Cow Key Hotel Guide - 4 Stars Hotels in Cow Key, Key West

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Check availability on Cow Key 4 Star Hotels

Tonight
25 Dec - 26 Dec
Tomorrow
26 Dec - 27 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Cow Key 4-star hotels

2 outdoor pools, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West
4.0 star property
New Town
8.0 out of 10, Very good, (1797)
"the staff was so welcoming and nice, it was a perfect place to stay in Key West!"
United Kingdom
Alicia
The price is Rp3.907.921
Rp5.339.442 total
includes taxes & fees
8 Jan - 9 Jan 2026
Blue Flamingo Resort Key West
3 outdoor pools, pool umbrellas, pool loungers
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses
4.0 star property
Old Town Key West
8.8 out of 10, Excellent, (2950)
"Wonderful stay!"
United States
Elisa
The price is Rp4.950.034
Rp6.794.812 total
includes taxes & fees
13 Jan - 14 Jan 2026
Southernmost Beach Resort and Guesthouses
Exterior
Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
4.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1002)
"Staff was courteous and the location is perfect for a weekend in Key West."
United States
TIMOTHY
The price is Rp6.689.235
Rp8.619.305 total
includes taxes & fees
12 Jan - 13 Jan 2026
Hyatt Centric Key West Resort and Spa
6 outdoor pools, free pool cabanas, pool umbrellas
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina
4.0 star property
Stock Island
8.8 out of 10, Excellent, (1758)
"The place is great!"
United States
Anna
The price is Rp4.097.534
Rp5.636.561 total
includes taxes & fees
8 Jan - 9 Jan 2026
Oceans Edge Key West Resort, Hotel & Marina
Beach nearby, white sand
Margaritaville Beach House Key West

Margaritaville Beach House Key West

Margaritaville Beach House Key West
4.0 star property
Key West
8.8 out of 10, Excellent, (1775)
"Nice spot and great staff"
United States
Lindsay Brooke
The price is Rp5.985.105
Rp7.819.049 total
includes taxes & fees
8 Jan - 9 Jan 2026
Margaritaville Beach House Key West
2 outdoor pools, open 8:00 AM to 10:00 PM, pool loungers
The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
4.0 star property
Stock Island
9.4 out of 10, Exceptional, (1173)
"great place to stay "
United States
michael
The price is Rp4.486.848
Rp6.080.105 total
includes taxes & fees
11 Jan - 12 Jan 2026
The Perry Hotel & Marina Key West
Outdoor pool, open 7:00 AM to 11:00 PM, pool cabanas (surcharge)
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
4.0 star property
Key West
8.2 out of 10, Very good, (1000)
"Nice property, comfortable stay - cookies and staff are great!"
United States
David
The price is Rp4.010.188
Rp5.077.280 total
includes taxes & fees
4 Jan - 5 Jan 2026
DoubleTree Resort by Hilton Grand Key - Key West
4 outdoor pools, pool umbrellas, pool loungers
Parrot Key Hotel & Villas

Parrot Key Hotel & Villas

Parrot Key Hotel & Villas
4.0 star property
Northside Resort
9.0 out of 10, Wonderful, (1212)
"Great location - nice pools - excellent staff"
United States
Gary
The price is Rp3.690.815
Rp5.114.143 total
includes taxes & fees
8 Jan - 9 Jan 2026
Parrot Key Hotel & Villas
3 outdoor pools, open 7:00 AM to 10:00 PM, pool loungers
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns
4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1087)
"Beautiful property, nice clean bungalows and great staff!"
United States
Robert
The price is Rp6.021.988
Rp7.623.549 total
includes taxes & fees
14 Jan - 15 Jan 2026
Winslow's Bungalows - Key West Historic Inns
Fireplace
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton
4.0 star property
Old Town Key West
8.4 out of 10, Very good, (485)
"Clean, great staff and location."
United States
Vincent
The price is Rp7.547.268
Rp9.496.577 total
includes taxes & fees
12 Jan - 13 Jan 2026
Casa Marina Key West, Curio Collection by Hilton
Exterior
La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection

La Concha Key West, Autograph Collection
4.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (297)
"Very nice staff! Clean hotel! "
United States
Tabitha Hall
The price is Rp5.690.793
Rp6.968.703 total
includes taxes & fees
7 Jan - 8 Jan 2026
La Concha Key West, Autograph Collection
Private beach, white sand, sun-loungers, beach umbrellas
Pier House Resort & Spa

