Cutthroat Harbor Estates Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Cutthroat Harbor Estates

Find the best Cutthroat Harbor Estates areas and neighborhoods for the activities you enjoy most. Learn more about Cutthroat Harbor Estates
Sugarloaf Shores featuring a bay or harbor

Sugarloaf Shores

While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.

Find hotels in Sugarloaf Shores

Cutthroat Harbor Estates Hotel Deals

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
The price is ₩526,104 per night from Feb 9 to Feb 10
₩526,104
₩682,614 total
Feb 9 - Feb 10
includes taxes & fees
8.8/10 Excellent! (1,790 reviews)
Very clean room. Amazing view. Wonderful property!! Would absolutely stay here again!!!

Reviewed on Jan 30, 2026

Oceans Edge Key West Resort, Hotel & Marina
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
The price is ₩533,782 per night from Feb 5 to Feb 6
₩533,782
₩682,073 total
Feb 5 - Feb 6
includes taxes & fees
8/10 Very Good! (1,910 reviews)
Staff was excellent! We enjoyed the pool and especially the complimentary shuttle downtown.

Reviewed on Feb 1, 2026

Blue 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
The price is ₩564,089 per night from Feb 5 to Feb 6
₩564,089
₩683,542 total
Feb 5 - Feb 6
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Flawless.

Reviewed on Feb 2, 2026

DoubleTree Resort by Hilton Grand Key - Key West
See all 1,399 properties in Cutthroat Harbor Estates
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.

Frequently asked questions

How much does a Cutthroat Harbor Estates vacation package cost?
From as low as . Yes, you read that right. Our Cutthroat Harbor Estates packages are an easy way to make your budget go further. Bundle your hotels, flights and car rentals and get to know this wonderful destination.
How do I get a cheap travel package to Cutthroat Harbor Estates?
Lock in flights that fit in with your schedule, add a hotel to your booking and watch the savings pile up with a Cutthroat Harbor Estates vacation package. It's as easy as that! From hotels and flights to tours and rental cars, Expedia makes traveling cheaply a cinch. And with over 550 airlines and 1,000,000 hotels throughout the world to select from, you won't be short of choice.
What are the top hotels in Cutthroat Harbor Estates?
Get your vacation off to a fantastic start by booking a stay at Oceanfront Home With Large Private Deck With Boat Dockage. It's one of most popular properties in Cutthroat Harbor Estates. Another option is Dazzling Bayfront Home With 2 Boat Docks.
How far in advance should I book my Cutthroat Harbor Estates vacation?
Browse Expedia to compare international flights as soon as you know your travel dates. You can usually purchase a seat up to 12 months before departure. If you don't see your preferred carrier, or you've left things to the last moment, don't despair. Cheap tickets to Cutthroat Harbor Estates sometimes emerge just weeks before the date of departure.
What does an Expedia Cutthroat Harbor Estates travel package include?
Expedia has all you need to organize your Cutthroat Harbor Estates trip, but how you structure your package is your choice. Pick from a combination of rental cars, flights and hotels. Searching for some tours or activities to keep you busy? Once you've made your booking, you can add them on too. Whatever your budget or style, there's a package deal to meet your needs.
What should I know before booking a Cutthroat Harbor Estates travel package?
Find deals that fit your budget with an Expedia package. Flights, hotels, rental cars — we have them all. You'll save big dollars just for combining your bookings. Whether you're taking off on a ski adventure or sipping cocktails on a beach, your dream vacation is only a few clicks away.
Can I choose my airline with a Cutthroat Harbor Estates Expedia vacation package?
Yes, the choice is yours. Expedia has access to more than 550 partner airlines around the world, so you can tailor your Cutthroat Harbor Estates adventure according to your needs and budget.
If I'm not able to travel, can I cancel my Cutthroat Harbor Estates vacation package?
Your situation can change in a flash, so yes, you can. You may be able to cancel or alter your Cutthroat Harbor Estates vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, hotel or airline may charge additional fees. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.