The Best Hotels Closest to Upper Sugarloaf Sound in Summerland Key for 2026

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Our top choices for Upper Sugarloaf Sound hotels

A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.

A swimming pool with a surrounding deck, palm trees, and lounge chairs.

A waterfront building with a flat roof, large windows, and a balcony.

A reception area with a wooden sculpture, a reception desk, a computer, and a television.

1. Sugar Loaf Lodge

2.2 km from Upper Sugarloaf Sound

Mariia

SAR 447

SAR 503 total

includes taxes & fees

26 Oct - 27 Oct

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

A white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.

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.

2. Old Wooden Bridge Resort and Marina

20.5 km from Upper Sugarloaf Sound

Daisybel

SAR 334

SAR 904 total

includes taxes & fees

26 Oct - 27 Oct

A covered deck with chairs and umbrellas overlooking a beach.

A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.

A sunset view with a thatched structure and a palm tree by a calm body of water.

A dining area with a table and chairs, a ceiling fan, a television, and a window with a view of the outdoors.

3. Parmer's Resort

16 km from Upper Sugarloaf Sound

Mireya

SAR 503

SAR 689 total

includes taxes & fees

1 Nov - 2 Nov

A tropical resort with palm trees, a pool, and a wooden building.

A canal with boats docked on both sides, surrounded by lush greenery and trees.

A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

A spacious indoor dining area with multiple tables and chairs, ceiling fans, and a bar area.

4. Looe Key Reef Resort

14 km from Upper Sugarloaf Sound

Stephen

SAR 544

SAR 612 total

includes taxes & fees

26 Oct - 27 Oct

A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.

A bedroom with a large bed, a ceiling fan, and a balcony with a view of greenery.

A large house with a pool, surrounded by lush greenery.

A residential property with a swimming pool, a covered patio, and a view of the ocean.

5. Atlantic View Luxury Villa with Pool

4.7 km from Upper Sugarloaf Sound

Preetam

SAR 1,942

SAR 3,663 total

includes taxes & fees

26 Oct - 27 Oct

A marina with boats docked, a pool area, and a building with a white facade.

A clear view of turquoise ocean water and a blue sky with clouds.

A covered outdoor seating area with tables and chairs, overlooking a marina with boats.

A poolside dining area with round tables, chairs, and a pool in the background.

6. Hilton Key West Resort & Marina

20.9 km from Upper Sugarloaf Sound

Eric A

SAR 438

SAR 712 total

includes taxes & fees

28 Oct - 29 Oct

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

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.

A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

7. The Perry Hotel & Marina Key West

21.8 km from Upper Sugarloaf Sound

Jade

SAR 413

SAR 684 total

includes taxes & fees

1 Nov - 2 Nov

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 and a covered area, boats docked in front, and palm trees in the background.

8. Grand Marina Suite by Brightwild Waterfront

20.5 km from Upper Sugarloaf Sound

Pawel

SAR 1,218

SAR 2,282 total

includes taxes & fees

26 Oct - 27 Oct

A white two-story house with a balcony and a swimming pool.

A spacious kitchen with wooden cabinets, a large island, and modern appliances.

A spacious living area with a wooden dining table, comfortable seating, a flat-screen TV, and a ceiling fan.

A residential building with a covered porch, surrounded by lush greenery and a well-maintained lawn.

9. Capmar House by Brightwild Huge Home Pool

20.5 km from Upper Sugarloaf Sound

Karen

SAR 2,883

SAR 5,845 total

includes taxes & fees

29 Oct - 30 Oct

A spacious kitchen with a large island, white cabinetry, and pendant lighting.

A spacious living room with a large flat-screen TV, comfortable seating, a coffee table, and a sliding glass door leading to an outdoor patio.

A modern kitchen with white cabinets, a central island, and pendant lighting.

A pool area with a covered deck, palm trees, and a house with a balcony.

10. Aquaria House by Brightwild Pool Boat Dock

20.4 km from Upper Sugarloaf Sound

SAR 2,883

SAR 5,845 total

includes taxes & fees

1 Nov - 2 Nov

A two-story house with a swimming pool, surrounded by greenery and palm trees.

A two-story house with a covered porch, a front lawn, and palm trees.

A modern living room with a large TV, comfortable seating, and a balcony with a view.

A spacious kitchen with a large island, grey cabinets, and pendant lighting.

11. Seagate House by Brightwild Waterfront w Dock

20.5 km from Upper Sugarloaf Sound

SAR 2,883

SAR 5,845 total

includes taxes & fees

3 Nov - 4 Nov

A living room with two sofas, a coffee table, and a view of the outdoors.

