Sugarloaf Key Vacation Packages
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Your Sugarloaf Key Vacation
From its highlights to its hidden gems, this city is best explored with a Sugarloaf Key vacation package. Check out hotels located in Sugarloaf Shores, which is good for families, fishing and views. Make your trip to Sugarloaf Key even more exciting by including some sightseeing. Florida Keys Beaches, Sugarloaf Beach and Upper Sugarloaf Sound are among the major attractions you'll want to explore. No matter your travel plans or budget, putting together the ultimate tailored Sugarloaf Key vacation is simple with Expedia.
Top Sugarloaf Key Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
CA $15,273
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) 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
Viscay Hotel
South Beach
CA $2,625
per person
Oct 11 - Oct 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8.2/10 Very good! (341 reviews)
Great location and great value. If you have an early flight before reception opens I’d suggest to arrange check out process beforehand
Reviewed on Jul 16, 2026
Ready to book your vacation to Sugarloaf Key?
Sugarloaf Key Hotel Deals
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (611 reviews)
"Overall it was a great experience. All staff is really kind. Our room had dogs hair on the floor when I first swept and bed isn’t too comfortable but room overall looks beautiful and is well maintained. Bar and pool close a bit early but like everything else in the keys. Only annoying thing is marina ..."
Reviewed on Jul 29, 2026
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
CA $192
CA $318 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (3,489 reviews)
"Disappointing Stay — Not What We Expected From a “Beach Resort” Unfortunately, our stay at Southernmost Beach Resort was very disappointing and did not live up to our expectations, particularly considering the price and how the property is marketed. The rooms were not up to the standard we expected ..."
Reviewed on Aug 8, 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.
What to do in Sugarloaf Key
Discover US East Coast Self Guided Audio Tour
CA $204
per traveller
Private Sandbar Adventure in Key West Backcountry
CA $772
per traveller
Frequently asked questions
How much does a Sugarloaf Key vacation package cost?
We make it simple to explore the world, with Sugarloaf Key vacation packages starting from just CA $683. You'll have the flexibility to combine your preferred hotels, airlines and car rental. For the ultimate getaway, why not add a couple of experiences and tours to your itinerary?
How do I get a cheap travel package to Sugarloaf Key?
Bundle your hotels and flights with Expedia to save big bucks on your next exciting adventure. With more than 550 airlines and 1,000,000 hotels across the globe, your Sugarloaf Key vacation package can be customized exactly to suit your budget. With all that extra cash, why not add one or more awesome experiences and tours? It's an easy way to unlock even more discounts. Your dream getaway to Sugarloaf Key is much closer than you thought!
Where should I stay in Sugarloaf Key?
It makes sense to stay near the action. Many travelers favor hotels around popular sights, like Florida Keys Beaches, Sugarloaf Beach and Upper Sugarloaf Sound.
What are the top hotels in Sugarloaf Key?
Sugar Loaf Lodge and Palms Resort - Green House are both well-liked options in the neighborhood of Sugarloaf Shores. If you want to stay in the Lower Sugarloaf Key area, consider getting a room at Paradise Found On Sugarloaf Key Please Call 704 or Tiki Palms - Amazing 4 Bedroom Sugarloaf Key Canal Home.
How far in advance should I book my Sugarloaf Key vacation?
Reserving your flight early with Expedia means one less thing to have to worry about. Many air carriers display prices up to 12 months in advance. Generally, this is the cheapest time to book. If circumstances have left you booking late, incredible deals to Sugarloaf Key are still known to appear in the weeks leading up to departure.
What does an Expedia Sugarloaf Key travel package include?
Expedia has everything you need to plan your Sugarloaf Key trip, but how you structure your package is your choice. Pick from any combination of rental cars, hotels and flights. After some tours or activities to keep you on the go? Once you've made your booking, you can add them too. Whatever your style or budget, there's a package to match your needs.
What should I know before booking a Sugarloaf Key travel package?
Bundling your bookings into a Sugarloaf Key vacation package is the most convenient way to organize your trip. Not only that, you'll save just for combining your flights, hotels and car rentals. Once you've booked, why not add on an activity or a tour?
If I'm not able to travel, can I cancel my Sugarloaf Key vacation package?
Don't worry if you're rethinking your Sugarloaf Key vacation package — you can cancel or change your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We know life can sometimes throw a spanner in the works, so look up our Customer Service Portal if that occurs. When you're ready to make changes, we'll be here to help.
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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.
