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Our top choices for Upper Sugarloaf Sound hotels

A waterfront building with a flat roof, large windows, and a balcony.
A swimming pool with a surrounding deck, palm trees, and lounge chairs.
A beachside dining area with thatched umbrellas, white plastic chairs, and tables.
A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

1. Sugar Loaf Lodge

Sugar Loaf Lodge
2.2 km from Upper Sugarloaf Sound
United States
Marjorie
CA $164
CA $185 total
includes taxes & fees
Sep 15 - Sep 16
Sugar Loaf Lodge
A marina with boats docked, a pool area, and a building with a white facade.
A breakfast setting with a table, chairs, a vase with flowers, and a city view.
A marina with numerous boats docked, a swimming pool, and palm trees.
A hotel room with a balcony overlooking a marina and the ocean.

2. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
20.9 km from Upper Sugarloaf Sound
United States
Linda
CA $146
CA $246 total
includes taxes & fees
Sep 15 - Sep 16
Hilton Key West Resort & Marina
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.
A marina with boats docked, a swimming pool, and palm trees.

3. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
21.8 km from Upper Sugarloaf Sound
United States
Boyan
CA $188
CA $297 total
includes taxes & fees
Sep 24 - Sep 25
The Perry Hotel & Marina Key West
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.
A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

4. Looe Key Reef Resort

Looe Key Reef Resort
14 km from Upper Sugarloaf Sound
United States
Sarah
CA $93
CA $105 total
includes taxes & fees
Sep 23 - Sep 24
Looe Key Reef Resort
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.
A sunset view with a thatched structure and a palm tree by a calm body of water.

5. Parmer's Resort

Parmer's Resort
16 km from Upper Sugarloaf Sound
United States
Yuran
CA $231
CA $305 total
includes taxes & fees
Sep 21 - Sep 22
Parmer's Resort
A cozy room with a brown leather sofa, a white table, and a ceiling fan.
A compact kitchen with wooden beams, a dining area with white chairs, and a TV mounted on the wall.
A floating houseboat with a covered deck and seating area, docked at a marina.
A white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.

6. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
20.5 km from Upper Sugarloaf Sound
United States
abhimanyu
CA $124
CA $334 total
includes taxes & fees
Sep 27 - Sep 28
Old Wooden Bridge Resort and Marina
A beachside resort with a wooden deck, palm trees, and a sunset view.
A dining area with a round table and chairs, a potted plant, and a view of the ocean through large windows with shutters.
A waterfront property with a large building featuring balconies, a pool area, and boats docked in the water.

7. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
20.5 km from Upper Sugarloaf Sound
United States
Pawel
CA $415
CA $803 total
includes taxes & fees
Sep 13 - Sep 14
Grand Marina Suite by Brightwild Waterfront
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.
A concrete pathway flanked by lush green foliage, leading to a shaded area.
A residential property with a swimming pool, a covered patio, and a view of the ocean.
A large house with a pool, surrounded by lush greenery.

8. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
4.7 km from Upper Sugarloaf Sound
United States
Preetam
CA $708
CA $1,340 total
includes taxes & fees
Sep 21 - Sep 22
Atlantic View Luxury Villa with Pool
A white two-story house with a balcony and a swimming pool.
A balcony with a view of a swimming pool, palm trees, and a fenced yard.
A spacious kitchen with wooden cabinets, a large island, and modern appliances.
A residential building with a covered porch, surrounded by lush greenery and a well-maintained lawn.

9. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
20.5 km from Upper Sugarloaf Sound
France
Karen
CA $1,037
CA $2,175 total
includes taxes & fees
Sep 16 - Sep 17
Capmar House by Brightwild Huge Home Pool
A white two-story house with a central archway and a paved driveway.
A modern house with a swimming pool, lounge chairs, and a covered patio area.
A modern bathroom with a glass-enclosed shower, a white sink with black fixtures, and a large mirror.

10. Palmgale House in Key West

Palmgale House in Key West
20.6 km from Upper Sugarloaf Sound
CA $1,351
CA $2,892 total
includes taxes & fees
Sep 22 - Sep 23
Palmgale House in Key West
A modern house with a swimming pool, outdoor seating, and palm trees.
A dining area with a wooden table and chairs, large windows, and a view of the outdoors.
A covered outdoor seating area with white chairs and a ceiling fan, overlooking a swimming pool and a well-maintained lawn.
A spacious living area with a light blue sofa, a round coffee table, and a dining area with wooden chairs and a table.

