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 Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $18,011
per person
Nov 7 - Nov 14
found 1 day 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
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
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.
Cudjoe Gardens
When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.
Breezeswept Beach Estates
While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Coupon Bight Aquatic Preserve are some notable places to visit nearby.
Sugarloaf Shores Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
CA $242
CA $374 total
Sep 27 - Sep 28
includes taxes & fees
8.6/10 Excellent! (3,595 reviews)
"My husband and I were a bit disappointed with this property. Upon arrival were were charged unexpected "fees" and $50 per day to park the car. The TV was not working properly and we experienced an ant invasion overnight. Really expensive for what we got. We would not stay here again."
Reviewed on Sep 14, 2026
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
CA $152
CA $249 total
Sep 15 - Sep 16
includes taxes & fees
8.6/10 Excellent! (2,673 reviews)
"I really liked the hotel, polite staff. But they are confusing. We went through a lot of stress. At all times at the reception. We found the unprepared team. We were in a group of friends 18 people. Another thing the reservation was made for payment at the hotel. There were several attempts on my ..."
Reviewed on Sep 13, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
CA $247
CA $365 total
Sep 28 - Sep 29
includes taxes & fees
8.8/10 Excellent! (1,790 reviews)
"The only beach on island is across the road and I love that about this location. Very small beach and not much to it, coming from Tampa we have better beaches. The location of hotel is 20-30 minutes away from the bars and restaurants. Good thing is they have a free shuttle running daily with helps ..."
Reviewed on Sep 13, 2026
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 vacation package cost?
From just CA $1,071, 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
CA $201
per traveller
Private Sandbar Adventure in Key West Backcountry
CA $692
per traveller
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- Mel Fisher Maritime Museum
- Visit Ramrod Key
- South Beach
- Florida Keys Eco - Discovery Center
- Anne's Beach
- Key West Shipwreck Museum
- Boca Chica Nude Beach
- Clarence S. Higgs Memorial Beach Park
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- Visit Little Torch Key
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- Mallory Square
- Visit Downtown Key West
- Visit Sugarloaf Key
- Sombrero Beach
- Duval Street
- Veterans Memorial Park & Beach
- Sunset Park Beach
- Calusa Beach
- Visit Big Torch Key
- Curry Hammock State Park
- Fort Zachary Taylor Historic State Park
- Marathon Vacations
- Southernmost Point
- Visit Cudjoe Key
- Visit Summerland Key
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- Crane Point Museum and Nature Center
- Visit Boca Chica Key
- Visit Big Pine Key
- Seven Mile Bridge
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- Visit Key West
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- Fort East Martello Museum and Gallery
- Key West Lighthouse and Keeper's Quarters Museum
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.