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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 reception area with a wooden sculpture, a reception desk, a computer, and a television.
A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.
A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

1. Sugar Loaf Lodge

Sugar Loaf Lodge
2.2 km from Upper Sugarloaf Sound
United States
morgan
CA $169
CA $190 total
includes taxes & fees
Oct 26 - Oct 27
Sugar Loaf Lodge
A wooden deck with a railing, wicker chairs, and a view of greenery.
A two-story house with a balcony and a staircase leading to the upper level.
A spacious living area with a large flat-screen TV, a sofa, and a dining area with bar stools.
A modern bedroom with a large bed, two windows, a ceiling fan, and a green bench.

2. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
1.8 km from Upper Sugarloaf Sound
United States
max
CA $428
CA $975 total
includes taxes & fees
Oct 27 - Oct 28
Starlight Serenity - Hideaway w Stunning Views
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 hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.
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
Jade
CA $157
CA $264 total
includes taxes & fees
Oct 29 - Oct 30
The Perry Hotel & Marina Key West
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 covered outdoor seating area with tables and chairs, overlooking a marina with boats.
A clear view of turquoise ocean water and a blue sky with clouds.

4. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
20.9 km from Upper Sugarloaf Sound
United States
Eric A
CA $174
CA $279 total
includes taxes & fees
Oct 21 - Oct 22
Hilton Key West Resort & Marina
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
A dining area with a table and chairs, a ceiling fan, a television, and a window with a view of the outdoors.
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.

5. Parmer's Resort

Parmer's Resort
16 km from Upper Sugarloaf Sound
United States
Mireya
CA $208
CA $281 total
includes taxes & fees
Nov 3 - Nov 4
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 row of houseboats docked at a marina with clear reflections in the water.
A floating houseboat with a covered deck and seating area, docked at a marina.

6. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
20.5 km from Upper Sugarloaf Sound
United States
Daisybel
CA $127
CA $342 total
includes taxes & fees
Oct 18 - Oct 19
Old Wooden Bridge Resort and Marina
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.
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.

7. Looe Key Reef Resort

Looe Key Reef Resort
14 km from Upper Sugarloaf Sound
United States
Stephen
CA $199
CA $224 total
includes taxes & fees
Oct 26 - Oct 27
Looe Key Reef Resort
A beachside resort with a wooden deck, palm trees, and a sunset view.
Room
A waterfront property with a large building featuring balconies, a pool area, and boats docked in the water.
A dining area with a round table and chairs, a potted plant, and a view of the ocean through large windows with shutters.

8. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
20.5 km from Upper Sugarloaf Sound
United States
Pawel
CA $461
CA $865 total
includes taxes & fees
Oct 19 - Oct 20
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 residential property with a swimming pool, a covered patio, and a view of the ocean.
A concrete pathway flanked by lush green foliage, leading to a shaded area.
A large house with a pool, surrounded by lush greenery.

9. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
4.7 km from Upper Sugarloaf Sound
United States
Preetam
CA $736
CA $1,388 total
includes taxes & fees
Oct 18 - Oct 19
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 residential building with a covered porch, surrounded by lush greenery and a well-maintained lawn.
A spacious kitchen with wooden cabinets, a large island, and modern appliances.

10. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
20.5 km from Upper Sugarloaf Sound
France
Karen
CA $1,092
CA $2,214 total
includes taxes & fees
Oct 25 - Oct 26
Capmar House by Brightwild Huge Home Pool
A modern kitchen with a central island, bar stools, and a large window.
A modern two-story house with a paved driveway and a well-maintained lawn.
A modern two-story house with a swimming pool, outdoor seating, and a well-maintained garden.
A modern two-story house with a swimming pool, outdoor seating, and a well-maintained garden.

11. Brand New Catchlight House With Private Pool

Brand New Catchlight House With Private Pool
20.6 km from Upper Sugarloaf Sound
CA $1,374
CA $2,890 total
includes taxes & fees
Oct 19 - Oct 20
Brand New Catchlight House With Private Pool
A spacious foyer with a wooden staircase, a console table with decorative items, and a view of the outdoors through a glass door.
A spacious kitchen with a dining area, large windows, and a view of the outdoors.
A modern kitchen with white cabinetry, a central island with bar stools, stainless steel appliances, and a view to the outside.
A spacious kitchen with white cabinets, a central island, and a dining area with chairs.

