Sugarloaf Shores Vacations from ￥144,459

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The Latest Sugarloaf Shores Vacation Packages

Price found within the past 48 hours. Click for updated prices.
President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
Price was ￥235,667, price is now ￥144,459 per person
￥144,459
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
First time in Miami and the President was nice, right in the middle of the action of South Beach! Dont expect this to a quiet quaint type hotel or location, lots of hustle and bustle! I liked it because was so close to the ocean and ocean drive and all the shops and restuarants. You dont need to rent a car if your gonna stay on south beach the entire time. Parking garage 2 blocks down 10 min walk is $20 a day

Reviewed on Jan 13, 2026

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
Price was ￥3,367,310, price is now ￥1,644,926 per person
￥1,644,926
per person
Apr 1 - Apr 5
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Miami (MIA)
8/10 Very Good! (1 review)
The Shelborne By Proper, a Member of Design Hotels

The Shelborne By Proper, a Member of Design Hotels

4 out of 5
South Beach
Save 100% on your flight
Price was ￥436,028, price is now ￥254,390 per person
￥254,390
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
9.4/10 Exceptional! (56 reviews)
The holding fee is ridiculously high

Reviewed on Jan 8, 2026

Bay Breeze Premium Apartments By Eskape Collection

Bay Breeze Premium Apartments By Eskape Collection

4 out of 5
Save 100% on your flight
Price was ￥243,531, price is now ￥158,084 per person
￥158,084
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
Our two bedroom apartment was very comfortable and quiet. We enjoyed our stay very much.

Reviewed on Dec 30, 2025

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 Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Upper Sugarloaf Key are some notable places to visit nearby.

Find hotels in Cutthroat Harbor Estates

Sugarloaf Shores Hotel Deals

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 ￥51,344 per night from Jan 19 to Jan 20
￥51,344
￥65,764 total
Jan 19 - Jan 20
includes taxes & fees
8.6/10 Excellent! (1,894 reviews)
Beautiful property, helpful staff , would highly recommend

Reviewed on Jan 11, 2026

Beachside 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
The price is ￥46,082 per night from Jan 15 to Jan 16
￥46,082
￥60,731 total
Jan 15 - Jan 16
includes taxes & fees
8/10 Very Good! (1,846 reviews)
Everything was clean, people were friendly. A lot to do there

Reviewed on Jan 11, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
The price is ￥73,956 per night from Jan 26 to Jan 27
￥73,956
￥94,843 total
Jan 26 - Jan 27
includes taxes & fees
8.6/10 Excellent! (3,008 reviews)
Room smelled musty all the time we were there and we ran the ac all the time. Also, breakfast was not served at guesthouse so we had to walk to main building every day. Not a big deal but it was not what we were told when we booked our stay. Otherwise, it was a very pleasant stay, all in all

Reviewed on Jan 12, 2026

Southernmost Beach Resort and Guesthouses
See all 3,540 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 vacation package cost?
From just ￥144,459, 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 1,000,000 properties throughout the world, which lets you customize your Sugarloaf Shores vacation.
Where should I stay in Sugarloaf Shores?
A vacation 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 vacation?
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 vacation packages today.
Can I choose my airline with a Sugarloaf Shores Expedia vacation package?
With a vacation 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 vacation 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.