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Find hotels near Upper Sugarloaf Sound, Summerland Key from CA $161

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Oct 10 - Oct 11
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Oct 11 - Oct 12
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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 swimming pool with a surrounding deck, palm trees, and lounge chairs.
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
Richard
CA $169
CA $190 total
includes taxes & fees
Oct 13 - Oct 14
Sugar Loaf Lodge
A cozy room with a brown leather sofa, a white table, and a ceiling fan.
A white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.
A compact kitchen with wooden beams, a dining area with white chairs, and a TV mounted on the wall.
A floating houseboat with a covered deck and seating area, docked at a marina.

2. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
20.5 km from Upper Sugarloaf Sound
United States
Daisybel
CA $125
CA $340 total
includes taxes & fees
Oct 12 - Oct 13
Old Wooden Bridge Resort and Marina
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
A sunset view with a thatched structure and a palm tree by a calm body of water.
A spacious living area with a flat-screen TV, a wooden coffee table, a sofa with colorful cushions, and a blue chair.
Beach chairs and a blue umbrella on a sandy shore with a calm body of water and a palm tree in the background.

3. Parmer's Resort

Parmer's Resort
16 km from Upper Sugarloaf Sound
United States
Mireya
CA $209
CA $281 total
includes taxes & fees
Nov 3 - Nov 4
Parmer's Resort
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 breakfast setting with a table, chairs, a vase with flowers, and a city view.
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 $189
CA $296 total
includes taxes & fees
Oct 15 - Oct 16
Hilton Key West Resort & Marina
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 balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.
A restaurant with wooden tables and chairs, a counter with seafood signs, and large windows.

5. 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 26 - Oct 27
The Perry Hotel & Marina Key West
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'.

6. Looe Key Reef Resort

Looe Key Reef Resort
14 km from Upper Sugarloaf Sound
United States
Stephen
CA $144
CA $161 total
includes taxes & fees
Oct 14 - Oct 15
Looe Key Reef Resort
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
1,000 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
373 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
1,001 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
1,800 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
1,315 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 swimming pool with a surrounding deck, palm trees, and lounge chairs.
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 $169
CA $190 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 area with a kitchen island, a staircase, and large windows offering a view of the outdoors.
Water Views

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
CA $294
CA $870 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 two-story house with a balcony and a staircase leading to the upper level.

Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
Summerland Key
CA $408
CA $979 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 large house with a pool, surrounded by lush greenery.
A bedroom with a large bed, a ceiling fan, and a balcony with a view of greenery.
A concrete pathway flanked by lush green foliage, leading to a shaded area.

Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
Summerland Key
CA $736
CA $1,388 total
includes taxes & fees
Oct 11 - Oct 12
Atlantic View Luxury Villa with Pool
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
Outdoor dining
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.

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 11 - Oct 12
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 with palm trees, a wooden dock, and lounge chairs.
A beach view with a swimming pool, palm trees, and lounge chairs.
A waterfront property with a pool, palm trees, and a house with a balcony.

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 $1,023 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 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 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 $498
CA $992 total
includes taxes & fees
Oct 12 - Oct 13
Spanish Queen @Venture Out, Cudjoe Key
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A marina with RVs and mobile homes, a swimming pool, and a view of the ocean.
A coastal residential area with houses, a marina, and a flag.
A resort with a swimming pool, beach area, and marina.

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 $261
CA $702 total
includes taxes & fees
Oct 11 - Oct 12
Little Piece of Paradise #233 Waterfront Cottage with Dock, Pool & Canal Views

Top Upper Sugarloaf Sound Hotel Reviews

Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Very accommodating! Staff is very friendly! Been coming to Sugarloaf Lodge for many years! Thanks again!"
Richard 2-night trip
Posted 2 weeks ago
Sugar Loaf Lodge
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 2 weeks 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
"Great host ! Few snags but it all worked out great."
Nick N. 3-night trip
Posted 1 month 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 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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