12. Evershore House Pool Parking Dock

Evershore House Pool Parking Dock
20.4 km from Upper Sugarloaf Sound
CA $1,092
CA $2,214 total
includes taxes & fees
Oct 18 - Oct 19
Evershore House Pool Parking Dock
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 two-story house with a front porch, a driveway, and palm trees.
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with seating.

13. Mirador House by Brightwild Pool Dock

Mirador House by Brightwild Pool Dock
20.5 km from Upper Sugarloaf Sound
CA $1,092
CA $2,456 total
includes taxes & fees
Oct 19 - Oct 20
Mirador House by Brightwild Pool Dock
A modern kitchen with white cabinetry, a stainless steel stove, and marble countertops.
A spacious kitchen with a large island, wooden flooring, and pendant lighting.
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.

14. New Altair House by Brightwild Pool Pets

New Altair House by Brightwild Pool Pets
20.5 km from Upper Sugarloaf Sound
CA $1,457
CA $2,983 total
includes taxes & fees
Oct 18 - Oct 19
New Altair House by Brightwild Pool Pets
A modern kitchen with a central island, bar stools, a large TV, and a built-in oven.
A two-story white house with a swimming pool, outdoor seating area, and a well-maintained lawn.
A spacious living area with a large dining table, white sofas, and a TV mounted on the wall.
A spacious dining area with a long wooden table, six chairs, and pendant lights.

15. Brand New Build Larkshine House - Pool

Brand New Build Larkshine House - Pool
20.6 km from Upper Sugarloaf Sound
CA $1,821
CA $3,393 total
includes taxes & fees
Oct 18 - Oct 19
Brand New Build Larkshine House - Pool
A modern house with a swimming pool, outdoor seating, and palm trees.
A spacious living area with a light blue sofa, a round coffee table, and a dining area with wooden chairs and a table.
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.

16. Floralee House in Key West

Floralee House in Key West
20.6 km from Upper Sugarloaf Sound
CA $1,457
CA $2,983 total
includes taxes & fees
Oct 18 - Oct 19
Floralee House in Key West
A modern kitchen with a large island, bar stools, and a view of the outdoors.
A modern bedroom with a large bed, a desk, a ceiling fan, and a window with curtains.
A two-story building with a symmetrical facade, a central entrance, and a car parked in front.
A modern living room with a large dining table, sofas, and a view of a body of water through large windows.

17. New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
20.4 km from Upper Sugarloaf Sound
CA $1,821
CA $3,482 total
includes taxes & fees
Oct 19 - Oct 20
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 lighting, and a view of the outdoors.
A spacious living area with a large dining table, comfortable seating, a wicker chandelier, and a view of palm trees through large windows.

18. The Joyrise House at Solaire Lunara Bay

The Joyrise House at Solaire Lunara Bay
20.3 km from Upper Sugarloaf Sound
CA $2,186
CA $3,893 total
includes taxes & fees
Oct 18 - Oct 19
The Joyrise House at Solaire Lunara Bay
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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
1,003 reviews
View
A wooden deck with a railing, wicker chairs, and a view of greenery.
Starlight Serenity - Hideaway w Stunning Views
10.0
Exceptional
1 review
View
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
The Perry Hotel & Marina Key West
9.4
Exceptional
1,307 reviews
View
A marina with boats docked, a pool area, and a building with a white facade.
Hilton Key West Resort & Marina
9.0
Wonderful
1,791 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
1,003 reviews
View

Hotels recommended for families near Upper Sugarloaf Sound

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.
A corridor lined with trees and potted plants, leading to a building with a white exterior and windows.
A beachside dining area with thatched umbrellas, white plastic chairs, and tables.

Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
CA $169
CA $190 total
includes taxes & fees
Oct 26 - Oct 27
Sugar Loaf Lodge
A wooden deck with a hanging hammock and a view of a green landscape.
A spacious living area with a kitchen island, a staircase, and large windows offering a view of the outdoors.
A spacious living room with a flat-screen TV, a sofa, a dining table, and large windows offering a view of greenery.
A modern kitchen with a central island, bar stools, and a dining area with a round table.

