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Find hotels near Upper Sugarloaf Sound, Summerland Key from CA $189

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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 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
Mariia
CA $168
CA $189 total
includes taxes & fees
Oct 26 - Oct 27
Sugar Loaf Lodge
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A marina with boats docked, a swimming pool, and palm trees.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.
A hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.

2. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
21.8 km from Upper Sugarloaf Sound
United States
Jade
CA $135
CA $235 total
includes taxes & fees
Nov 16 - Nov 17
The Perry Hotel & Marina Key West
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
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.
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

Parmer's Resort
16 km from Upper Sugarloaf Sound
United States
Mireya
CA $184
CA $253 total
includes taxes & fees
Nov 15 - Nov 16
Parmer's Resort
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 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.

4. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
20.5 km from Upper Sugarloaf Sound
United States
Daisybel
CA $126
CA $340 total
includes taxes & fees
Oct 25 - Oct 26
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 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.
A thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.

5. Looe Key Reef Resort

Looe Key Reef Resort
14 km from Upper Sugarloaf Sound
United States
Stephen
CA $198
CA $223 total
includes taxes & fees
Oct 26 - Oct 27
Looe Key Reef Resort
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.

6. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
4.7 km from Upper Sugarloaf Sound
United States
Preetam
CA $730
CA $1,377 total
includes taxes & fees
Oct 21 - Oct 22
Atlantic View Luxury Villa with Pool
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.

7. Grand Marina Suite by Brightwild Waterfront

Grand Marina Suite by Brightwild Waterfront
20.5 km from Upper Sugarloaf Sound
United States
Pawel
CA $458
CA $858 total
includes taxes & fees
Oct 26 - Oct 27
Grand Marina Suite by Brightwild Waterfront
A white two-story house with a balcony and a swimming pool.
A spacious living area with a wooden dining table, comfortable seating, a flat-screen TV, and a ceiling fan.
A spacious kitchen with wooden cabinets, a large island, and modern appliances.
A balcony with a view of a swimming pool, palm trees, and a fenced yard.

8. Capmar House by Brightwild Huge Home Pool

Capmar House by Brightwild Huge Home Pool
20.5 km from Upper Sugarloaf Sound
France
Karen
CA $1,084
CA $2,197 total
includes taxes & fees
Oct 25 - Oct 26
Capmar House by Brightwild Huge Home Pool
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.
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 modern house with a swimming pool, lounge chairs, and a covered patio area.

9. Palmgale House in Key West

Palmgale House in Key West
20.6 km from Upper Sugarloaf Sound
CA $1,445
CA $2,959 total
includes taxes & fees
Oct 25 - Oct 26
Palmgale House in Key West
A modern kitchen with a central island, bar stools, and a large window.
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.
A modern two-story house with a paved driveway and a well-maintained lawn.

10. Brand New Catchlight House With Private Pool

Brand New Catchlight House With Private Pool
20.6 km from Upper Sugarloaf Sound
CA $1,380
CA $2,885 total
includes taxes & fees
Oct 21 - Oct 22
Brand New Catchlight House With Private Pool
A poolside area with lounge chairs, a wooden table, and palm trees.
A large, modern resort with multiple buildings, a central pool, and a marina.
A patio with white wicker furniture, palm trees, and a view of a lake.
A modern living room with a sectional sofa, a coffee table, and a view of the outdoor patio area.

11. The Fairhaven House at Solaire Lunara Bay

The Fairhaven House at Solaire Lunara Bay
20.2 km from Upper Sugarloaf Sound
CA $1,807
CA $3,455 total
includes taxes & fees
Nov 1 - Nov 2
The Fairhaven 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 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.
A two-story house with a swimming pool, a covered patio, and a staircase leading to the upper floor.

12. Mastway House by Brightwild Pool Dock

Mastway House by Brightwild Pool Dock
20.3 km from Upper Sugarloaf Sound
CA $1,084
CA $2,197 total
includes taxes & fees
Oct 25 - Oct 26
Mastway House by Brightwild Pool Dock
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.

13. Seagate House by Brightwild Waterfront w Dock

Seagate House by Brightwild Waterfront w Dock
20.5 km from Upper Sugarloaf Sound
CA $1,084
CA $2,197 total
includes taxes & fees
Oct 21 - Oct 22
Seagate House by Brightwild Waterfront w Dock
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 front porch, a double door, and a number '8' on the door.
A two-story house with a swimming pool, white railings, and a covered patio area.

14. Waterlane House by Brightwild Pool Boat Dock

Waterlane House by Brightwild Pool Boat Dock
20.5 km from Upper Sugarloaf Sound
CA $1,084
CA $2,197 total
includes taxes & fees
Nov 1 - Nov 2
Waterlane House by Brightwild Pool Boat 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 living room with a sofa, coffee table, and a rug. There is a kitchen area with a bar and seating.

