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Find hotels near Upper Sugarloaf Sound, Summerland Key from CA $162

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

1. Sugar Loaf Lodge

Sugar Loaf Lodge
2.2 km from Upper Sugarloaf Sound
United States
morgan
CA $170
CA $191 total
includes taxes & fees
Oct 13 - Oct 14
Sugar Loaf Lodge
A wooden deck with a railing, wicker chairs, and a view of greenery.
A modern bedroom with a large bed, two windows, a ceiling fan, and a green bench.
A modern kitchen with a large island, white cabinetry, and three wicker bar stools.
A spacious living area with a large flat-screen TV, a sofa, and a dining area with bar stools.

2. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
1.8 km from Upper Sugarloaf Sound
United States
max
CA $390
CA $959 total
includes taxes & fees
Oct 14 - Oct 15
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 hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.
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.

3. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
21.8 km from Upper Sugarloaf Sound
United States
Jade
CA $158
CA $264 total
includes taxes & fees
Oct 26 - Oct 27
The Perry Hotel & Marina Key West
A marina with boats docked, a pool area, and a building with a white facade.
A marina with numerous boats docked, a swimming pool, and palm trees.
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
Sweden
Anders
CA $186
CA $293 total
includes taxes & fees
Oct 26 - Oct 27
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.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.

5. Parmer's Resort

Parmer's Resort
16 km from Upper Sugarloaf Sound
United States
Mireya
CA $209
CA $282 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 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.
A row of houseboats docked at a marina with clear reflections in the water.

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 $343 total
includes taxes & fees
Oct 13 - Oct 14
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 canal with boats docked on both sides, surrounded by lush greenery and trees.
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.

7. Looe Key Reef Resort

Looe Key Reef Resort
14 km from Upper Sugarloaf Sound
United States
Stephen
CA $144
CA $162 total
includes taxes & fees
Oct 14 - Oct 15
Looe Key Reef Resort
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 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.

8. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
4.7 km from Upper Sugarloaf Sound
United States
Preetam
CA $738
CA $1,391 total
includes taxes & fees
Oct 13 - Oct 14
Atlantic View Luxury Villa with Pool
A beachside resort with a wooden deck, palm trees, and a sunset view.
Room
Room
A waterfront property with a large building featuring balconies, a pool area, and boats docked in the water.

9. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
20.5 km from Upper Sugarloaf Sound
United States
Pawel
CA $487
CA $895 total
includes taxes & fees
Oct 14 - Oct 15
Grand Marina Suite by Brightwild Waterfront
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.

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 $1,154
CA $2,339 total
includes taxes & fees
Oct 13 - Oct 14
Capmar House by Brightwild Huge Home Pool
A spacious living area with a blue sofa, a grey armchair, and a wooden coffee table. Large sliding glass doors lead to a pool and outdoor furniture.
A modern kitchen with a central island, stainless steel appliances, and pendant lighting.
A spacious living room with a large TV, blue sofas, and a wooden coffee table.
A spacious living area with a dining table and chairs, a kitchen with white cabinets, and a large window overlooking a scenic view.

11. Suncoast House by Brightwild Pool Boat Dock

Suncoast House by Brightwild Pool Boat Dock
20.5 km from Upper Sugarloaf Sound
CA $1,154
CA $2,595 total
includes taxes & fees
Oct 19 - Oct 20
Suncoast House by Brightwild Pool Boat Dock
A modern kitchen with a large island, bar stools, and pendant lighting.
A modern kitchen with white cabinetry, a central island, and a dining area with a long table and chairs.
A large, multi-story white house with a swimming pool, surrounded by lush greenery and palm trees.
A spacious living area with a large dining table, comfortable seating, a wicker chandelier, and a view of palm trees through large windows.

12. The Joyrise House at Solaire Lunara Bay

The Joyrise House at Solaire Lunara Bay
20.3 km from Upper Sugarloaf Sound
CA $2,309
CA $4,112 total
includes taxes & fees
Oct 13 - Oct 14
The Joyrise House at Solaire Lunara Bay
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 resort with a well-maintained lawn, outdoor seating area, and a large building with multiple floors.
A modern kitchen with a central island, bar stools, pendant lighting, and a large window providing natural light.

13. New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House
20.3 km from Upper Sugarloaf Sound
CA $1,924
CA $3,679 total
includes taxes & fees
Oct 13 - Oct 14
New Waterfront Home - Dreamside House
BBQ/picnic area
A hotel room with a large bed, a ceiling fan, a window with curtains, a bedside table with a lamp, and a patterned wall.
A white two-story house with a central archway and a paved driveway.
A modern bathroom with a glass-enclosed shower, a white sink with black fixtures, and a large mirror.

14. Palmgale House in Key West

Palmgale House in Key West
20.6 km from Upper Sugarloaf Sound
CA $1,539
CA $3,151 total
includes taxes & fees
Oct 13 - Oct 14
Palmgale House in Key West
A modern kitchen with a central island, bar stools, and a large window.
A modern two-story house with a swimming pool, outdoor seating, and a well-maintained garden.
A modern living space with a large wooden dining table, a sofa set, and a kitchen area.
A modern two-story house with a swimming pool, outdoor seating, and a well-maintained garden.

15. Brand New Catchlight House With Private Pool

Brand New Catchlight House With Private Pool
20.6 km from Upper Sugarloaf Sound
CA $1,452
CA $3,052 total
includes taxes & fees
Oct 13 - Oct 14
Brand New Catchlight House With Private Pool
A modern kitchen with a large island, bar stools, and a view of the outdoors.
A modern living room with a large dining table, sofas, and a view of a body of water through large windows.
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.