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
CA $328
CA $903 total
includes taxes & fees
Oct 27 - Oct 28
Starlight Serenity - Hideaway with Stunning Views
A wooden deck with a railing, wicker chairs, and a view of greenery.
A two-story house with a balcony and a staircase leading to the upper level.
A spacious living area with a large flat-screen TV, a sofa, and a dining area with bar stools.
A modern bedroom with a large bed, two windows, a ceiling fan, and a green bench.

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
Summerland Key
CA $428
CA $975 total
includes taxes & fees
Oct 27 - Oct 28
Starlight Serenity - Hideaway w Stunning Views
A two-story beachfront house with a balcony, a covered outdoor seating area, and a small boat dock.
A residential property with a swimming pool, a covered patio, and a view of the ocean.
A concrete pathway flanked by lush green foliage, leading to a shaded area.
A large house with a pool, surrounded by lush greenery.

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
Summerland Key
CA $736
CA $1,388 total
includes taxes & fees
Oct 18 - Oct 19
Atlantic View Luxury Villa with Pool
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A resort with a swimming pool, beach area, and marina.
A room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.
Outdoor dining

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
CA $178
CA $595 total
includes taxes & fees
Oct 16 - Oct 17
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
An aerial view of a resort with a large pool, palm trees, and a pier.
A two-story building with a balcony, a covered entrance, and a parking area with a bicycle.
A balcony with wicker furniture, a wooden table, and a view of the surrounding area.
An aerial view of a coastal residential area with multiple tennis courts, a marina, and houses with ocean views.

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
CA $498
CA $992 total
includes taxes & fees
Oct 26 - Oct 27
Spanish Queen @Venture Out, Cudjoe Key
A two-story house with a balcony, a staircase, and a view of the beach.
A waterfront property with a pool, palm trees, and a house with a balcony.
A beach with palm trees, a wooden dock, and lounge chairs.
A beach view with a swimming pool, palm trees, and lounge chairs.

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West

Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key
CA $462
CA $1,036 total
includes taxes & fees
Oct 19 - Oct 20
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A coastal residential area with houses, a marina, and a flag.
A marina with boats docked, a clear sky, and a calm waterway.
A resort with a swimming pool, beach area, and marina.

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Cudjoe Key
CA $284
CA $722 total
includes taxes & fees
Oct 27 - Oct 28
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Top Upper Sugarloaf Sound Hotel Reviews

Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

10/10 Excellent
"Friendly and helpful staff from the moment we entered the Sugarloaf KOA property (Thanks Elizabeth). It was so nice to come back to a cool and clean 2 bedroom cottage after a fun filled day of water activities. It was perfect for our family of 5."
Janice 4-night trip
Posted 6 hours ago
Sugarloaf Key RV Resort & Cottages
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"I cannot say enough good things about this property. The staff is incredibly friendly and helpful. The amenities are great and the hotel itself is very clean and fairly modern. We had three teenagers with us and we had a blast every day. We had bad weather, but there were still so many things to see and do in the area. The wildlife is so fun. There’s a whole family of Stone crabs that live behind the marina. There are tons of fish in the water to go visit every day. It was just so much fun. I’ve never stayed at a KOA campground or hotel before and was beyond pleasantly surprised."
Valerie 6-night trip
Posted 7 hours ago
Sugarloaf Key Hotel at KOA Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

8/10 Good
"Balcony"
Martin 1-night trip
Posted 1 day ago
Sugar Loaf Lodge
Private Secluded Ocean View & Pool Near Key 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!"
Bevan B. 4-night trip
Posted 5 days ago
Private Secluded Ocean View & Pool Near Key West
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 months 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 3 months ago
Oceanside, pet friendly, smart home with plenty of paddle equipment
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 4 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 4 months ago
Starlight Serenity - Hideaway w Stunning Views
Private and Exclusive Florida Keys Getaway

Private and Exclusive Florida Keys Getaway

10/10 Excellent
"Beautiful view and sweet natural beach/coastline. The pool was heavenly"
Susan H. 5-night trip
Posted 5 months ago
Private and Exclusive Florida Keys Getaway

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.
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.
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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 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.
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.

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