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.
Avi Lux Stay

Avi Lux Stay

4.5 out of 5
East Fort Lauderdale
Price was CA $2,354, price is now CA $1,142 per person
CA $1,142
per person
Dec 20 - Dec 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
7.6/10 Good! (10 reviews)
If you are looking for a quiet place to stay this suite is NOT recommended. You can hear motorcycles and racing cars at all hours of the night. Valet is $60 per night mandatory payment required upon check in for the entire length of your stay tips not included. This is not stated in the description prior to booking. BEWARE.

Reviewed on Aug 28, 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
Price was CA $29,885, price is now CA $15,721 per person
CA $15,721
per person
Jan 15 - Jan 19
found 7 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Miami (MIA)
8/10 Very good! (1 review)
Horrible checkin / checkout... Would never stay there again...Double charged me entire stay and still fighting to get someone to refund 2nd one that is so clearly a duplicate for same stay....

Reviewed on Jun 22, 2016

YotelPad Miami

YotelPad Miami

4 out of 5
Downtown Miami
Price was CA $2,388, price is now CA $1,263 per person
CA $1,263
per person
Jan 24 - Jan 29
found 13 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
8.4/10 Very good! (543 reviews)

Miami Vacation Rentals Downtown with Pool

Miami Vacation Rentals Downtown with Pool

2.5 out of 5
Downtown Miami
Save 100% on your flight
Price was CA $2,758, price is now CA $1,563 per person
CA $1,563
per person
Jan 24 - Jan 29
found 2 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
No reviews

Miami Vacation Rentals - Brickell

Miami Vacation Rentals - Brickell

4 out of 5
Brickell
Save 100% on your flight
Price was CA $5,604, price is now CA $3,220 per person
CA $3,220
per person
Dec 26 - Jan 1
found 13 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Miami (MIA)
8.8/10 Excellent! (578 reviews)
El apartamento es muy lindo, muy amplio, muy cómodo, con una vista divina y excelentemente bien ubicado. Las camas, y almohadas súper cómodas. El apartamento muy limpio y sus sábanas y toallas también muy limpias. Solo recomiendo que los anfitriones deben estar más atentos a los detalles del apartamento; el black out del segundo cuarto nunca sirvió y entra el sol directo toda la mañana, los keys/fobs nunca sirvieron, siempre tocaba ir a security a que los activaran, la cafetera votaba el agua por debajo y los sartenes de la cocina ya creo q hay q cambiarlos. Pero en general muy bueno y cómodo el apartamento!

Reviewed on Oct 18, 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
A calm lake with several white birds, including herons and pelicans, on the water's edge.

Cutthroat Harbor Estates

While Cutthroat Harbor Estates isn't home to many top sights, Venture Key and Venture Out Keys are some notable places to visit nearby.

Find hotels in Cutthroat Harbor Estates

Sugarloaf Shores Hotel Deals

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 CA $325 per night from Nov 18 to Nov 19
CA $325
CA $455 total
Nov 18 - Nov 19
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 CA $182 per night from Nov 30 to Dec 1
CA $182
CA $295 total
Nov 30 - Dec 1
includes taxes & fees
9/10 Wonderful! (1,902 reviews)
"The shuttle service is extremely helpful if you don’t have a car given it is quietly away from the heavy tourist area. The pool was wonderful with an array of floats. Nice temperature! Bar service and breakfast were great. Staff was very nice and informative about places to go and eat. They could ..."

Reviewed on Nov 11, 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 CA $165 per night from Nov 17 to Nov 18
CA $165
CA $265 total
Nov 17 - Nov 18
includes taxes & fees
8.6/10 Excellent! (2,788 reviews)
"Nice pool area & amenities.Helpful staff. Room could use a microwave & table(or desk)."

Reviewed on Nov 11, 2026

Blue Flamingo Resort Key West
See all 3,422 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
Family Vacations

Frequently asked questions

How much does a Sugarloaf Shores vacation package cost?
From just CA $1,142, 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.

Things to do

Discover US East Coast Self Guided Audio Tour

Discover US East Coast Self Guided Audio Tour

CA $205
per traveller
Discover US East Coast Self Guided Audio Tour
Private Sandbar Adventure in Key West Backcountry

Private Sandbar Adventure in Key West Backcountry

CA $707
per traveller
Private Sandbar Adventure in Key West Backcountry
Private Luxury Sandbar Excursion

Private Luxury Sandbar Excursion in Key West

CA $1,697
per traveller
Private Luxury Sandbar Excursion in Key West
See all activities in Summerland Key

Explore a world of travel with Expedia

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