11. Floralee House in Key West

Floralee House in Key West
20.6 km from Upper Sugarloaf Sound
CA $1,426
CA $2,979 total
includes taxes & fees
Sep 21 - Sep 22
Floralee House in Key West
A poolside area with lounge chairs, a wooden table, and palm trees.
A modern living room with a sectional sofa, a coffee table, and a view of the outdoor patio area.
A patio with white wicker furniture, palm trees, and a view of a lake.
A large, modern resort with multiple buildings, a central pool, and a marina.

12. The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
20.2 km from Upper Sugarloaf Sound
CA $2,157
CA $3,890 total
includes taxes & fees
Sep 23 - Sep 24
The Fairhaven House at Solaire Lunara Bay
A spacious kitchen with a large island, pendant lighting, and a dining area with a table and chairs.
A modern kitchen with a central island, bar stools, pendant lights, and a dining area with a sofa and chairs.
A two-story house with a swimming pool, outdoor seating, and a barbecue area.
A modern kitchen with white cabinetry, a central island, and pendant lighting.

13. New Windrose House by Brightwild Pool

New Windrose House by Brightwild Pool
20.6 km from Upper Sugarloaf Sound
CA $1,351
CA $2,892 total
includes taxes & fees
Sep 22 - Sep 23
New Windrose House by Brightwild Pool
A modern living room with a dark blue sectional sofa, a wooden coffee table, and a kitchen area with a blue backsplash and white cabinets.
A modern outdoor pool area with lounge chairs and umbrellas, surrounded by a well-maintained lawn and palm trees.
A bedroom with a large bed, a balcony with a view, and a door leading to another room.
A modern kitchen with white cabinetry, a central island, and a black and white backsplash.

14. Ebberly House by Brightwild Amazing Pool

Ebberly House by Brightwild Amazing Pool
20.6 km from Upper Sugarloaf Sound
CA $1,351
CA $2,892 total
includes taxes & fees
Sep 22 - Sep 23
Ebberly House by Brightwild Amazing Pool
A modern kitchen with a central island, wooden cabinets, a built-in oven, and a large window providing natural light.
A modern kitchen with a central island, bar stools, pendant lights, and a built-in TV.
A large white house with a swimming pool, outdoor seating, and a covered patio area.
A modern living room with a green sofa, two round white coffee tables, and a dining area with a table and chairs.

15. Brand New The Greenmoor House With Pool

Brand New The Greenmoor House With Pool
20.5 km from Upper Sugarloaf Sound
CA $1,689
CA $3,364 total
includes taxes & fees
Sep 22 - Sep 23
Brand New The Greenmoor House With Pool
A poolside area with lounge chairs and umbrellas, a pool, and a view of the ocean.
A multi-story white building with balconies, a swimming pool, and outdoor seating.
A modern living room with a sofa, two armchairs, a coffee table, and a dining area with a table and chairs.
A modern kitchen with a central island, bar stools, pendant lighting, and a large window providing natural light.

16. New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House
20.3 km from Upper Sugarloaf Sound
CA $2,029
CA $3,746 total
includes taxes & fees
Sep 22 - Sep 23
New Waterfront Home - Dreamside House
A modern kitchen with a central island, pendant lighting, and large windows offering a view of the outdoors.
A boat with people jumping into the water.
A modern bathroom with a large mirror, two sinks, a toilet, and a glass-enclosed shower.
A modern living room with a sectional sofa, a dining area with a large table, and a TV mounted on the wall.

17. Parking Pool Dock - Shellstone House

Parking Pool Dock - Shellstone House
20.2 km from Upper Sugarloaf Sound
CA $2,031
CA $3,752 total
includes taxes & fees
Sep 13 - Sep 14
Parking Pool Dock - Shellstone House
A modern kitchen with a large island, bar stools, and a view of the outdoors.
A two-story building with a symmetrical facade, a central entrance, and a car parked in front.
A modern bedroom with a large bed, a desk, a ceiling fan, and a window with curtains.
A modern hotel bedroom with a large bed, two bedside tables, a ceiling fan, and a view of the water.

