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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
$450 nightly
The price is $506 total per night from Mar 22 to Mar 23
$506 total
Mar 22 - Mar 23
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, ...
Nice room, food good but not great, a little expensive for food

Reviewed on Mar 2, 2026

Opens in a new windowThe Perry Hotel & Marina 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
$514 nightly
The price is $579 total per night from Mar 26 to Mar 27
$579 total
Mar 26 - Mar 27
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 WiFi. Self parking, concierge services, and ...
Stayed there for 5 nights and it was very pleasant!

Reviewed on Mar 2, 2026

Opens in a new windowHyatt Vacation Club at Beach House, 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
$463 nightly
The price is $521 total per night from Apr 1 to Apr 2
$521 total
Apr 1 - Apr 2
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 ...
The room was very clean beautiful our only problem was someone upstairs moving furniture across the floor until midnight??? The front desk staff was wonderful. Norma and Z were the best!

Reviewed on Mar 1, 2026

Opens in a new windowHyatt Vacation Club at Windward Pointe, 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
$381 nightly
The price is $429 total per night from Mar 4 to Mar 5
$429 total
Mar 4 - Mar 5
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. ...
The room was nice. We had a view of the marina, which was fun to watch the boats. All the pools seemed very nice. It was cold and rainy when we were there, but the property is nice and the shuttle bus to Key West is super convenient.

Reviewed on Mar 2, 2026

Opens in a new windowOceans Edge Key West Resort, Hotel & Marina
The Laureate Key West

The Laureate Key West

3.5 out of 5
3444 N Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$444 nightly
The price is $500 total per night from Mar 23 to Mar 24
$500 total
Mar 23 - Mar 24
Total with taxes and fees
This hotel features an outdoor pool and an indoor pool. If you want to take your pet along, this pet-friendly property offers everything you'll need for your ...
Room is excellent but no amenities and you need a car to get anywhere

Reviewed on Mar 2, 2026

Opens in a new windowThe Laureate Key West
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
$359 nightly
The price is $404 total per night from Mar 23 to Mar 24
$404 total
Mar 23 - Mar 24
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 ...
Great place to stay! Exceeded our expectations! Great food and bar. Clean and safe.

Reviewed on Mar 2, 2026

Opens in a new windowHavana Cabana at Key West
Just 20 miles from Key West!  Oceanfront, dockage, swimming pool

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

Cudjoe Key FL
This vacation home featured laundry facilities and barbecue grills.
This property is in great need of TLC as it was poorly maintained. Still unsure of the location of the pool. Floors were filthy, all of our feet were dirty and we only were there for less than a day. Okay for a one night stay, but would be very disappointed if the stay was longer. The host communicated ...

Reviewed on Feb 4, 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
$364 nightly
The price is $410 total per night from Mar 10 to Mar 11
$410 total
Mar 10 - Mar 11
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 ...
Breakfast was good, room was clean, stafff was excellent.

Reviewed on Mar 3, 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
$419 nightly
The price is $472 total per night from Mar 8 to Mar 9
$472 total
Mar 8 - Mar 9
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 ...
All of the above!!😀

Reviewed on Mar 2, 2026

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