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
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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

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 2.514.935 ₫ per night from 30 Nov to 1 Dec
2.514.935 ₫
4.312.164 ₫ total
30 Nov - 1 Dec
includes taxes & fees
7.8/10 Good! (1,709 reviews)
The property was great, but the front desk did not communicate properly regarding the credits or benefits. Also, there is always a rush so they need more staffs to assist.

Reviewed on 20 Nov 2025

Blue Flamingo Resort 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 2.298.766 ₫ per night from 1 Dec to 2 Dec
2.298.766 ₫
3.327.675 ₫ total
1 Dec - 2 Dec
includes taxes & fees
7.8/10 Good! (1,132 reviews)
Great pool and exercise/weight room area!

Reviewed on 23 Nov 2025

Hilton Garden Inn Key West / The Keys Collection
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 3.934.528 ₫ per night from 1 Dec to 2 Dec
3.934.528 ₫
6.012.809 ₫ total
1 Dec - 2 Dec
includes taxes & fees
8.8/10 Excellent! (1,739 reviews)
We thoroughly enjoyed our stay at Oceans Edge. It was a beautiful relaxing oasis for us to spend a few days. The weather was not great (windy & a little chilly) so we couldn't use the paddleboards or kayaks. The food at the restaurant was delicious and we ended up eating there for almost all our ...

Reviewed on 18 Nov 2025

Oceans Edge Key West Resort, Hotel & Marina
See all 3,530 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.