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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
$346 nightly
The price is $389 total per night from Apr 19 to Apr 20
$389 total
Apr 19 - Apr 20
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, ...
great variety on the menus. we enjoyed our stay. My only negative comment is related to the loud conversations of our neighbors on the balcony two days and also a couple were sitting by the fire pits while they were on a phone call that they put on speaker. These incidents made our time relaxing ...

Reviewed on Mar 28, 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
$419 nightly
The price is $471 total per night from Apr 23 to Apr 24
$471 total
Apr 23 - Apr 24
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 ...
Everything was awesome.

Reviewed on Apr 1, 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
$456 nightly
The price is $513 total per night from Apr 20 to Apr 21
$513 total
Apr 20 - Apr 21
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 ...
Room was very spacious and clean!

Reviewed on Mar 30, 2026

Opens in a new windowHyatt Vacation Club at Windward Pointe, Key West
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
$250 nightly
The price is $281 total per night from Apr 20 to Apr 21
$281 total
Apr 20 - Apr 21
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 ...
Yes,yes

Reviewed on Apr 1, 2026

Opens in a new windowThe Laureate 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
$278 nightly
The price is $313 total per night from Apr 29 to Apr 30
$313 total
Apr 29 - Apr 30
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. ...
Amazing location, the room and property were spotless. Staff were very friendly. Would stay here again!

Reviewed on Apr 2, 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
$287 nightly
The price is $323 total per night from May 3 to May 4
$323 total
May 3 - May 4
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 ...
This hotel was advertised as adult only and there were kids everywhere. Was very frustrating since we were looking to get a vacation with no screaming kids.

Reviewed on Apr 1, 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
$326 nightly
The price is $367 total per night from Apr 5 to Apr 6
$367 total
Apr 5 - Apr 6
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 ...
The private beach is not what was expected, but adequate for children to play.

Reviewed on Apr 1, 2026

Opens in a new windowBeachside Resort & Residences
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
$308 nightly
The price is $347 total per night from May 3 to May 4
$347 total
May 3 - May 4
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 ...
We loved our stay here, absolutely loved it!!! Beautiful property, great pool temp and atmosphere, good food and drinks on site and most of the staff was super friendly and over the top accommodating, we will be back!!! Thank you Blue Flamingo

Reviewed on Apr 2, 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
$275 nightly
The price is $310 total per night from Apr 19 to Apr 20
$310 total
Apr 19 - Apr 20
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 ...
Yes

Reviewed on Mar 31, 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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