Sugarloaf Shores Vacations from $425
Book a Hotel + Flight or Car together to unlock savings
Your Sugarloaf Shores Vacation
Your next big journey is calling out to you with a vacation package to Sugarloaf Shores. Excitement, fun and great times — you're bound to find it in this neighborhood. When the time comes to see the sights, your trip to Sugarloaf Shores has to include a visit to Sugarloaf Beach and Upper Sugarloaf Sound. Expedia is here to help put your travel plans into action. Book your ultimate Sugarloaf Shores vacation today.
The Latest Sugarloaf Shores Vacation Packages
Price found within the past 48 hours. Click for updated prices.
President Villa
South Beach
Save 100% on your flight
Price was $1,013, price is now $507 per person
$507
per person
Oct 30 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,000 reviews)
Hospitable staff, clean, location ideal to walking distance to beach and shopping.
Safe place!
Reviewed on Aug 8, 2025
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 Upper Sugarloaf Key are some notable places to visit nearby.
Sugarloaf Shores Hotel Deals
Beachside Resort & Residences
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$184 nightly
The price is $207 total per night from Sep 2 to Sep 3
$207 total
Sep 2 - Sep 3
Total with taxes and fees
8.4/10 Very Good! (1,479 reviews)
"The property was excellent, located in the heart of everything!! 😍"
Reviewed on Aug 23, 2025
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $247 total per night from Sep 1 to Sep 2
$247 total
Sep 1 - Sep 2
Total with taxes and fees
8.8/10 Excellent! (1,729 reviews)
"Excellent service"
Reviewed on Aug 25, 2025
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$132 nightly
The price is $149 total per night from Sep 2 to Sep 3
$149 total
Sep 2 - Sep 3
Total with taxes and fees
7.8/10 Good! (1,070 reviews)
"Most excellent facility with very accommodating staff."
Reviewed on Aug 18, 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.