Sugarloaf Shores Vacation Packages

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Top Holiday Package Deals in Sugarloaf Shores

Price found within the past 48 hours. Click for updated prices.
The 27 Wynwood

The 27 Wynwood

4 out of 5
Wynwood Art District
Price was CA $2,446, price is now CA $1,495 per person
CA $1,495
per person
Jul 17 - Jul 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
10/10 Exceptional! (5 reviews)
Property is beautiful. The rooftop top pool is amazing. Everything is really close to the main street in wynwood. Will definitely be back.

Reviewed on Jun 5, 2026

Casablanca Miami Beach

Casablanca Miami Beach

3 out of 5
North Beach
Price was CA $3,869, price is now CA $2,037 per person
CA $2,037
per person
Jul 13 - Jul 20
found 3 hours ago
Roundtrip flight included
Montreal (YUL) to Miami (MIA)
5.8/10 (324 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.

Reviewed on Feb 22, 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 CA $20,471, price is now CA $10,879 per person
CA $10,879
per person
Aug 14 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Miami (MIA)
8/10 Very Good! (1 review)
Hotel Riu Plaza Miami Beach

Hotel Riu Plaza Miami Beach

4 out of 5
Mid Beach
Price was CA $3,328, price is now CA $1,988 per person
CA $1,988
per person
Aug 16 - Aug 23
found 21 hours ago
Roundtrip flight included
Hamilton (YHM) to Miami (MIA)
8/10 Very Good! (1,145 reviews)
The room was always super, super clean. All of the staff members were amazing, and always extremely kind&helpful. The beach view was beautiful, the breakfast was outstanding we were always excited to have breakfast, the buffet&food was delicious.

Reviewed on Jun 12, 2026

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort

4 out of 5
Price was CA $2,784, price is now CA $1,701 per person
CA $1,701
per person
Aug 2 - Aug 9
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9/10 Wonderful! (202 reviews)
Nice! I thoroughly enjoyed the experience. enjoyed it.

Reviewed on Jun 13, 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 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

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 $188 per night from Jun 15 to Jun 16
CA $188
CA $290 total
Jun 15 - Jun 16
includes taxes & fees
8.4/10 Very Good! (2,381 reviews)
"Todo excelente , muy buena atención , buena limpieza"

Reviewed on Jun 13, 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 refundableReserve now, pay when you stay
The price is CA $285 per night from Jul 6 to Jul 7
CA $285
CA $423 total
Jul 6 - Jul 7
includes taxes & fees
8.8/10 Excellent! (3,393 reviews)
"Staff members nice helpful and got checkin two hours early"

Reviewed on Jun 13, 2026

Southernmost Beach Resort and Guesthouses
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Jul 6 to Jul 7
CA $165
CA $225 total
Jul 6 - Jul 7
includes taxes & fees
8/10 Very Good! (1,237 reviews)
"easy check-in good vibe, efficient, clean enjoyed my stay… thank you. Enjoyed the pool. The hot tub wasn’t working so that was a bummer.. overall good experience"

Reviewed on Jun 12, 2026

Hilton Garden Inn Key West / The Keys Collection
See all 3,416 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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Frequently asked questions

How much does a Sugarloaf Shores vacation package cost?
From just CA $1,495, 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.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.