Sugarloaf Shores Vacation Packages 2026 from $485

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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.

Bahama Beach Club Pompano

Save 100% on your flight

$485

per person

Oct 7 - Oct 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.8/10 Exceptional! (47 reviews)

The Retreat Collection at 1 Hotel & Homes South Beach

South Beach

$5,714

per person

Nov 17 - Nov 20

found 1 day ago

Roundtrip non-stop 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 Local House

South Beach

Save 100% on your flight

$927

per person

Oct 17 - Oct 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

9.2/10 Wonderful! (1,000 reviews)

Great location on Ocean Drive, few mins walk to the main restaurants/bars. Rooftop pool was lovely after a day at the beach. Great to have sunbeds/towels provided for the beach which is a 5 minute walk across the road. Room was really nice with coffee machine and great view from the balcony. Check in was easy, 100$ security deposit for each night n weed to be paid which I don’t know about. Would 10000% stay again.

Reviewed on Aug 29, 2026

Brickell Arch Sea View Balcony Free Parking by Palermo Home Miami

Brickell

Save 100% on your flight

$806

per person

Nov 19 - Nov 26

found 6 hours ago

Roundtrip non-stop flight included

Philadelphia (PHL) to Miami (MIA)

10/10 Exceptional! (2 reviews)

Great

Reviewed on Jul 28, 2026

Viscay Hotel

South Beach

$2,146

per person

Nov 7 - Nov 14

found 21 hours ago

Roundtrip flight included

Boston (BOS) to Miami (MIA)

8.2/10 Very Good! (341 reviews)

Great location and great value. If you have an early flight before reception opens I’d suggest to arrange check out process beforehand

Reviewed on Jul 16, 2026

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

A calm lake with several white birds, including herons and pelicans, on the water's edge.

Cutthroat Harbor Estates

While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Venture Key are some notable places to visit nearby.

Boat traveling under the Seven Mile Bridge, Florida Keys, USA

Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Florida Keys Beaches, some noteworthy sights in the nearby area.

An aerial view of a coastal area with a long bridge connecting two landmasses, clear turquoise waters, and a clear blue sky with scattered clouds.

Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Venture Out Keys are some notable places to visit nearby.

Sugarloaf Shores Hotel Deals

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$210 nightly

$237 total

Sep 8 - Sep 9

Total with taxes and fees

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$125 nightly

$141 total

Sep 29 - Sep 30

Total with taxes and fees

8.2/10 Very Good! (2,362 reviews)

"Todo Super bien; el personal que trabaja en la instalación te hacen sentir como en casa muy acogedor; tranquilo y un servicio increíble"

Reviewed on Aug 30, 2026

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$195 nightly

$220 total

Aug 31 - Sep 1

Total with taxes and fees

See all 3,415 properties in Sugarloaf Shores

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.