When you've finished up at this urban area in Sugarloaf Key, why not make your way to Florida Keys Beaches, Sugarloaf Beach, and Upper Sugarloaf Sound? They're not too far from Upper Sugarloaf Key and also a favorite with many travelers.
Upper Sugarloaf Key Tours
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Price found within the past 48 hours. Click for updated prices.
Creekside Inn
Save 100% on your flight
Price was $1,041, price is now $540 per person
$540
per person
May 26 - May 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.8/10 Good! (1,011 reviews)
Check-in was easy and welcoming. Easy parking. Room was very clean. Plenty of towels and toiletries. We had a lower level room on the canal. It was private and quiet. There was a table and chairs that allowed us the opportunity to sit outside in the evening. We had a pleasant stay.
Reviewed on Apr 22, 2026
Casablanca Miami Beach
North Beach
Price was $2,879, price is now $1,328 per person
$1,328
per person
Jun 23 - Jun 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (322 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 2026
Popular places to visit
Florida Keys Beaches
Nothing says vacation like spending a carefree day at Florida Keys Beaches, a popular beach in Long Beach Estates.
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Shark Key
Commune with nature and explore the great outdoors at Shark Key during your travels in Key West. In the area, take in the entertainment choices and beautiful sunsets.
Upper Sugarloaf Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
Venture Key
Commune with nature and explore the great outdoors at Venture Key during your travels in Summerland Key.
Crab Key
Commune with nature and explore the great outdoors at Crab Key during your travels in Summerland Key.
Best Lodging Options Near Upper Sugarloaf Key
Check availability on hotels close to Upper Sugarloaf Key
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
Sugarloaf Key RV Resort & Cottages
311 Johnson Rd Summerland Key FL
9BR Estate | 3 Homes & Pool | 30 Min to KW
Monroe County FL
Private Pool Oasis — 3 King Suites | 30 Min to Key West
Monroe County FL
Starlight Serenity - Hideaway w Stunning Views
Summerland Key FL
Starlight Serenity - Hideaway with Stunning Views
Summerland Key FL
Sublimely private luxury home with enveloping oceanfront views near Key West
Sugarloaf Key FL
Waterfront, Pet Friendly - Loggerhead Lagoon
Sugarloaf Key FL
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
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.
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