15. Mirador House by Brightwild Pool Dock

Mirador House by Brightwild Pool Dock
20.5 km from Upper Sugarloaf Sound
CA $1,084
CA $2,437 total
includes taxes & fees
Oct 21 - Oct 22
Mirador House by Brightwild Pool Dock
A modern kitchen with white cabinetry, a marble countertop, and a central island with bar stools.
Room
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.

16. New Altair House by Brightwild Pool Pets

New Altair House by Brightwild Pool Pets
20.5 km from Upper Sugarloaf Sound
CA $1,445
CA $2,959 total
includes taxes & fees
Oct 21 - Oct 22
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 spacious living area with a large dining table, white sofas, and a TV mounted on the wall.
A two-story white house with a swimming pool, outdoor seating area, and a well-maintained lawn.
A spacious dining area with a long wooden table, six chairs, and pendant lights.

17. Brand New Build Larkshine House - Pool

Brand New Build Larkshine House - Pool
20.6 km from Upper Sugarloaf Sound
CA $1,807
CA $3,366 total
includes taxes & fees
Oct 21 - Oct 22
Brand New Build Larkshine House - Pool
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, outdoor seating, and a fenced yard.
A spacious interior with a wooden staircase, a modern light fixture, and a view of the outdoors.
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with chairs.

18. Spindrift House by Brightwild Huge Pool Dock

Spindrift House by Brightwild Huge Pool Dock
20.5 km from Upper Sugarloaf Sound
CA $1,084
CA $2,197 total
includes taxes & fees
Oct 21 - Oct 22
Spindrift House by Brightwild Huge Pool Dock
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 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.

19. Ebberly House by Brightwild Amazing Pool

Ebberly House by Brightwild Amazing Pool
20.6 km from Upper Sugarloaf Sound
CA $1,445
CA $2,959 total
includes taxes & fees
Oct 25 - Oct 26
Ebberly House by Brightwild Amazing Pool
A spacious kitchen with modern appliances, a dining area with a wooden table and chairs, and a view of a lake through large windows.
A two-story house with a swimming pool, outdoor seating, and a covered patio.
Room
A modern kitchen with a sliding glass door leading to a balcony, a dining area with a gray sofa, and a small island with a vase of white flowers.

20. Springtide House by Brightwild Waterfront Pool

Springtide House by Brightwild Waterfront Pool
20.4 km from Upper Sugarloaf Sound
CA $1,084
CA $2,197 total
includes taxes & fees
Oct 21 - Oct 22
Springtide House by Brightwild Waterfront 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
1,001 reviews
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
1,311 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
A marina with boats docked, a pool area, and a building with a white facade.
Hilton Key West Resort & Marina
9.0
Wonderful
1,798 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
376 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 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.

Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
CA $168
CA $189 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 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 $315
CA $891 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 modern kitchen with a large island, white cabinetry, and three wicker bar stools.
A spacious living room with a large flat-screen TV, a white sofa, two round coffee tables, and a dining area with a glass table and wicker chairs.
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 $411
CA $952 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 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.

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
Summerland Key
CA $730
CA $1,377 total
includes taxes & fees
Oct 21 - Oct 22
Atlantic View Luxury Villa with Pool
A two-story house with a balcony, a staircase, and a view of the beach.
A kitchen with a window, a sink, and wooden cabinets.
A waterfront property with a pool, palm trees, and a house with a balcony.
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 $458
CA $1,028 total
includes taxes & fees
Oct 21 - Oct 22
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 resort with a swimming pool, beach area, and marina.
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 $176
CA $590 total
includes taxes & fees
Oct 27 - Oct 28
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.
An aerial view of a coastal residential area with multiple tennis courts, a marina, and houses with ocean views.
A modern kitchen with a central island, bar stools, a refrigerator, and a seating area with a sofa and chairs.
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 $494
CA $984 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 coastal residential area with houses, a marina, and a flag.
Outdoor dining
A marina with boats docked, a clear sky, and a calm waterway.

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 $281
CA $724 total
includes taxes & fees
Oct 21 - Oct 22
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option

Top Upper Sugarloaf Sound Hotel Reviews

Sugar Loaf Lodge

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."
Mariia 1-night trip
Posted 2 days ago
Sugar Loaf Lodge
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

10/10 Excellent
"Newly updated property with new bungalows. Very clean and nice. Views are beautiful! Staff was very attentive. We would stay again when we are in the area."
Terri 4-night trip
Posted 4 days ago
Sugarloaf Key RV Resort & Cottages
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 10 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
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
Waterfront home with a large dock, pool, and deck area. Can accommodate pets.

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."
Denise F. 30-night trip
Posted 7 months ago
Waterfront home with a large dock, pool, and deck area. Can accommodate pets.

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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