Sugarloaf Shores Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Holiday Package Deals in Sugarloaf Shores

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach

Cavalier Hotel South Beach

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Perfectly located on Ocean Drive with an old-school Art Deco vibe that feels both historic and fresh. The room was spotless, the A/C was ice cold, and the bed was genuinely comfortable. Staff was friendly and helpful. You’re across from the beach, but it still feels like a quiet escape. Would absolutely stay here again.

Reviewed on Jul. 1, 2025

The Retreat Collection at 1 Hotel & Homes South Beach

The Retreat Collection at 1 Hotel & Homes South Beach

5 out of 5
South Beach
per person
Sep 11 - Sep 16
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Miami (MIA)
8/10 Very Good! (1 review)
Pelican Grand Beach Resort - A Noble House Resort

Pelican Grand Beach Resort - A Noble House Resort

4 out of 5
East Fort Lauderdale
per person
Aug 11 - Aug 18
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.6/10 Excellent! (1,119 reviews)
Marcus the bell hop was above and beyond. He was INCREDIBLE and made our stay even better we couldn’t stop talking about his service.

Reviewed on Jul. 12, 2025

The Shelborne By Proper

The Shelborne By Proper

4 out of 5
South Beach
Save 100% on your flight
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
9.6/10 Exceptional! (4 reviews)
Wonderful hotel. Beautiful design and very attentive staff.

Reviewed on Jul. 7, 2025

President Hotel

President Hotel

3.5 out of 5
South Beach
Save 100% on your flight
per person
Aug 13 - Aug 20
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Miami (MIA)
8.4/10 Very Good! (1,596 reviews)
It was good, the one who attended us at check in was quite friendly and at breakfast anyway everything was good, very kind... I didn't like it was that we tried to get a glass of hot water and although it was only a "question" she replied "right now I'm very busy, come back in 10 minutes". On the day of cleaning, the one who was going to clean looked at me super badly "I knew that we can't be in the room when they go to do cleaning" but she was not nice at all and we were just about to leave the room...

Reviewed on Jul. 11, 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 Venture 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 CA $193 per night from Jul 20 to Jul 21
CA $193
CA $287 total
Jul 20 - Jul 21
includes taxes & fees
8.4/10 Very Good! (1,324 reviews)
"Absolutely wonderful place! The pool was so beautiful! We enjoyed the dining at both the pool bar and the restaurant. Highly recommend! We will be back!"

Reviewed on Jul. 12, 2025

Beachside Resort & Residences
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 CA $272 per night from Aug 11 to Aug 12
CA $272
CA $398 total
Aug 11 - Aug 12
includes taxes & fees
8.6/10 Excellent! (2,611 reviews)
"Love this property; property is bigger than I thought but had so much to offer; had fun activities if you wanted to be involved; a block from southern most point; everything is so close to stay"

Reviewed on Jul. 9, 2025

Southernmost Beach Resort and Guesthouses
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 CA $167 per night from Aug 11 to Aug 12
CA $167
CA $264 total
Aug 11 - Aug 12
includes taxes & fees
7.6/10 Good! (1,454 reviews)
"This resort was great. Staff was very helpful and accommodating. Irina at the bar was incredible! The shuttle service was perfect for an easy ride down to Duval. Would definitely stay here again!"

Reviewed on Jul. 11, 2025

Blue Flamingo Resort Key West
See all 3,494 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.

All Inclusive Vacations

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Frequently asked questions

How much does a Sugarloaf Shores vacation package cost?
From just CA $779, 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.