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
Visit Upper Sugarloaf Key
Plan a trip to see Upper Sugarloaf Key
Price found within the past 48 hours. Click for updated prices.
Bay Breeze Premium Apartments By Eskape Collection
Price was $1,516, price is now $696 per person
$696
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
The staff was courteous and helpful. The apartment was equipped with basic essentials. The area was quiet. I would suggest adding oven mittens in the kitchen as there was nothing to use to take the pan out of the oven with.
Reviewed on Jan 21, 2026
Casablanca Miami Beach
North Beach
Price was $1,234, price is now $590 per person
$590
per person
Apr 12 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (311 reviews)
I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly
Reviewed on Nov 12, 2025
Popular places to visit
Florida Keys Beaches
Why not spend a lazy afternoon at Florida Keys Beaches during your trip to 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 great live music 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
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Summerland Key FL
Soothing cabin in Sugarloaf Key
Summerland Key FL
Pelico Palms Estate.
Monroe County FL
The Sunset Suites of Pelico Palms
Monroe County FL
The Villa of Pelico Palms
Monroe County FL
Starlight Serenity - Hideaway w Stunning Views
Summerland Key FL
Sublimely private luxury home with enveloping oceanfront views near Key West
Near Key West FL
Starlight Serenity - Hideaway w/ Stunning Views
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.
Explore a world of travel with Expedia
- Key West Hotels
- Cudjoe Key Hotels
- RV Parks in Cudjoe Key
- Cottages in Cudjoe Key
- Resorts in Cudjoe Key
- Beach Hotels in Cudjoe Key
- Hotels with Restaurants in Cudjoe Key
- Villas in Cudjoe Key
- Pet-friendly Hotels in Cudjoe Key
- Cheap Hotels in Cudjoe Key
- Vacation Homes in Cudjoe Key
- 4 Star Hotels in Cudjoe Key
- Hilton Hotels in Cudjoe Key
- Fishing Resorts & in Cudjoe Key
- Motels in Cudjoe Key
- Condo Rentals in Cudjoe Key
- Houseboats in Cudjoe Key
- Historic Hotels in Cudjoe Key
- Hotels with a Pool in Cudjoe Key
- Sugarloaf Key Hotels
- Lower Sugarloaf Key Hotels
- Houseboats in Sugarloaf Key
- RV Parks in Sugarloaf Key
- Cottages in Sugarloaf Key
- Villas in Sugarloaf Key
- Cabin Rentals in Sugarloaf Key
- Oceanfront Hotels in Sugarloaf Key
- Cheap Hotels in Sugarloaf Key
- Apartments in Sugarloaf Key
- B&B in Sugarloaf Key
- Hotels & Resorts for Couples in Sugarloaf Key
- Condo Rentals in Sugarloaf Key
- All-inclusive Resorts in Sugarloaf Key
- Luxury Hotels in Sugarloaf Key
- Family Hotels in Sugarloaf Key
- Hilton Hotels in Sugarloaf Key
- Beach Hotels in Sugarloaf Key
- Hotels with Bars in Sugarloaf Key
- Hotels with Tennis Courts in Sugarloaf Key
- Resorts & Hotels with Spas in Sugarloaf Key
- 3 Star Hotels in Sugarloaf Key
- Guest Houses in Sugarloaf Key
- 4 Star Hotels in Sugarloaf Key
- Condo Resorts in Sugarloaf Key
- Hotels with a Pool in Sugarloaf Key
- Historic Hotels in Sugarloaf Key
- Resorts in Sugarloaf Key
- Lower Keys Hotels
- Fishing Resorts & in Lower Keys
- Cheap Hotels in Lower Keys
- Pet-friendly Hotels in Lower Keys
- Beach Hotels in Lower Keys
- Cottages in Lower Keys
- 5 Star Hotels in Lower Keys
- Resorts in Lower Keys
- Motels in Lower Keys
- Extended Stay Hotels in Lower Keys
- 4 Star Hotels in Lower Keys
- RV Parks in Lower Keys
- Apartments in Lower Keys
- Hotels with Hot Tubs in Lower Keys
- Ski Hotels in Lower Keys
- Bay Point Hotels
- Flights to Cudjoe Key
- Flights from Cudjoe Key
- Flights from Minneapolis - St. Paul to Cudjoe Key
- Flights from Boston to Cudjoe Key
- Flights from Raleigh to Cudjoe Key
- Flights from Tampa to Cudjoe Key
- Flights from Orlando to Cudjoe Key
- Flights from Lower Sugarloaf Key
- Flights to Sugarloaf Key
- Flights from New York to Sugarloaf Key
- Flights from Sugarloaf Key
- Flights to Lower Keys
- Car rentals near Cudjoe Key
- Budget Rental Cars in Cudjoe Key
- Enterprise Rental Cars in Cudjoe Key
- Sixt Rental Cars in Cudjoe Key
- Alamo Rent A Car Rental Cars in Cudjoe Key
- Fox Rental Cars Rental Cars in Cudjoe Key
- Thrifty Car Rental Rental Cars in Cudjoe Key
- Car rentals near Sugarloaf Key
- Enterprise Rental Cars in Sugarloaf Key
- Alamo Rent A Car Rental Cars in Sugarloaf Key
- Pickup Car Rentals in Sugarloaf Key
- Hertz Rental Cars in Sugarloaf Key