Sugarloaf Shores Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
Sherry Frontenac Oceanfront Hotel

Sherry Frontenac Oceanfront Hotel

3 out of 5
North Beach
Price was S$1,427, price is now S$917 per person
S$917
per person
22 Dec - 28 Dec
found 9 hours ago
Return direct flight included
Philipsburg (SXM) to Miami (MIA)
6.8/10 (4,043 reviews)
Great

Reviewed on 31 Oct, 2026

Fontainebleau Miami Beach

Fontainebleau Miami Beach

4.5 out of 5
Mid Beach
Price was S$3,357, price is now S$2,138 per person
S$2,138
per person
22 Dec - 28 Dec
found 9 hours ago
Return direct flight included
Philipsburg (SXM) to Miami (MIA)
8.4/10 Very good! (9,147 reviews)
Excellence service, clean, smells fabulous and have been going there over 35 years and keep going back bc our family, with our children, who are now adults are going back with them and we love the hotel, although the prices of drinks by the pool are way too high, food is expensive but good, we always go back every year because we all love the Fontainbleau in Miami

Reviewed on 31 Oct, 2026

Mahalo Isles Apartments by Rocketstay

Mahalo Isles Apartments by Rocketstay

3 out of 5
East Fort Lauderdale
Price was S$2,932, price is now S$1,890 per person
S$1,890
per person
22 Dec - 28 Dec
found 9 hours ago
Return direct flight included
Philipsburg (SXM) to Miami (MIA)
10/10 Exceptional! (6 reviews)
Love it

Reviewed on 21 Sept, 2026

The Sunny Miami Sunny Isles Beach,Curio Collection by Hilton

The Sunny Miami Sunny Isles Beach,Curio Collection by Hilton

4 out of 5
Ocean Four
Price was S$3,091, price is now S$2,078 per person
S$2,078
per person
22 Dec - 28 Dec
found 9 hours ago
Return direct flight included
Philipsburg (SXM) to Miami (MIA)
9/10 Wonderful! (874 reviews)

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 Key and Venture Out Keys.

Find hotels in Cutthroat Harbor Estates

Top hotels in Sugarloaf Shores

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is S$410 per night from 1 Nov to 2 Nov
S$410
1 Nov - 2 Nov
includes taxes & fees
Margaritaville Beach House Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is S$288 per night from 19 Nov to 20 Nov
S$288
19 Nov - 20 Nov
includes taxes & fees
9/10 Wonderful! (1,896 reviews)
"Will stay again, felt like I was at a resort in the Jamaica"

Reviewed on 31 Oct, 2026

Havana Cabana at Key West
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 S$252 per night from 1 Nov to 2 Nov
S$252
1 Nov - 2 Nov
includes taxes & fees
8.6/10 Excellent! (2,766 reviews)
"Everything was perfect. They do charge 50.00 a day for parking and use of everything and 150 for incidentals. So make sure you plan ahead for those extra charges."

Reviewed on 31 Oct, 2026

Blue Flamingo Resort Key West
See all 3,446 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 S$917, 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.

Things to do

Private Sandbar Adventure in Key West Backcountry

Private Sandbar Adventure in Key West Backcountry

S$639
per traveller
Private Sandbar Adventure in Key West Backcountry
Guided Mangrove Eco Tours Kayak or Paddleboard Adventure

Guided Mangrove Eco Tours Kayak or Paddleboard Adventure

S$96
per adult
100% of travellers recommend
Guided Mangrove Eco Tours Kayak or Paddleboard Adventure
Private Luxury Sandbar Excursion

Private Luxury Sandbar Excursion in Key West

S$1,533
per traveller
Private Luxury Sandbar Excursion in Key West
See all activities in Summerland Key

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.