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Top hotels in Cutthroat Harbor Estates

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
Fully refundable
$345 nightly
The price is $388 total per night from Jun 14 to Jun 15
$388 total
Jun 14 - Jun 15
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 and balcony were fantastic. The pool, grounds, and view of the ocean were lovely. The staff was super welcoming and friendly when we arrived. We enjoyed the close restaurant and walking path right across the street."

Reviewed on May 28, 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
$184 nightly
The price is $207 total per night from Jun 2 to Jun 3
$207 total
Jun 2 - Jun 3
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 ...
"Parking garage, clean and kitchen very nice too, everything in the room was convenient , coffee maker, toaster, etc"

Reviewed on May 31, 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
$201 nightly
The price is $226 total per night from Jun 24 to Jun 25
$226 total
Jun 24 - Jun 25
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 property was a gem. We loved the pool and DJ. The whole place is a great vibe."

Reviewed on May 31, 2026

Opens in a new windowHavana Cabana at Key West
Hampton Inn Key West FL

Hampton Inn Key West FL

2.5 out of 5
3755 S Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $201 total per night from Jun 7 to Jun 8
$201 total
Jun 7 - Jun 8
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 24-hour ...
"Clean room with great ocean view! Great breakfast with great daily variety! Great gym! Great pool with poolside shack bar and grill! Staff were great, helpful with any questions and very friendly! Van service to airport and downtown on time and great drivers! We will be back!!! 5 stars!"

Reviewed on May 31, 2026

Opens in a new windowHampton Inn Key West FL
Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

3.5 out of 5
3852 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $179 total per night from Jun 7 to Jun 8
$179 total
Jun 7 - Jun 8
Total with taxes and fees
This hotel features a bar/lounge, a poolside bar, and an outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in ...
"Dont think that it was far from old town. Its a nice place to vacate at."

Reviewed on May 27, 2026

Opens in a new windowFairfield by Marriott Inn & Suites Key West at The Keys Collection
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
$212 nightly
The price is $239 total per night from Jun 2 to Jun 3
$239 total
Jun 2 - Jun 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 ...
"Great"

Reviewed on May 31, 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
$187 nightly
The price is $210 total per night from Jun 30 to Jul 1
$210 total
Jun 30 - Jul 1
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 a playground, and families will appreciate ...
"Very disappointing, read why. If a hot tub/real restaurants are important/necessary to you, do not book here. They claim there is a hot tub on the premises, it is actually a 7 minute walk to a completely different hotel. (The properties are owned by the same company,this is false advertising. When ..."

Reviewed on May 31, 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
$177 nightly
The price is $199 total per night from Jun 28 to Jun 29
$199 total
Jun 28 - Jun 29
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 ...
"S"

Reviewed on May 29, 2026

Opens in a new windowDoubleTree Resort by Hilton Grand Key - Key West
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
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $167 total per night from Jun 29 to Jun 30
$167 total
Jun 29 - Jun 30
Total with taxes and fees
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the business center and free WiFi in public ...
"Not the best location but you get what you pay for. Shuttle was good."

Reviewed on Jun 1, 2026

Opens in a new windowHilton Garden Inn Key West / The Keys Collection
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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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