Pier House Resort & Spa

Pier House Resort & Spa
4.0 star property
Key West Historic District
9.0 out of 10, Wonderful, (1006)
"All accommodations were outstanding!"
United States
Bob
Pier House Resort & Spa
Outdoor pool, pool umbrellas, pool loungers
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton
4.0 star property
Old Town Key West
8.6 out of 10, Excellent, (1000)
"Great hotel, great beach, had a really good stay."
United States
Cristian Mihai
The price is Rp5.485.173
Rp7.176.719 total
includes taxes & fees
13 Jan - 14 Jan 2026
The Reach Key West, Curio Collection by Hilton
Front of property – evening/night
Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1025)
"Our stay was great!"
United States
Richard
The price is Rp7.024.535
Rp8.562.891 total
includes taxes & fees
4 Jan - 5 Jan 2026
Opal Key Resort & Marina, Key West
3 outdoor pools, pool umbrellas, pool loungers
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort
4.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (1005)
"Perfect location.. close to the wharf for the best dining experience."
United States
Marty
The price is Rp5.194.216
Rp6.899.687 total
includes taxes & fees
13 Jan - 14 Jan 2026
The Marker Key West Harbor Resort
Outdoor pool, pool loungers
Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort

Ocean Key Resort - A Noble House Resort
4.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (1004)
"Location, large rooms"
United States
george
The price is Rp8.717.129
Rp11.108.237 total
includes taxes & fees
12 Jan - 13 Jan 2026
Ocean Key Resort - A Noble House Resort
Outdoor pool, pool loungers
Havana Cabana at Key West

Havana Cabana at Key West

Havana Cabana at Key West
4.0 star property
New Town
8.8 out of 10, Excellent, (1706)
"Enjoyed stay, friendly staff and good shuttle bus"
United States
Abdul
Havana Cabana at Key West
Courtyard
Santa Maria Suites

Santa Maria Suites

Santa Maria Suites
4.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (1001)
"Awesome place we loved it"
United States
Josh
The price is Rp8.868.685
Rp11.108.908 total
includes taxes & fees
13 Jan - 14 Jan 2026
Santa Maria Suites
Mansion Room #201 - Ocean View with private balcony - Adults Only | Terrace/patio
Southernmost House

Southernmost House

Southernmost House
4.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (1000)
"Great place to stay. Staff was very friendly"
United States
Jacob
The price is Rp6.156.108
Rp8.481.623 total
includes taxes & fees
15 Jan - 16 Jan 2026
Southernmost House
Room 27C - Economy - Queen Bed - Adults Only 21+ | Egyptian cotton sheets, premium bedding, pillow-top beds, in-room safe
Bishop Hotel Key West

Bishop Hotel Key West

Bishop Hotel Key West
4.0 star property
Old Town Key West
9.8 out of 10, Exceptional, (338)
"Very clean rooms, great staff, excellent location. The breakfast each morning was great as was the Happy Hour at their bar."
United States
Jonathan
Bishop Hotel Key West
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Top Cow Key Hotel Reviews

Pier House Resort & Spa

Pier House Resort & Spa

10/10 Excellent
"All accommodations were outstanding!"
Bob 4-night trip
Posted 2 days ago
Pier House Resort & Spa
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

10/10 Excellent
"Room and staff were great! Staff came by each day to clean and reset the room. Bar and servers were helpful to get situated and watch some football"
Jason 4-night trip
Posted 3 days ago
Southernmost Beach Resort and Guesthouses

Frequently asked questions

What are the best 4-star hotels in Cow Key?
Relax in 4-star hotel comfort at The Perry Hotel & Marina Key West. Ranked highly by many of our guests, it offers windsurfing and designer toiletries. Also have a look at DoubleTree Resort by Hilton Grand Key - Key West. Premium bedding and windsurfing make this escape another leading pick in Cow Key.
How much does it cost to stay in a 4-star hotel in Cow Key?
To find a 4-star hotel in Cow Key that matches your budget, take advantage of Expedia's filter tool. Take a look at the availability during your travel dates and use our pricing filter to set your limit. You can also list your results by the most affordable property first.

  • Search for the lowest price from Rp5.077.280

What's the difference between 5-star and 4-star hotels in Cow Key?
If you decide to spend your holiday at a 4-star hotel in Cow Key, you'll typically find plenty of amenities to make sure you're relaxed, such as a pool, restaurant and gym. You can enjoy top-quality service and upmarket accommodation. Pick a 5-star hotel and you'll get a few more perks — think concierge assistance, on-site spas and indulgent turndown services. You'll most likely get extra amenities and first-rate services at a 5-star getaway, though both are superb options for luxury guests.