Default HTG hotel image

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Oct 19 - Oct 20
Tomorrow
Oct 20 - Oct 21
This weekend
Oct 23 - Oct 25
Next weekend
Oct 30 - Nov 1

Filter by

Star rating

Guest rating

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

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 27 - Oct 28
Sugar Loaf Lodge
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 white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.

2. 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 $341 total
includes taxes & fees
Oct 20 - Oct 21
Old Wooden Bridge Resort and Marina
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 sunset view with a thatched structure and a palm tree by a calm body of water.

3. Parmer's Resort

Parmer's Resort
16 km from Upper Sugarloaf Sound
United States
Mireya
CA $189
CA $259 total
includes taxes & fees
Nov 2 - Nov 3
Parmer's Resort
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 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'.

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

5. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
4.7 km from Upper Sugarloaf Sound
United States
Preetam
CA $732
CA $1,380 total
includes taxes & fees
Oct 20 - Oct 21
Atlantic View Luxury Villa with Pool
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 breakfast setting with a table, chairs, a vase with flowers, and a city view.

6. Hilton Key West Resort & Marina

Hilton Key West Resort & Marina
20.9 km from Upper Sugarloaf Sound
United States
Eric A
CA $167
CA $270 total
includes taxes & fees
Oct 27 - Oct 28
Hilton Key West Resort & Marina
A beachside resort with a wooden deck, palm trees, and a sunset view.
Room
Room
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 27 - Oct 28
Grand Marina Suite by Brightwild Waterfront
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 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.

8. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
21.8 km from Upper Sugarloaf Sound
United States
Jade
CA $138
CA $241 total
includes taxes & fees
Nov 16 - Nov 17
The Perry Hotel & Marina Key West
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 residential building with a covered porch, surrounded by lush greenery and a well-maintained lawn.
A balcony with a view of a swimming pool, palm trees, and a fenced yard.

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 $1,084
CA $2,197 total
includes taxes & fees
Nov 2 - Nov 3
Capmar House by Brightwild Huge Home Pool
A poolside area with lounge chairs, a wooden table, and palm trees.
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.
A large, modern resort with multiple buildings, a central pool, and a marina.

10. 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 2 - Nov 3
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 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.

11. 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
Nov 2 - Nov 3
Mastway House by Brightwild Pool Dock
A poolside area with lounge chairs and umbrellas, a pool, and a view of the ocean.
A modern living room with a sofa, two armchairs, a coffee table, and a dining area with a table and chairs.
A modern resort with a well-maintained lawn, outdoor seating area, and a large building with multiple floors.
A multi-story white building with balconies, a swimming pool, and outdoor seating.

12. New Waterfront Home - Dreamside House

New Waterfront Home - Dreamside House
20.3 km from Upper Sugarloaf Sound
CA $1,807
CA $3,455 total
includes taxes & fees
Oct 25 - Oct 26
New Waterfront Home - Dreamside House
A two-story house with a swimming pool, surrounded by greenery 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.
A two-story house with a covered porch, a front lawn, and palm trees.

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 22 - Oct 23
Seagate House by Brightwild Waterfront w Dock
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 living room with a large dining table, sofas, and a view of a body of water through large windows.

14. New Waterfront Home - Sunray House

New Waterfront Home - Sunray House
20.4 km from Upper Sugarloaf Sound
CA $1,807
CA $3,455 total
includes taxes & fees
Oct 21 - Oct 22
New Waterfront Home - Sunray House
A living room with two sofas, a coffee table, and a view of the outdoors.
A person performing a yoga pose on a mat in a room with a wooden floor and a mirror on the wall.
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.

15. 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 2 - Nov 3
Waterlane House by Brightwild Pool Boat Dock
A two-story house with a pool, surrounded by palm trees and a clear sky.
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.
A two-story house with a front porch, a driveway, and palm trees.

16. 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
Nov 2 - Nov 3
Mirador House by Brightwild Pool Dock
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 modern kitchen with white cabinetry, stainless steel appliances, and a central island with chairs.
A two-story house with a swimming pool, surrounded by lush greenery and a fenced yard.

17. 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
Nov 2 - Nov 3
Spindrift House by Brightwild Huge Pool Dock
A spacious kitchen with modern appliances, a dining area with a wooden table and chairs, and a view of a lake through large windows.
Room
A two-story house with a swimming pool, outdoor seating, and a covered patio.
A covered outdoor area with a pool, white furniture, and a view of a lake.

18. 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
Nov 2 - Nov 3
Springtide House by Brightwild Waterfront 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.
A hotel room with a large bed, a ceiling fan, a window with curtains, a bedside table with a lamp, and a patterned wall.

19. Palmgale House in Key West

Palmgale House in Key West
20.6 km from Upper Sugarloaf Sound
CA $1,449
CA $2,966 total
includes taxes & fees
Oct 25 - Oct 26
Palmgale House in Key West
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 spacious kitchen with a large island, wooden flooring, and pendant lighting.

20. New Altair House by Brightwild Pool Pets

New Altair House by Brightwild Pool Pets
20.5 km from Upper Sugarloaf Sound
CA $1,449
CA $2,966 total
includes taxes & fees
Oct 20 - Oct 21
New Altair House by Brightwild Pool Pets
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
376 reviews
View
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
Looe Key Reef Resort
7.8
Good
1,000 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
A marina with boats docked, a pool area, and a building with a white facade.
Hilton Key West Resort & Marina
9.0
Wonderful
1,797 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 reception area with a wooden sculpture, a reception desk, a computer, and a television.

Sugar Loaf Lodge

Sugar Loaf Lodge
Summerland Key
CA $168
CA $189 total
includes taxes & fees
Oct 27 - Oct 28
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.
Water Views
A spacious living room with a flat-screen TV, a sofa, a dining table, and large windows offering a view of greenery.

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
CA $320
CA $899 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 spacious living area with a large flat-screen TV, a sofa, and a dining area with bar stools.
A two-story house with a balcony and a staircase leading to the upper level.
A modern kitchen with a large island, white cabinetry, and three wicker bar stools.

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
Summerland Key
CA $417
CA $959 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 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 bedroom with a large bed, a ceiling fan, and a balcony with a view of greenery.

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
Summerland Key
CA $732
CA $1,380 total
includes taxes & fees
Oct 20 - Oct 21
Atlantic View Luxury Villa with Pool
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 view with a swimming pool, palm trees, and lounge chairs.
A kitchen with a window, a sink, and wooden cabinets.

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 $460
CA $1,031 total
includes taxes & fees
Oct 20 - Oct 21
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 room with a sliding glass door, a small table with a 'WELCOME' sign, a refrigerator, and a wicker chair.
A resort with a swimming pool, beach area, and marina.
A coastal residential area with houses, a marina, and a flag.

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
Nov 2 - Nov 3
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.
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.

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
CA $495
CA $987 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.
Outdoor dining
A coastal residential area with houses, a marina, and a flag.
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 $282
CA $726 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 1 day 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 3 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 9 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.

Explore a world of travel with Expedia