Sugarloaf Key Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Brickell Bay 3304
The W - Bayshore Unit 1003
Miami Downtown Condos
Casablanca Miami Beach
Brickell Bay 3505

Ready to book your vacation to Sugarloaf Key?

 

Choose your dates

Sugarloaf Key Hotel Deals

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (563 reviews)
Great place to enjoy

Reviewed on Apr 29, 2026

Sugarloaf Key Hotel at KOA Resort
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 $219 per night from May 25 to May 26
CA $219
CA $323 total
May 25 - May 26
includes taxes & fees
8.4/10 Very Good! (2,160 reviews)
Loved every second of our trip! Can’t wait to come back.

Reviewed on May 1, 2026

Blue Flamingo Resort Key West
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 $224 per night from May 11 to May 12
CA $224
CA $382 total
May 11 - May 12
includes taxes & fees
8.6/10 Excellent! (2,191 reviews)
Elevator was broken for several days. The staff definitely helped with our luggage for checkout but the rest of the time we used the stairs. Still not so bad but the gates on the stairs did not lock properly so it gives the impression of a property that is not well maintained.

Reviewed on Apr 30, 2026

Beachside Resort & Residences
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

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.