A spacious kitchen with modern appliances, a dining area with a large table and chairs, and a view of the outdoors through large windows.

A two-story house with a swimming pool, white railings, and a covered patio area.

A two-story house with a front porch, a double door, and a number '8' on the door.

12. Waterlane House by Brightwild Pool Boat Dock

20.5 km from Upper Sugarloaf Sound

SAR 2,883

SAR 5,845 total

includes taxes & fees

3 Nov - 4 Nov

A poolside area with lounge chairs and umbrellas, a wooden deck, and a view of a body of water.

A modern living room with a white coffee table, a TV on the wall, and a dining area with wooden chairs and a black table.

A modern multi-story residential building with a swimming pool, outdoor seating, and lush landscaping.

A modern kitchen with a large island, wooden cabinets, and pendant lighting.

13. Waterfront Luxury Home - Tidelands House

20.3 km from Upper Sugarloaf Sound

SAR 4,808

SAR 9,193 total

includes taxes & fees

3 Nov - 4 Nov

A two-story house with a pool, surrounded by palm trees and a clear sky.

A covered outdoor area with a pool, white furniture, and ceiling fans.

A modern living room with a sofa, coffee table, and a rug. There is a kitchen area with a bar and seating.

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with seating.

14. Mirador House by Brightwild Pool Dock

20.5 km from Upper Sugarloaf Sound

SAR 2,883

SAR 6,483 total

includes taxes & fees

29 Oct - 30 Oct

A spacious living area with a wooden dining table, comfortable seating, a flat-screen TV, and large windows offering a view of the outdoors.

A two-story house with a swimming pool, surrounded by lush greenery and a fenced yard.

A two-story house with a swimming pool, outdoor seating, and a fenced yard.

A modern kitchen with white cabinetry, stainless steel appliances, and a central island with chairs.

15. Spindrift House by Brightwild Huge Pool Dock

20.5 km from Upper Sugarloaf Sound

SAR 2,883

SAR 5,845 total

includes taxes & fees

2 Nov - 3 Nov

A modern kitchen with white cabinetry, a marble countertop, and a central island with bar stools.

A two-story white building with a swimming pool, outdoor seating, and a staircase leading to the upper floor.

A modern kitchen with white cabinets, a wooden countertop, and a hanging pendant light.

A spacious kitchen with a large island, wooden flooring, and pendant lighting.

16. New Altair House by Brightwild Pool Pets

20.5 km from Upper Sugarloaf Sound

SAR 3,846

SAR 7,873 total

includes taxes & fees

28 Oct - 29 Oct

A spacious kitchen with a marble island, pendant lighting, and a dining area with chairs and a table.

A modern kitchen with white cabinetry, a large island, pendant lighting, and a view of greenery outside.

A modern living room with a sofa, coffee table, and a chessboard. There is a kitchen in the background with a stove, microwave, and cabinets.

A two-story house with a pool, surrounded by a well-maintained lawn and palm trees.

17. New Crestwood House by Brightwild Huge Pool

20.5 km from Upper Sugarloaf Sound

SAR 3,846

SAR 7,873 total

includes taxes & fees

28 Oct - 29 Oct

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 kitchen with white cabinetry, a central island, and a black and white backsplash.

A bedroom with a large bed, a balcony with a view, and a door leading to another room.

A modern outdoor pool area with lounge chairs and umbrellas, surrounded by a well-maintained lawn and palm trees.

18. Ebberly House by Brightwild Amazing Pool

20.6 km from Upper Sugarloaf Sound

SAR 3,846

SAR 7,873 total

includes taxes & fees

26 Oct - 27 Oct

A modern kitchen with a central island, bar stools, a large TV, and a built-in oven.

A spacious living area with a large dining table, white sofas, and a TV mounted on the wall.

A modern two-story house with a swimming pool, outdoor seating, and a well-maintained garden.

A spacious dining area with a long wooden table, six chairs, and pendant lights.

19. Brand New Build Larkshine House - Pool

20.6 km from Upper Sugarloaf Sound

SAR 4,808

SAR 8,956 total

includes taxes & fees

29 Oct - 30 Oct

A spacious kitchen with a large island, pendant lighting, and a dining area with a table and chairs.

A two-story house with a swimming pool, outdoor seating, and a barbecue area.

A modern kitchen with a central island, bar stools, pendant lights, and a dining area with a sofa and chairs.

