Find a Hotel in Cutthroat Harbor Estates

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Top hotels in Cutthroat Harbor Estates

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
7001 Shrimp Road Key West FL
Fully refundableReserve now, pay when you stay
$419 nightly
The price is $471 total per night from Jan 26 to Jan 27
$471 total
Jan 26 - Jan 27
Total with taxes and fees
A marina, 2 restaurants, and 2 outdoor pools are all featured at this smoke-free hotel. Traveling for business? Take advantage of the free WiFi in public areas, ...
The hotel was clean and quiet and all of the staff were friendly. The marina is great with a lot of different activities. We will definitely be returning to The Perry.

Reviewed on Jan 23, 2026

Opens in a new windowThe Perry Hotel & Marina Key West
Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

3.5 out of 5
3675 South Roosevelt Boulevard Key West FL
$487 nightly
The price is $548 total per night from Feb 23 to Feb 24
$548 total
Feb 23 - Feb 24
Total with taxes and fees
This hotel features an outdoor pool, a hot tub, and a restaurant. Guests will appreciate free perks like free self parking and WiFi in public areas. A snack ...
Great view, clean property. Beds were very comfortable. Having a telescope to view the stars is a nice touch

Reviewed on Jan 16, 2026

Opens in a new windowHyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Beach House, Key West

Hyatt Vacation Club at Beach House, Key West

3.5 out of 5
5051 Overseas Highway Key West FL
$503 nightly
The price is $566 total per night from Feb 25 to Feb 26
$566 total
Feb 25 - Feb 26
Total with taxes and fees
This hotel features an outdoor pool and a hot tub. Relax with a drink at the bar/lounge and enjoy perks like free self parking and free WiFi. A safe deposit ...
The room was amazing, the amenities were amazing, the property was amazing! the only issue worth noting is checking in. Our flight got in late and there was no staff at the front desk because they leave at 11. I had to call security which took extra time. Security guard was awesome and super nice ...

Reviewed on Jan 23, 2026

Opens in a new windowHyatt Vacation Club at Beach House, Key West
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$416 nightly
The price is $468 total per night from Jan 26 to Jan 27
$468 total
Jan 26 - Jan 27
Total with taxes and fees
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. ...
Had a wonderful view from our room. Shuttle is super convenient to Key West! Pools are very clean and live music was fantastic. Already booked for next year 😊

Reviewed on Jan 20, 2026

Opens in a new windowOceans Edge Key West Resort, Hotel & Marina
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$450 nightly
The price is $507 total per night from Feb 18 to Feb 19
$507 total
Feb 18 - Feb 19
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Business travelers can take advantage of the free WiFi in public areas. Enjoy the hot tub ...
Fun pool area! Rooms were clean, big, and unique.

Reviewed on Jan 19, 2026

Opens in a new windowHavana Cabana at Key West
Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$422 nightly
The price is $475 total per night from Jan 27 to Jan 28
$475 total
Jan 27 - Jan 28
Total with taxes and fees
This smoke-free hotel features a private beach, a marina, and 2 restaurants. Enjoy a day at the beach kayaking, or relax with sun loungers. Unwind with a drink ...
Nice

Reviewed on Jan 20, 2026

Opens in a new windowBeachside Resort & Residences
Just 20 miles from Key West!  Oceanfront, dockage, swimming pool

Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cudjoe Key FL
$600 nightly
The price is $666 total per night from Jan 26 to Jan 27
$666 total
Jan 26 - Jan 27
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
Great location. Quiet.

Reviewed on Jan 3, 2026

Opens in a new windowJust 20 miles from Key West! Oceanfront, dockage, swimming pool
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$418 nightly
The price is $470 total per night from Jan 26 to Jan 27
$470 total
Jan 26 - Jan 27
Total with taxes and fees
This hotel features 2 restaurants, 2 outdoor pools, and a 24-hour gym. There's fun for all ages with mini golf and an arcade/game room, and families will appreciate ...
First time staying here and would stay again! Came in to do 1/2 marathon, and have to stay, staff, shuttle, and the comfy room they sold me! Do you give repeat stay discounts?

Reviewed on Jan 20, 2026

Opens in a new windowBlue Flamingo Resort Key West
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
Fully refundableReserve now, pay when you stay
$443 nightly
The price is $498 total per night from Feb 1 to Feb 2
$498 total
Feb 1 - Feb 2
Total with taxes and fees
This resort features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public ...
Great Place

Reviewed on Jan 19, 2026

Opens in a new windowDoubleTree Resort by Hilton Grand Key - Key West
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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.

Cutthroat Harbor Estates Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Cutthroat Harbor Estates area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Cutthroat Harbor Estates to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Cutthroat Harbor Estates are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

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