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Top hotels in Cutthroat Harbor Estates

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
$195 nightly
The price is $220 total per night from Aug 31 to Sep 1
$220 total
Aug 31 - Sep 1
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 ...
"Rooms were clean and well kept, the only complaint is the water in the shower took approximately 5 min to warm up. Had to turn water on and let it run. Pool was spacious and DJ played a variety of music. We would stay here again."

Reviewed on Aug 30, 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
$139 nightly
The price is $156 total per night from Aug 31 to Sep 1
$156 total
Aug 31 - Sep 1
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 ...
"My family and I enjoyed our stay! It was very clean complementary breakfast was yummy and the pool was beautiful! Definitely try the blackened mahi mahi sandwich!!"

Reviewed on Aug 30, 2026

Opens in a new windowHampton Inn Key West FL
Hilton Key West Resort & Marina

Hilton Key West Resort & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $188 total per night from Sep 7 to Sep 8
$188 total
Sep 7 - Sep 8
Total with taxes and fees
A marina, 6 outdoor pools, and a 24-hour gym are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas ...
"Excellent hotel; the room was extra clean."

Reviewed on Aug 30, 2026

Opens in a new windowHilton Key West Resort & Marina
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
$182 nightly
The price is $204 total per night from Aug 31 to Sep 1
$204 total
Aug 31 - Sep 1
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 ...
"It is a nice resort with a good view. Pool was nice with convenient service for drinks and food. The gym A/C was broken the whole week even with repeated complaints from many guests. 87 degrees was pretty hot to workout in. The rooms once inside were really quiet. Bed and pillows were comfy. Plenty ..."

Reviewed on Aug 30, 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
$166 nightly
The price is $187 total per night from Aug 31 to Sep 1
$187 total
Aug 31 - Sep 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 ...
"Clean, comfortable. Pools were excellent and a super nice and helpful staff."

Reviewed on Aug 30, 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
$144 nightly
The price is $162 total per night from Sep 7 to Sep 8
$162 total
Sep 7 - Sep 8
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 ...
"Check-in was easy, and the front desk staff were extremely kind and accommodating. We thought they were wonderful. Our only complaint was an unfortunate incident with another staff member. A middle-aged woman in a green shirt, wearing earbuds/headphones, was riding a motorized mobility scooter through ..."

Reviewed on Aug 30, 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
$135 nightly
The price is $152 total per night from Sep 22 to Sep 23
$152 total
Sep 22 - Sep 23
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 ...
"Priced perfect for what you get, clean rooms and friendly staff (mostly). Only down side was cost of on-site breakfast ($20.00), and $15 a day parking when they have one spot for each room reserved. Would definitely stay again."

Reviewed on Aug 30, 2026

Opens in a new windowHilton Garden Inn Key West / The Keys Collection
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 refundableReserve now, pay when you stay
$211 nightly
The price is $237 total per night from Sep 14 to Sep 15
$237 total
Sep 14 - Sep 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 ...
Opens in a new windowHyatt Vacation Club at Windward Pointe, Key West
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
$199 nightly
The price is $224 total per night from Sep 21 to Sep 22
$224 total
Sep 21 - Sep 22
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, ...
Opens in a new windowThe Perry Hotel & Marina 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.

Recent Cutthroat Harbor Estates hotel reviews by fellow wanderers

Beachside Resort & Residences

Beachside Resort & Residences

5 out of 5
Posted less than an hour ago
Travelocity Verified Review
"Room was clean, exactly what we had hoped for. Staff was friendly and helpful!"
A verified traveler stayed at Beachside Resort & Residences
Beachside Resort & Residences

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