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
per person
19 May - 24 May
found 17 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8/10 Very Good! (1,143 reviews)
Great place to stay. You have your very one loft, But, Unfortunately it rained in the outdoor furnitures

Reviewed on 31 Mar 2025

Henrosa Hotel

Henrosa Hotel

3.5 out of 5
South Beach
per person
19 May - 24 May
found 17 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8.4/10 Very Good! (768 reviews)
The Hotel decoration with a residential feeling making you feel at home, encompassing all details. Very unique. Rooms spacious, clean, decorated with detail. Stafff five star. Location close to nightlife, restaurants, steps away a beautiful beach, Loved it!!! Will return.

Reviewed on 19 Mar 2025

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
per person
19 May - 24 May
found 17 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8/10 Very Good! (5,944 reviews)
Top 3 best hotel/resort experiences EVER. By far me and my daughter’s favorite vacation each year and we plan on returning at least once a year but would love to visit as much as possible. Not one thing I can complain about or nitpick. Hands down FANTASTIC all around.

Reviewed on 2 Apr 2025

Sunrise in Miami Suites

Sunrise in Miami Suites

2 out of 5
South Beach
per person
19 May - 24 May
found 17 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
10/10 Exceptional! (1 review)
Wow! Our stay here truly exceeded my expectations! The experience was by far the smoothest! As Someone who is new to the virtual desk, communications were efficient. The location was so spacious and welcoming and a perfect walk to the beach! Such an accommodating host! Thank you for a great stay!

Reviewed on 4 Mar 2025

President Villa

President Villa

3.5 out of 5
South Beach
per person
19 May - 24 May
found 17 hours ago
Return flight included
Newark Liberty Intl. Airport (EWR) to Miami (MIA)
8.2/10 Very Good! (1,002 reviews)
All fine, staff friendly.

Reviewed on 30 Mar 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 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
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is €520 per night from 8 Apr to 9 Apr
€520
includes taxes & fees
8 Apr - 9 Apr
8.6/10 Excellent! (2,368 reviews)
"Less than luxurious for the price. Handy for Duval. A high end motel that does everything “ok”."

Reviewed on 30 Mar 2025

Southernmost Beach Resort
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 €275 per night from 22 Apr to 23 Apr
€275
includes taxes & fees
22 Apr - 23 Apr
8.2/10 Very Good! (1,016 reviews)
"Great place to stay! It has the best of both worlds, right at the ocean and a nice pool!"

Reviewed on 31 Mar 2025

Beachside Resort & Residences
Fairfield Inn and Suites by Marriott Key West
Fairfield Inn and Suites by Marriott Key West
3 out of 5
2400 N Roosevelt Blvd, Key West, FL
The price is €255 per night from 28 Apr to 29 Apr
€255
includes taxes & fees
28 Apr - 29 Apr
7.8/10 Good! (1,097 reviews)
Fairfield Key West
"The hotel front desk staff was very helpful and friendly. The rooms were nice, although we did have an A/C issuue but tahe staff adjusted our bill for it. The free breakfast was good, and the staff kept it stocked with both hot and cold choices. The pool area was beautiful and relaxing, with a pool ..."

Reviewed on 25 Mar 2025

Fairfield Inn and Suites by Marriott Key West
See all 3,504 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 €443, 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.