18. New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
20.4 km from Upper Sugarloaf Sound
CA $2,010
CA $3,728 total
includes taxes & fees
Sep 13 - Sep 14
New Waterfront Home - Sunray House
A modern kitchen with a large island, bar stools, and pendant lighting.
A large, multi-story white house with a swimming pool, surrounded by lush greenery and palm trees.
A modern kitchen with a central island, pendant lights, and a view of the outdoors.
A modern kitchen with white cabinetry, a central island, and a dining area with a long table and chairs.

19. The Joyrise House at Solaire Lunara Bay

The Joyrise House at Solaire Lunara Bay
20.3 km from Upper Sugarloaf Sound
CA $2,027
CA $3,744 total
includes taxes & fees
Sep 13 - Sep 14
The Joyrise House at Solaire Lunara Bay
A spacious living area with a large sofa, a coffee table, and a view of a balcony with a railing.
A spacious living room with a dark blue sofa, a coffee table, and a staircase leading to the upper floor.
A spacious living area with a dining table and chairs, a staircase with white railings, and a view of the outdoors.
A staircase with white railings and beige steps leading to a landing.

20. Mastway House by Brightwild Pool Dock

Mastway House by Brightwild Pool Dock
20.3 km from Upper Sugarloaf Sound
CA $1,013
CA $2,146 total
includes taxes & fees
Sep 22 - Sep 23
Mastway House by Brightwild Pool Dock
View all properties

Compare popular hotels close to Upper Sugarloaf Sound

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A waterfront building with a flat roof, large windows, and a balcony.
Sugar Loaf Lodge
8.2
Very good
1,001 reviews
View
A cozy room with a brown leather sofa, a white table, and a ceiling fan.
Old Wooden Bridge Resort and Marina
8.6
Excellent
369 reviews
View
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
Parmer's Resort
9.0
Wonderful
1,011 reviews
View
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
Looe Key Reef Resort
7.6
Good
1,007 reviews
View
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.
Atlantic View Luxury Villa with Pool
7.4
Good
3 reviews
View

Top Upper Sugarloaf Sound Hotel Reviews

Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Amazing"
Julie 2-night trip
Posted 1 day ago
Sugar Loaf Lodge
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"Very good"
Rafael 2-night trip
Posted 1 day ago
Sugarloaf Key Hotel at KOA Resort
Casa Cudjoe: Tropical Canal Front Retreat on Cudjoe Key, Dockage, Boater's Paradise & Dog-Friendly!

Casa Cudjoe: Tropical Canal Front Retreat on Cudjoe Key, Dockage, Boater's Paradise & Dog-Friendly!

10/10 Excellent
"The property was very comfortable on the inside of the house. Access to the water was great. Boat docking situation was great. Kitchen very well equipped… a fish cleaning table would have been nice. Landscape maintenance needed help."
Carol A. 28-night trip
Posted 2 weeks ago
Casa Cudjoe: Tropical Canal Front Retreat on Cudjoe Key, Dockage, Boater's Paradise & Dog-Friendly!
Oceanside, pet friendly, smart home with plenty of paddle equipment

Oceanside, pet friendly, smart home with plenty of paddle equipment

10/10 Excellent
"nice location, lovely atmosphere in neighborhood"
jenny t. 31-night trip
Posted 2 months ago
Oceanside, pet friendly, smart home with plenty of paddle equipment
Florida Keys Beach Getaway

Florida Keys Beach Getaway

10/10 Excellent
"Man, this place was awesome. If it wasnt for the sea weed, we would never want or have a need to leave. Seaweed was thinning out towards the end of our trip, but man, this place was worth it. Tom, your a gem bud."
Justin R. 7-night trip
Posted 2 months ago
Florida Keys Beach Getaway
Stunning 3BR Lower Keys Remodel, Waterfront with 90-fT dock & private pool

Stunning 3BR Lower Keys Remodel, Waterfront with 90-fT dock & private pool

10/10 Excellent
"Great house in Cudjoe GardensWould definitely come back"
Bill M. 32-night trip
Posted 2 months ago
Stunning 3BR Lower Keys Remodel, Waterfront with 90-fT dock & private pool
Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views

