Book 5 Star Hotels in Cow Key

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Jan 3 - Jan 4
Tonight
Check prices in Cow Key for tonight, Jan 3 - Jan 4
Jan 4 - Jan 5
Tomorrow night
Check prices in Cow Key for tomorrow night, Jan 4 - Jan 5

Featured Cow Key 5 Stars Hotels

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road Key West FL
Free Cancellation
Reserve now, pay when you stay
0.37 mi from city center
$378 nightly
The price is $425 total per night
$425 total
Jan 20 - Jan 21
Total with taxes and fees
Guests of The Perry Hotel & Marina Key West have access to a marina, 2 outdoor pools, and a 24-hour gym. If you drive, self parking is USD 30.38 per night, and there's also an area shuttle. The front desk has multilingual staff on hand 24/7 to help with luggage storage, securing valuables, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls and an off-leash area. Additional amenities include free WiFi in public areas, conference space, and a microwave in a common area.
Pool
Pet friendly
DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West

4 out of 5
3990 S Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
0.58 mi from city center
$289 nightly
The price is $325 total per night
$325 total
Jan 4 - Jan 5
Total with taxes and fees
Guests staying at DoubleTree Resort by Hilton Grand Key - Key West enjoy an outdoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, self parking is USD 20 per night, or you can take advantage of the free airport shuttle (available on request). Multilingual staff at the front desk are standing by 24/7 to help with tours or tickets, luggage storage, and dry cleaning/laundry. Additional amenities include meeting rooms, a conference center, and a 24-hour business center.
Pool
Free airport shuttle
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Free Cancellation
Reserve now, pay when you stay
0.81 mi from city center
$273 nightly
The price is $307 total per night
$307 total
Jan 11 - Jan 12
Total with taxes and fees
Guests of Oceans Edge Key West Resort, Hotel & Marina have access to a marina, 6 outdoor pools, and a 24-hour gym. If you drive, self parking is USD 32.63 per night, and there's also an area shuttle. Multilingual staff at the front desk are standing by 24/7 to help with tours or tickets, luggage storage, and securing valuables. Other amenities at this luxury hotel include free WiFi in public areas, meeting rooms, and free use of bicycles.
Pool
Pet friendly
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
1.01 mi from city center
$282 nightly
The price is $317 total per night
$317 total
Jan 8 - Jan 9
Total with taxes and fees
Guests staying at Hilton Garden Inn Key West / The Keys Collection enjoy an outdoor pool, a gym, and free WiFi in public areas. If you drive, self parking is USD 15 per day, and there's also a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with concierge services, luggage storage, and dry cleaning/laundry. Additional amenities include a hot tub, meeting rooms, and a business center.
Pool
Hot Tub
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Free Cancellation
Reserve now, pay when you stay
1.01 mi from city center
$322 nightly
The price is $363 total per night
$363 total
Jan 19 - Jan 20
Total with taxes and fees
Guests of Beachside Resort & Residences have access to a private beach, a marina, and an outdoor pool. If you drive, self parking is USD 25.00 per night, and there's also a free area shuttle. The front desk has multilingual staff on hand 24/7 to help with dry cleaning/laundry, concierge services, and luggage storage. Other amenities at this beach hotel include a 24-hour gym, free WiFi in public areas, and a hot tub.
On private beach
Pool
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
1.16 mi from city center
$292 nightly
The price is $329 total per night
$329 total
Jan 4 - Jan 5
Total with taxes and fees
Blue Flamingo Resort Key West features 2 outdoor pools, karaoke, and a 24-hour gym. If you drive, self parking is USD 15.00 per night, and there's also a free area shuttle. The 24-hour front desk has multilingual staff ready to assist with tours/tickets and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Other amenities at this family-friendly hotel include free WiFi in public areas, a hot tub, and meeting rooms.
Pool
Hot Tub
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
1.5 mi from city center
$293 nightly
The price is $329 total per night
$329 total
Jan 5 - Jan 6
Total with taxes and fees
At Havana Cabana at Key West , guests have access to an outdoor pool, free WiFi in public areas, and a hot tub. A stay here includes free parking. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, securing valuables, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a meeting room, a terrace, and an ATM.
Pool
Hot Tub
Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Boulevard Key West FL
Free Cancellation
Reserve now, pay when you stay
2.03 mi from city center
$345 nightly
The price is $389 total per night
$389 total
Jan 7 - Jan 8
Total with taxes and fees
Margaritaville Beach House Key West features an outdoor pool, a 24-hour gym, and a business center. The front desk is staffed 24/7 to help with tours or tickets, luggage storage, and dry cleaning/laundry. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this beach hotel include a banquet hall and an ATM.
Pool
Pet friendly
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Free Cancellation
3.6 mi from city center
$419 nightly
The price is $472 total per night
$472 total
Jan 26 - Jan 27
Total with taxes and fees
Guests of Southernmost Beach Resort and Guesthouses have access to a full-service spa, 3 outdoor pools, and a gym. Self parking is offered for USD 53.75 per day. Multilingual staff at the 24-hour front desk can assist with dry cleaning/laundry, tours or tickets, and luggage storage. Other amenities at this beach hotel include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Spa
Don't see what you're looking for?
See all available properties in Cow Key
View all properties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Best 5 star hotels in Cow Key

Guarantee yourself a relaxing time when you book the best of the best: 5 star hotels in Cow Key. After all, treating yourself to the finer things is what vacations are about. 

What are the criteria for a 5 star hotel?
5 star hotel requirements include distinctive services and amenities that surpass all others. These Cow Key hotels bring an incomparable degree of quality and attention to detail, with guest satisfaction being top priority. Your 5 star hotel should be dressed to impress, with design details like marble surfaces and hi-tech fixtures.

What amenities can I expect at a 5 star hotel?
Cow Key 5 star hotels and resorts typically offer luxury amenities such as:

  • Gourmet restaurant
  • Full-service fitness center with pool
  • Luxury spa 
  • Welcome gifts upon arrival
  • Top-of-the-line beds and linens 
  • Designer personal care products
  • Premium cable, free Wi-Fi and device docking stations

How do I find an amazing 5 star hotel?
Finding 5 star hotel deals in Cow Key with Orbitz is as easy as your stay will be. For the top-shelf vacation you deserve, we’ll help you choose the right hotel in the right place: 

  • Search hotels by price, ranging from $307 to $472
  • Find the best-loved hotels through word-of-mouth advice when you check out over reviews by Orbitz travelers
  • Choose from 3,208 5 star hotels in Cow Key!

Cow Key hotels essential information

Accommodation
3,208 hotels
Lowest Price
$307
Highest Price
$472
Popular hotels
Beachside Resort & Residences, Blue Flamingo Resort Key West, Oceans Edge Key West Resort, Hotel & Marina, Southernmost Beach Resort and Guesthouses, DoubleTree Resort by Hilton Grand Key - Key West, Hilton Garden Inn Key West / The Keys Collection, Margaritaville Beach House Key West, The Perry Hotel & Marina Key West, Havana Cabana at Key West

Recent Reviews

Beachside Resort & Residences

Beachside Resort & Residences

5/5 Excellent
"Overall a great experience. Staff is amazing and so friendly. You get prompt service . They keep the pool and whirlpool very clean and quite warm for a December winter. The large rooms and well equipped kitchen are a big plus. "
A verified traveler stayed at Beachside Resort & Residences
Posted 3 days ago
Beachside Resort & Residences

More to Explore