Sugarloaf Shores Vacations from $418
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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.
Broadmore Miami Beach
North Beach
Save 100% on your flight
Price was $853, price is now $418 per person
$418
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
5.6/10 (359 reviews)
Staff was exceptional during our entire stay, there was always someone at the front desk happy to help with any request.
Reviewed on Oct 13, 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $2,986, price is now $1,335 per person
$1,335
per person
Dec 31 - Jan 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (31 reviews)
Great hotel. Clearly freshly refurbished and excellent facilities. Staff were extremely attentive - everyone we bumped into in the lift, for example, even junior team members, asked how we were and whether there was anything that they could do to improve our stay. Shows a great culture! Only downsides are a bar that shuts very early (10pm) and a LOT of mosquitoes in the outdoor pool area - they give bug spray it we had to retreat late afternoon or after rain.
Reviewed on Oct 6, 2025
Bahama Beach Club Pompano
Price was $1,283, price is now $578 per person
$578
per person
Jan 1 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
10/10 Exceptional! (12 reviews)
Such a cute property with lots of charm and a great pool. We loved being able to walk to absolutely everything! The owners were so helpful in guiding us in things to do and how to best get around. We can’t wait to return.
Reviewed on Oct 15, 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
Oceans Edge Key West Resort, Hotel & Marina
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $212 total per night from Oct 28 to Oct 29
$212 total
Oct 28 - Oct 29
Total with taxes and fees
8.8/10 Excellent! (1,728 reviews)
"Exceeded our expectations. Restaurant was amazing, everything was clean and up to date. They kept open communication via text messages daily. I am a night shift health care provider, I cannot tell you how much I needed this mini-vacay."
Reviewed on Oct 9, 2025
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundable
$234 nightly
The price is $264 total per night from Oct 29 to Oct 30
$264 total
Oct 29 - Oct 30
Total with taxes and fees
8.6/10 Excellent! (2,787 reviews)
"The balcony was not private it was outside our front door located outside. Other then that it was a great stay!"
Reviewed on Oct 13, 2025
Margaritaville Beach House Key West
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$235 nightly
The price is $264 total per night from Oct 29 to Oct 30
$264 total
Oct 29 - Oct 30
Total with taxes and fees
8.6/10 Excellent! (1,777 reviews)
"Excellent experience"
Reviewed on Oct 12, 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.