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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
$434 nightly
The price is $488 total per night from Mar 5 to Mar 6
$488 total
Mar 5 - Mar 6
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, ...
Far from the great, maddening crowd of old town, but only a 20 minute, free shuttle ride away...a wonderful relaxing location with a great pool, bar and an additional full service restaurant and bar.

Reviewed on Feb 14, 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
Fully refundableReserve now, pay when you stay
$511 nightly
The price is $575 total per night from Mar 19 to Mar 20
$575 total
Mar 19 - Mar 20
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 ...
Loved the quiet relaxed atmosphere and the ability to cook or grill. Plenty of room to relax by the pool and loved the tiki bar situated nearby. Didn’t need the staff v often, but they were friendly and helpful when we did.

Reviewed on Feb 16, 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
$395 nightly
The price is $445 total per night from Mar 9 to Mar 10
$445 total
Mar 9 - Mar 10
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. ...
Excellent

Reviewed on Feb 17, 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
$404 nightly
The price is $455 total per night from Mar 1 to Mar 2
$455 total
Mar 1 - Mar 2
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 ...
Suite was spacious, well furnished, well decorated and very clean. Excellent ocean view, accommodating staff and adequate parking.

Reviewed on Feb 17, 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
$412 nightly
The price is $464 total per night from Mar 15 to Mar 16
$464 total
Mar 15 - Mar 16
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 ...
Fantastic vibes - I would definitely stay there again! Front desk staff was super friendly and helpful, the pool was beautiful, and breakfast was tasty. There were a few maintenance items in the room that need to be addressed, but the hotel seems to be refreshing all of the rooms so I imagine those ...

Reviewed on Feb 16, 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
$368 nightly
The price is $414 total per night from Mar 2 to Mar 3
$414 total
Mar 2 - Mar 3
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 ...
Be prepared for your “superior” room to have a view of an interior stucco hallway wall. Room was fairly nice but is a box with no view. Access to all rooms seemed to require a walk through a parking garage. The elevator was out in our assigned building. We later learned upon our ride back to the ...

Reviewed on Feb 16, 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
$629 nightly
The price is $698 total per night from Feb 22 to Feb 23
$698 total
Feb 22 - Feb 23
Total with taxes and fees
This vacation home featured laundry facilities and barbecue grills.
Everything was great!

Reviewed on Feb 2, 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
$436 nightly
The price is $491 total per night from Mar 1 to Mar 2
$491 total
Mar 1 - Mar 2
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 ...
Very responsive staff. Plenty of amenities including pools, activities, music, lawn games. A free shuttle to the historic district was great. The addition of a microwave in the room would be nice.

Reviewed on Feb 17, 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
$429 nightly
The price is $482 total per night from Mar 2 to Mar 3
$482 total
Mar 2 - Mar 3
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 ...
Good service great pool

Reviewed on Feb 17, 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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