A modern kitchen with white cabinetry, a central island, and pendant lighting.

20. New Windrose House by Brightwild Pool

20.6 km from Upper Sugarloaf Sound

SAR 3,846

SAR 7,873 total

includes taxes & fees

17 Nov - 18 Nov

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Compare popular hotels close to Upper Sugarloaf Sound

Property	Property class	Guest rating
Sugar Loaf Lodge	8.2 Very good 1,000 reviews	View
Old Wooden Bridge Resort and Marina	8.6 Excellent 376 reviews	View
Parmer's Resort	9.0 Wonderful 1,001 reviews	View
Looe Key Reef Resort	7.8 Good 1,000 reviews	View
Atlantic View Luxury Villa with Pool	7.4 Good 3 reviews	View

Top Upper Sugarloaf Sound Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"Hidden gem! My husband and I stayed 3 nights and this place exceeded expectations. There was ample space in the suite and the kitchenette was a huge bonus. We will absolutely stay here again."

Sugarloaf Key RV Resort & Cottages

10/10 Excellent

"Great"

Sugar Loaf Lodge

10/10 Excellent

"Very cute place, like at home, the lady on the desk is very sweet and helpful. Good price and close to Kea West."

Private Secluded Ocean View & Pool Near Key West

10/10 Excellent

"Everything was great! The house and the pool were clean and the basketball goal was an added plus! We wished that there were pool/beach towels in the house, but other than that everything was perfect!"

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."

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

10/10 Excellent

"Great house in Cudjoe GardensWould definitely come back"

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."

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!"

Waterfront home with a large dock, pool, and deck area. Can accommodate pets.

10/10 Excellent

"This was a lovely home and there was great communication with the host."

Other attractions near Upper Sugarloaf Sound

A wooden signpost with city names and distances, a beach with umbrellas, and lounge chairs.

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.

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A motorcycle parked on a beach with palm trees and a clear sky.

Sugarloaf Beach

8.4/10 (38 reviews)

Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?

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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.

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Squirrel Key

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

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Venture Key

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

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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 446 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 Hotel at KOA Resort is one of the top choices for your stay based on our traveler data, and this hotel offers a marina and a private beach. It's located 1.8 mi (2.9 km) from Upper Sugarloaf Sound. Other good options within a few miles include Sugarloaf Key RV Resort & Cottages and Sugar Loaf Lodge.

How many hotels will I find close to Upper Sugarloaf Sound?

Expedia has 446 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.

Where can I learn more about changing or cancelling my trip in the area near Upper Sugarloaf Sound?

For additional details about updating your stay near Upper Sugarloaf Sound or cancelling it, head over to our customer service page.

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. Out Key and Venture Key are both worth a visit while you're checking out the area.

Find hotels near Upper Sugarloaf Sound, Summerland Key from SAR 503

Change your mind

Treat yourself

Be picky

Check prices for these dates

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Star rating

Guest rating

Our top choices for Upper Sugarloaf Sound hotels

1. Sugar Loaf Lodge

2. Old Wooden Bridge Resort and Marina

3. Parmer's Resort

4. Looe Key Reef Resort

5. Atlantic View Luxury Villa with Pool

6. Hilton Key West Resort & Marina

7. The Perry Hotel & Marina Key West

8. Grand Marina Suite by Brightwild Waterfront

9. Capmar House by Brightwild Huge Home Pool

10. Aquaria House by Brightwild Pool Boat Dock

11. Seagate House by Brightwild Waterfront w Dock

12. Waterlane House by Brightwild Pool Boat Dock

13. Waterfront Luxury Home - Tidelands House

14. Mirador House by Brightwild Pool Dock

15. Spindrift House by Brightwild Huge Pool Dock

16. New Altair House by Brightwild Pool Pets

17. New Crestwood House by Brightwild Huge Pool

18. Ebberly House by Brightwild Amazing Pool

19. Brand New Build Larkshine House - Pool

20. New Windrose House by Brightwild Pool

Compare popular hotels close to Upper Sugarloaf Sound

Top Upper Sugarloaf Sound Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key RV Resort & Cottages

Sugar Loaf Lodge

Private Secluded Ocean View & Pool Near Key West

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

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

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway with Stunning Views

Waterfront home with a large dock, pool, and deck area. Can accommodate pets.

Other attractions near Upper Sugarloaf Sound

Florida Keys Beaches

Sugarloaf Beach

Upper Sugarloaf Key

Squirrel Key

Venture Key

Frequently asked questions