Sugarloaf Shores Holidays

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

The Penguin Hotel

3.5 out of 5
South Beach
Price was €593, price is now €338 per person
€338
per person
5 May - 9 May
found 1 day ago
Return flight included
New York (JFK) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
Clean, staff were very nice. Location was great.

Reviewed on 27 Feb 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 €12,981, price is now €6,407 per person
€6,407
per person
5 May - 9 May
found 1 day ago
Return flight included
New York (JFK) to Miami (MIA)
8/10 Very Good! (1 review)
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Price was €733, price is now €390 per person
€390
per person
5 May - 9 May
found 1 day ago
Return flight included
New York (JFK) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
Loved the location, room was nice, bathroom very small, very friendly staff, slow service at restaurant in the morning. Will go back

Reviewed on 24 Feb 2026

President Hotel

President Hotel

3.5 out of 5
South Beach
Price was €753, price is now €411 per person
€411
per person
5 May - 9 May
found 1 day ago
Return flight included
New York (JFK) to Miami (MIA)
8.4/10 Very Good! (1,775 reviews)
Location is great, the rest is average or below average

Reviewed on 26 Feb 2026

President Hotel Villa

President Hotel Villa

3.5 out of 5
South Beach
Price was €753, price is now €411 per person
€411
per person
5 May - 9 May
found 1 day ago
Return flight included
New York (JFK) to Miami (MIA)
8.2/10 Very Good! (997 reviews)
nice location, good room. nice breakfast and evening reception

Reviewed on 22 Feb 2026

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
Bird refuge wildlife background panorama banner of nature landscape ocean birds in Key West, Florida. Animals of the USA.

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 Key and Venture Out Keys.

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 refundable
The price is €464 per night from 30 Mar to 31 Mar
€464
30 Mar - 31 Mar
includes taxes & fees
8.8/10 Excellent! (3,095 reviews)
Room lighting was not working properly. In room phone didn’t work. Very little hot water in shower.

Reviewed on 26 Feb 2026

Southernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is €318 per night from 2 Mar to 3 Mar
€318
2 Mar - 3 Mar
includes taxes & fees
8/10 Very Good! (2,107 reviews)
Reception was friendly, efficient, rooms were clean our second visit to Ibis- Key West

Reviewed on 25 Feb 2026

Ibis Bay Beach Resort
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 €381 per night from 10 Mar to 11 Mar
€381
10 Mar - 11 Mar
includes taxes & fees
8.2/10 Very Good! (1,955 reviews)
We always stay at Blue Flamingo when we are in Key West. You should, too. Friendly, helpful team, great amenities, and a Starbucks in the hotel! What more could one want?

Reviewed on 27 Feb 2026

Blue Flamingo Resort Key West
See all 3,466 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 €338, 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 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.