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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
$407 nightly
The price is $458 total per night from Jul 27 to Jul 28
$458 total
Jul 27 - Jul 28
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 ...
"A little farther than I thought from Duvall st but still a really nice property"

Reviewed on Jun 30, 2026

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
$207 nightly
The price is $233 total per night from Jul 26 to Jul 27
$233 total
Jul 26 - Jul 27
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"

Reviewed on Jun 27, 2026

Opens in a new windowThe Perry Hotel & Marina 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
$182 nightly
The price is $204 total per night from Jul 16 to Jul 17
$204 total
Jul 16 - Jul 17
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 ...
"We had an amazing time, the staff was really nice. The pool was amazing. The only downside was we thought this was a 21 plus resort, but it’s not. We googled it, because it was a big selling point for us and it appeared to be, but there were a ton of kids there. Just something to be aware of if that’s ..."

Reviewed on Jun 28, 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
$206 nightly
The price is $232 total per night from Jul 12 to Jul 13
$232 total
Jul 12 - Jul 13
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 ...
"Great ocean view and convenient shuttle service to downtown. Pool is nice and parking is convenient. Get to the breakfast early to avoid the rush."

Reviewed on Jun 30, 2026

Opens in a new windowHampton Inn Key West FL
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
$286 nightly
The price is $322 total per night from Jul 22 to Jul 23
$322 total
Jul 22 - Jul 23
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 pool at the building we stayed in was disgusting. Floating bandaids, false eyelashes, cockroaches and debris was floating along with a film building up by the filters. Requested it to be cleaned and never was. Bathroom ceiling had black mold. Housekeeping came into our room without knocking at ..."

Reviewed on Jun 29, 2026

Opens in a new windowOceans Edge Key West Resort, Hotel & 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
$223 nightly
The price is $250 total per night from Jul 6 to Jul 7
$250 total
Jul 6 - Jul 7
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 ...
"We booked a two bedroom suite. It was not as advertised. There was a primary entry and then a secondary entry to two separate rooms. One room was small and was only a bedroom. The second room was an actual suite with a master bedroom. With three small kids this was less than ideal. I spoke to staff ..."

Reviewed on Jun 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
$184 nightly
The price is $207 total per night from Jul 5 to Jul 6
$207 total
Jul 5 - Jul 6
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 ...
"Did not like the rooms. They were like a motel set up"

Reviewed on Jul 1, 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
$169 nightly
The price is $190 total per night from Jul 15 to Jul 16
$190 total
Jul 15 - Jul 16
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 ...
"Overall if was decent but the hotel offering shuttles downtown in a van that could only seat 12 leaving others behind was not cool,especially considering we’re charged a resort fee. They have bigger buses but didn’t use them."

Reviewed on Jun 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
$145 nightly
The price is $163 total per night from Jul 7 to Jul 8
$163 total
Jul 7 - Jul 8
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 ...
"Staff was very friendly, location was excellent, and room was generous in size! Very happy with our stay here!"

Reviewed on Jun 30, 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.

Recent Cutthroat Harbor Estates hotel reviews by fellow wanderers

The Laureate Key West

The Laureate Key West

5 out of 5
Posted 2 hours ago
Travelocity Verified Review
"Our stay at the Laureate went very well! The suite we stayed in was clean and smelled good. Proper size for the four of us and never felt that we were on top of each other. One funny thing, I walked to Publix (about a 5-minute walk) to get some provisions. I came back with some frozen pizzas and then realized the unit does not have a stove. So I returned them for something else. The pool area was in good condition and we enjoyed the extra touches of bottled water, chilled towels, and table tennis. Front desk personnel were very prompt when we entered the lobby though had no other interaction with them. Would stay here again."
A verified traveler stayed at The Laureate Key West
The Laureate Key West

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