If you have a bit of extra time while you're in the area, you might want to check out Key West Tropical Forest and Botanical Garden and Stock Island Yacht Club & Marina.

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