Sugarloaf Key Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Cavalier Hotel South Beach
South Beach
Price was CA $2,655, price is now CA $1,319 per person
CA $1,319
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
8.6/10 Excellent! (1,002 reviews)
I loved that it was an unique property & easily accessible to everything.
Reviewed on Nov 5, 2026
The Retreat Collection at 1 Hotel & Homes South Beach
South Beach
Price was CA $15,066, price is now CA $7,188 per person
CA $7,188
per person
Feb 1 - Feb 4
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) 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
The Marlin Hotel
South Beach
Price was CA $2,561, price is now CA $1,373 per person
CA $1,373
per person
Jan 17 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Miami (MIA)
9.2/10 Wonderful! (1,005 reviews)
Nice hotel. Room was clean. Bed and pillows very comfortable. Bathroom was tight but shower was nice.
There was some light that shown in from the back alley.
We didn’t like the fact that there was a mandatory $32.00 fee per person for a beach chair and towel. The weather was rainy but you still had to pay for it. Nice location a block to the beach. Lots of restaurants nearby.
Reviewed on Nov 4, 2026
YotelPad Miami
Downtown Miami
Price was CA $2,730, price is now CA $1,531 per person
CA $1,531
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Miami (MIA)
8.4/10 Very good! (543 reviews)
Hotel is in a good location if you are looking for one near the cruise port
Reviewed on Nov 2, 2026
Sugarloaf Key Hotel Deals
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
9.2/10 Wonderful! (41 reviews)
"Clean and quiet bungalow that is convenient to Key West but far enough away to enjoy the quiet."
Reviewed on Nov 4, 2026
Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $320 per night from Nov 30 to Dec 1
CA $320
CA $448 total
Nov 30 - Dec 1
includes taxes & fees
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 $205
per traveller
Private Sandbar Adventure in Key West Backcountry
CA $707
per traveller
Private Luxury Sandbar Excursion in Key West
CA $1,697
per traveller
Frequently asked questions
Explore a world of travel with Expedia
- Cabin Rentals in Boca Chica Key
- Cheap Hotels in Key West
- Save BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2
- Motel 6 Hotels in Key West
- Palm COTTAGE
- Hotel Wedding Venues Hotels in Cudjoe Key
- Kimpton Hotels in Lower Florida Keys
- Resorts in Cudjoe Key
- Tree Top Paradise
- Apartments in Sugarloaf Key
- Beautiful Family
- Villa Jekjak
- Beach Hotel Hotels in Cutthroat Harbor Estates
- All Inclusive Resorts and in Key West
- Summerland Key Hotels
- Condo Rentals in Key West
- Villas in Summerland Key
- Beach Hotel Hotels in Key West
- Beachfront 3B/3B Fishing Oasis
- Oceanfront Hotels in Key West
- Old Florida Style
- Key West Hotels
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Key West Intl.
- Flights to Summerland Key
- Flights from Summerland Key
- Flights from Miami (MIA) to Key West (EYW)
- Flights to Melody Key
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Vancouver (YVR) to Key West (EYW)
- Flights from Buffalo (BUF) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Ramrod Key
- Flights from Ottawa (YOW) to Key West (EYW)
- Flights from Montreal (YUL) to Key West (EYW)
- Flights from Toronto (YYZ) to Key West (EYW)
- Flights from Melody Key
- Flights from Edmonton (YEG) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights to Key West
- Flights from Calgary (YYC) to Key West (EYW)
- Visit Big Torch Key
- Florida Keys Eco - Discovery Center
- Anne's Beach
- Clarence S. Higgs Memorial Beach Park
- Visit Ramrod Key
- Marathon Vacations
- Duval Street
- All inclusive Vacation Packages Sugarloaf Key
- Calusa Beach
- Visit Key West
- Visit Cudjoe Key
- Veterans Memorial Park & Beach
- Mel Fisher Maritime Museum
- Visit Sugarloaf Key
- Fort Zachary Taylor Historic State Park
- All inclusive Vacation Packages Key West
- Key West Shipwreck Museum
- Seven Mile Bridge
- Harry S. Truman Little White House
- Crane Point Museum and Nature Center
- Boca Chica Nude Beach
- Southernmost Point
- Sunset Park Beach
- Curry Hammock State Park
- Sombrero Beach
- Visit Boca Chica Key
- Visit Big Pine Key
- South Beach
- Visit Little Torch Key
- Visit Summerland Key
- Key West Lighthouse and Keeper's Quarters Museum
- Fort East Martello Museum and Gallery
- All inclusive Vacation Packages Lower Florida Keys
- Smathers Beach
- Key West Vacations
- Mallory Square
- Beach Vacation Packages Cudjoe Key
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
