Sugarloaf Shores Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Sugarloaf Shores

Find the best Sugarloaf Shores areas and neighborhoods for the activities you enjoy most. Learn more about Sugarloaf Shores
A calm lake with several white birds, including herons and pelicans, on the water's edge.

Cutthroat Harbor Estates

While there might not be top attractions in Cutthroat Harbor Estates, you can explore the larger area and discover places like Venture Out Keys and Upper Sugarloaf Key.

Find hotels in Cutthroat Harbor Estates

Top hotels in Sugarloaf Shores

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is 4.591.178 ₫ per night from 4 Aug to 5 Aug
4.591.178 ₫
7.089.491 ₫ total
4 Aug - 5 Aug
includes taxes & fees
8.8/10 Excellent! (3,464 reviews)
"Our room was very clean and all the staff was very friendly and helpful. We enjoyed our stay very much and will definitely go back!"

Reviewed on 23 Jul 2026

Southernmost Beach Resort and Guesthouses
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
The price is 3.076.487 ₫ per night from 17 Aug to 18 Aug
3.076.487 ₫
5.977.453 ₫ total
17 Aug - 18 Aug
includes taxes & fees
8.6/10 Excellent! (2,363 reviews)
"Nice place wil book again"

Reviewed on 23 Jul 2026

Beachside Resort & Residences
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 3.540.946 ₫ per night from 18 Aug to 19 Aug
3.540.946 ₫
4.723.805 ₫ total
18 Aug - 19 Aug
includes taxes & fees
Hilton Garden Inn Key West / The Keys Collection
See all 3,433 properties in Sugarloaf Shores
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 Sugarloaf Shores holiday package cost?
From just , you can tailor your Sugarloaf Shores package the way you want. Simply bundle hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Sugarloaf Shores?
One of the simplest ways to save money (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we've got them all covered. Select the combination that best suits you and watch your savings pile up. We know a travel package is never one-size-fits-all. That's why Expedia offers over 550 air carriers and 1null000null000 properties throughout the world, which lets you customize your Sugarloaf Shores holiday.
Where should I stay in Sugarloaf Shores?
A holiday in Sugarloaf Shores isn't complete without seeing Sugarloaf Beach, Upper Sugarloaf Sound and Upper Sugarloaf Key. Spend your evenings close to these popular attractions and make sightseeing simple.
What are the top hotels in Sugarloaf Shores?
South Point Sunset - Florida Keys Waterfront 3 and Paradise Point - Amazing Views are among the most well-known properties in Sugarloaf Shores. Why not look up the rates and amenities at each and then decide?
How far in advance should I book my Sugarloaf Shores holiday?
While not all airlines advertise tickets early, you can usually start comparing international flights on Expedia up to 12 months in advance. This is the time when you'll score some incredible bargains. If you've left things to the last minute, you might get lucky. Discounted prices occasionally appear just weeks prior to departure.
What does an Expedia Sugarloaf Shores travel package include?
That mostly depends on you. You can pick from a variety of Sugarloaf Shores packages, such as a rental car, flight and hotel. You can also book a flight and a hotel, or a flight with a rental car. Once you've made your booking, you can add on the fun stuff like tours and activities. Whatever your perfect Sugarloaf Shores break looks like, you'll save!
What should I know before booking a Sugarloaf Shores travel package?
You'll score great savings when you combine your hotels, flights and rental cars into a package. Not only that, booking everything in one spot will make your trip planning easier. So why waste time or money? Whether you're putting together a fancy romantic getaway or a budget solo adventure, take a look at our holiday packages today.
Can I choose my airline with a Sugarloaf Shores Expedia holiday package?
With a holiday package, the choice is in your hands. Whether you're looking to fly to Sugarloaf Shores in business or coach, simply select from the available airline options. Expedia has access to more than 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Sugarloaf Shores holiday package?
Yes, it's possible to cancel your Sugarloaf Shores booking if your travel plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal for more information.