
Sugarloaf Key Vacations from $654
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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.
The Latest Sugarloaf Key vacation packages
Price found within the past 48 hours. Click for updated prices.


Cavalier Hotel South Beach
South Beach
Price was $1,717, price is now $848 per person
$848
per person
Jan 11 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $15,566, price is now $7,804 per person
$7,804
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 $1,520, price is now $764 per person
$764
per person
Jan 11 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (1,005 reviews)
The room was great but did not have a valet as mentioned on website which made parking very complicated.
Reviewed on Nov 8, 2026

Don't see what you're looking for?
See all available trips from Columbus to Sugarloaf Key
View all tripsWhat to do in Sugarloaf Key

Private Marathon Backcountry Fishing Charter
$750
per adult

Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
$130
per adult
98% of travellers recommend
Sugarloaf Key Hotel Deals

Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (669 reviews)
"perfect place to enjoy the keys"
Reviewed on Nov 10, 2026

Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
9.2/10 Wonderful! (43 reviews)
"The cottage was clean and worked perfectly for our visit to the keys"
Reviewed on Nov 10, 2026

Margaritaville Beach House Key West
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$285 nightly
The price is $321 total per night from Nov 18 to Nov 19
$321 total
Nov 18 - Nov 19
Total with taxes and fees
8.8/10 Excellent! (1,822 reviews)
"."
Reviewed on Nov 10, 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.
Find the Best Sugarloaf Key Vacation Packages
Sugarloaf Key Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Key West Intl. Airport (EYW) |
Max Temp Winter | 75ºF |
Max Temp Summer | 85ºF |
Top Sights | Florida Keys Beaches, Boca Chica Nude Beach and Sugarloaf Beach |
More vacations you might like
Frequently asked questions
Explore a world of travel with Expedia
- Flights to Summerland Key
- Flights to Sugarloaf Key
- Flights to Cudjoe Key
- Delta Air Lines Atlanta (ATL) to Key West (EYW) flights
- Flights to Big Pine Key
- Flights to Little Torch Key
- Flights from Tampa (TPA) to Key West (EYW)
- JetBlue Airways Boston (BOS) to Key West (EYW) flights
- Flights to Key West Intl.
- Flights from Orlando (MCO) to Key West (EYW)
- Where to stay in Cudjoe Key
- Clarence S. Higgs Memorial
- Where to stay in Lower Sugarloaf Key
- Where to stay in Marathon
- Smathers Beach
- Big Pine Key Vacations
- Lower Florida Keys All Inclusive Vacation Packages
- Visit Little Torch Key
- Where to stay in Big Pine Key
- Lower Florida Keys All Inclusive Vacation Packages
- Cudjoe Key All Inclusive Vacation Packages
- Boca Chica Nude Beach
- Visit Summerland Key
- Visit Cudjoe Key
- Marathon Vacations
- Fort East Martello Museum
- Visit Big Pine Key
- Where to stay in Key Colony Beach
- Sugarloaf Key All Inclusive Vacation Packages
- Visit Boca Chica Key
- Visit Ramrod Key
- Lower Florida Keys All Inclusive Vacation Packages
- Key West Vacations
- Where to stay in Little Torch Key
- Visit Downtown Key West
- Lower Florida Keys All Inclusive Vacation Packages
- Long Key Vacations
- Where to stay in Key West
- Sugarloaf Key All Inclusive Vacation Packages
- Visit Lower Florida Keys
- Visit New Town
- Conch Key Vacations
- Lower Florida Keys All Inclusive Vacation Packages
- Where to stay in Boca Chica Key
- Key Colony Beach Vacations
- Visit Cow Key
- Cow Key Vacations
- Where to stay in Lower Florida Keys
- Old Town Key West Vacations
- Lower Florida Keys All Inclusive Vacation Packages
- Lower Florida Keys All Inclusive Vacation Packages
- Summerland Key Vacations
- Visit Sugarloaf Key
- Where to stay in Sugarloaf Key
- Lower Florida Keys All Inclusive Vacation Packages
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




