16. New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
20.4 km from Upper Sugarloaf Sound
CA $1,924
CA $3,679 total
includes taxes & fees
Oct 13 - Oct 14
New Waterfront Home - Sunray House
A modern kitchen with white cabinetry, a marble countertop, and a central island with bar stools.
A spacious kitchen with a large island, wooden flooring, and pendant lighting.
A two-story white building with a swimming pool, outdoor seating, and a staircase leading to the upper floor.
Room

17. New Altair House by Brightwild Pool Pets

New Altair House by Brightwild Pool Pets
20.5 km from Upper Sugarloaf Sound
CA $1,539
CA $3,151 total
includes taxes & fees
Oct 13 - Oct 14
New Altair House by Brightwild Pool Pets
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 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.
A modern kitchen with a large island, pendant lighting, and a backsplash with blue tiles.

18. Ebberly House by Brightwild Amazing Pool

Ebberly House by Brightwild Amazing Pool
20.6 km from Upper Sugarloaf Sound
CA $1,539
CA $3,151 total
includes taxes & fees
Oct 13 - Oct 14
Ebberly House by Brightwild Amazing Pool
A spacious kitchen with a marble island, pendant lighting, and a dining area with chairs and a table.
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.
A two-story house with a pool, outdoor seating, and a covered patio.

19. New Crestwood House by Brightwild Huge Pool

New Crestwood House by Brightwild Huge Pool
20.5 km from Upper Sugarloaf Sound
CA $1,539
CA $3,151 total
includes taxes & fees
Oct 13 - Oct 14
New Crestwood House by Brightwild Huge Pool
A modern kitchen with a central island, wooden cabinets, a built-in oven, and a large window providing natural light.
A large white house with a swimming pool, outdoor seating, and a covered patio area.
A modern kitchen with a central island, bar stools, pendant lights, and a built-in TV.
A modern living room with a green sofa, two round white coffee tables, and a dining area with a table and chairs.

20. Brand New The Greenmoor House With Pool

Brand New The Greenmoor House With Pool
20.5 km from Upper Sugarloaf Sound
CA $1,924
CA $3,679 total
includes taxes & fees
Oct 13 - Oct 14
Brand New The Greenmoor House With Pool
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
1,002 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
1,316 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
1,803 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
1,002 reviews
View

Hotels recommended for families near Upper Sugarloaf Sound

A waterfront building with a flat roof, large windows, and a balcony.
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.
A swimming pool with a surrounding deck, palm trees, and lounge chairs.

Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
CA $170
CA $191 total
includes taxes & fees
Oct 13 - Oct 14
Sugar Loaf Lodge
A wooden deck with a hanging hammock and a view of a green landscape.
A modern kitchen with a central island, bar stools, and a dining area with a round table.
A spacious living room with a flat-screen TV, a sofa, a dining table, and large windows offering a view of greenery.
A spacious living area with a kitchen island, a staircase, and large windows offering a view of the outdoors.

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
CA $284
CA $853 total
includes taxes & fees
Oct 14 - Oct 15
Starlight Serenity - Hideaway with Stunning Views
A wooden deck with a railing, wicker chairs, and a view of greenery.
A modern bedroom with a large bed, two windows, a ceiling fan, and a green bench.
A modern kitchen with a large island, white cabinetry, and three wicker bar stools.
A spacious living area with a large flat-screen TV, a sofa, and a dining area with bar stools.

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
Summerland Key
CA $390
CA $959 total
includes taxes & fees
Oct 14 - Oct 15
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 concrete pathway flanked by lush green foliage, leading to a shaded area.
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.

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
Summerland Key
CA $738
CA $1,391 total
includes taxes & fees
Oct 13 - Oct 14
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.
Outdoor dining
A room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.

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 $596 total
includes taxes & fees
Oct 13 - Oct 14
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
A two-story house with a balcony, a staircase, and a view of the beach.
A beach view with a swimming pool, palm trees, and lounge chairs.
A kitchen with a window, a sink, and wooden cabinets.
A beach with palm trees, a wooden dock, 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 $463
CA $1,039 total
includes taxes & fees
Oct 19 - Oct 20
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
An aerial view of a resort with a large pool, palm trees, and a pier.
A modern kitchen with a central island, bar stools, a refrigerator, and a seating area with a sofa and chairs.
An aerial view of a coastal residential area with multiple tennis courts, a marina, and houses with ocean views.
A balcony with wicker furniture, a wooden table, and a view of the surrounding area.

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
CA $499
CA $995 total
includes taxes & fees
Oct 26 - Oct 27
Spanish Queen @Venture Out, Cudjoe Key
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.
Outdoor dining
A marina with RVs and mobile homes, a swimming pool, and a view of the ocean.

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views
Cudjoe Key
CA $262
CA $703 total
includes taxes & fees
Oct 13 - Oct 14
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Top Upper Sugarloaf Sound Hotel Reviews

Sugar Loaf Lodge

Sugar Loaf Lodge

8/10 Good
"Hostess was wonderful. The rooms traditional with the most amazing views of the gulf. coffee and hot tea appreciated. both the tiki and the restaurant were closed but will like to try on next trip south. Definitely nice place to stay on way down to key west."
morgan 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 2 days ago
Private Secluded Ocean View & Pool Near Key West
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

8/10 Good
"Nice for a chill weekend in the lower keys and for people with family accompanying them"
Janey 3-night trip
Posted 3 weeks ago
Sugarloaf Key RV Resort & Cottages
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 3 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
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 6 months ago
Starlight Serenity - Hideaway with Stunning Views

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.
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 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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