Cutthroat Harbor Estates Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    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
Default Image

Sugarloaf Shores

Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Sugarloaf Beach and Upper Sugarloaf Sound.

Find hotels in Sugarloaf Shores

Top hotels in Cutthroat Harbor Estates

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 ฿4,160 per night from 12 Oct to 13 Oct
฿4,160
฿6,554 total
12 Oct - 13 Oct
includes taxes & fees
8.8/10 Excellent! (1,723 reviews)
"Great hotel"

Reviewed on 4 Oct 2025

Oceans Edge Key West Resort, Hotel & Marina
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 ฿3,872 per night from 15 Oct to 16 Oct
฿3,872
฿5,452 total
15 Oct - 16 Oct
includes taxes & fees
7.8/10 Good! (1,007 reviews)
"Super clean. The pool was amazing..friendly staff.."

Reviewed on 7 Oct 2025

DoubleTree 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
The price is ฿3,009 per night from 15 Oct to 16 Oct
฿3,009
฿4,299 total
15 Oct - 16 Oct
includes taxes & fees
7.8/10 Good! (1,098 reviews)
"I found it odd that I had to pay for parking at the hotel. Normally thats included. Would have been nice to know prior to booking."

Reviewed on 6 Oct 2025

Hilton Garden Inn Key West / The Keys Collection
See all 1,410 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 Harbour Estates holiday package cost?
From as low as . Yes, you read that right. Our Cutthroat Harbour 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 Harbour 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 Harbour Estates holiday package. It's as easy as that! From hotels and flights to tours and rental cars, Expedia makes travelling 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 Harbour Estates?
Get your holiday 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 Harbour Estates. Another option is Dazzling Bayfront Home With 2 Boat Docks.
How far in advance should I book my Cutthroat Harbour Estates holiday?
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 Harbour Estates sometimes emerge just weeks before the date of departure.
What does an Expedia Cutthroat Harbour Estates travel package include?
Expedia has all you need to organise your Cutthroat Harbour 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 Harbour 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 holiday is only a few clicks away.
Can I choose my airline with a Cutthroat Harbour Estates Expedia holiday package?
Yes, the choice is yours. Expedia has access to more than 550 partner airlines around the world, so you can tailor your Cutthroat Harbour Estates adventure according to your needs and budget.
If I'm not able to travel, can I cancel my Cutthroat Harbour Estates holiday package?
Your situation can change in a flash, so yes, you can. You may be able to cancel or alter your Cutthroat Harbour Estates holiday 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.