10/10 Excellent
"The host team is amazing and very responsive. The house is very beautiful inside and out. We loved grilling downstairs, so much room down there. We loved our stay here because it was very secluded, unlike Key West, where you are on top of each other. The location is perfect because you can still make it down to Key West in 25 minutes for activities and food."
max 4-night trip
Posted 3 months ago
Starlight Serenity - Hideaway w Stunning Views
Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views

10/10 Excellent
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
Tom H. 9-night trip
Posted 5 months ago
Starlight Serenity - Hideaway with Stunning Views
Sublimely private luxury home with enveloping oceanfront views near Key West

Sublimely private luxury home with enveloping oceanfront views near Key West

10/10 Excellent
"We had a wonderful stay at this home. The property itself is absolutely stunning, with beautiful sunset views and a great layout that made it easy for everyone to spread out and relax. The pool was warm and inviting, and there was plenty of space for our group to enjoy both indoors and outdoors. The party room was fun for our teenagers and adults! One of the highlights was the location on the bay—the water is very shallow and incredibly calm, which made it perfect for relaxing and enjoying the surroundings. However, if you’re looking for ocean waves, you won’t get that here. The bedrooms were a pleasant surprise. Although there were no photos listed, they were all very spacious and each had its own en-suite bathroom, which added a lot of comfort and convenience for our group.There were just a couple of things to note. The upstairs bathrooms had low water pressure, which could be improved. Additionally, only four exterior cameras were disclosed in the listing; however, we counted seven cameras around the exterior of the home. Full and accurate disclosure of all cameras is important, and this discrepancy made us feel uncomfortable at times—especially traveling with teenage daughters.Overall, this is a beautiful home in a great setting, and we truly enjoyed our stay."
Natalie B. 8-night trip
Posted 6 months ago
Sublimely private luxury home with enveloping oceanfront views near Key West

Other attractions near Upper Sugarloaf Sound

A beach with a pier extending into the ocean during sunset.

Florida Keys Beaches

8.4/10 (858 reviews)
Nothing says vacation like spending a carefree day at Florida Keys Beaches, a popular beach in Long Beach Estates.
See properties
A motorcycle parked on a beach with palm trees and a clear sky.
Photo by Paul Devall

Sugarloaf Beach

8.4/10 (38 reviews)
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
See properties

Upper Sugarloaf Key

8.6/10 (54 reviews)
Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.
See properties

Squirrel Key

Commune with nature and explore the great outdoors at Squirrel Key during your travels in Summerland Key.
See properties

Venture Key

Commune with nature and explore the great outdoors at Venture Key during your travels in Summerland Key.
See properties

Frequently asked questions

What's the area like around Upper Sugarloaf Sound?
Upper Sugarloaf Sound is located in Summerland Key. Travelers like this budget-friendly area for its bars. You'll find 444 hotels and other accommodations within a few miles for a convenient home base.
Where is the best place to stay close to Upper Sugarloaf Sound?
Sugarloaf Key RV Resort & Cottages is one of the top choices for your stay based on our traveler data, and this vacation home offers an outdoor pool and free parking. It's located 1.5 mi (2.3 km) from Upper Sugarloaf Sound. Other good options within a few miles include Sugarloaf Key Hotel at KOA Resort and Sugar Loaf Lodge.
How many hotels will I find close to Upper Sugarloaf Sound?
Expedia has 444 hotels and other accommodations a few miles from Upper Sugarloaf Sound.
If I need to cancel the hotel reservation for my stay near Upper Sugarloaf Sound, will I receive a refund?
Yes! The majority of hotel bookings are fully refundable provided that you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of the scheduled arrival. If your reservation is non-refundable, you might be able to still cancel and be given a refund within 24 hours of your booking. Put your dates in and click on "Search", then you can filter by "fully refundable" to get the best deals near Upper Sugarloaf Sound.
What can I see and do near Upper Sugarloaf Sound?
Lounge by the water at Florida Keys Beaches and Sugarloaf Beach. At Upper Sugarloaf Key, Lower Sugarloaf Sound, and Venture Out Keys, you can surround yourself with nature. Venture Key and Out Key are both worth a visit while you're checking out the area.

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