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Find hotels near Upper Sugarloaf Sound, Summerland Key from ￥16,703

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Aug 21 - Aug 22
Tomorrow
Aug 22 - Aug 23
This weekend
Aug 21 - Aug 23
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Aug 28 - Aug 30

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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 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.

1. Sugar Loaf Lodge

Sugar Loaf Lodge
2.2 km from Upper Sugarloaf Sound
United States
Marjorie
￥18,829
￥21,183 total
includes taxes & fees
Aug 24 - Aug 25
Sugar Loaf Lodge
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
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.
A sunset view with a thatched structure and a palm tree by a calm body of water.

2. Parmer's Resort

Parmer's Resort
16 km from Upper Sugarloaf Sound
United States
John
￥16,079
￥23,276 total
includes taxes & fees
Aug 23 - Aug 24
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 white building with a sloped roof, a balcony with blue chairs, and a yellow bird sculpture on the roof.
A floating houseboat with a covered deck and seating area, docked at a marina.

3. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
20.5 km from Upper Sugarloaf Sound
United States
Lisa
￥14,239
￥38,271 total
includes taxes & fees
Sep 1 - Sep 2
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 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.

4. Looe Key Reef Resort

Looe Key Reef Resort
14 km from Upper Sugarloaf Sound
United States
Elizabeth
￥14,847
￥16,703 total
includes taxes & fees
Sep 2 - Sep 3
Looe Key Reef Resort
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 marina with numerous yachts docked, surrounded by palm trees and a clear sky.
A marina with boats docked, a building with multiple floors, and palm trees in the background.

5. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
21.8 km from Upper Sugarloaf Sound
United States
Boyan
￥22,546
￥35,171 total
includes taxes & fees
Aug 26 - Aug 27
The Perry Hotel & Marina Key West
A marina with numerous boats docked, a swimming pool, and palm trees.
A hotel room with a balcony overlooking a marina and the ocean.
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
Linda
￥21,279
￥33,434 total
includes taxes & fees
Aug 27 - Aug 28
Hilton Key West Resort & Marina
A modern house with a swimming pool, outdoor seating, and palm trees.
A covered outdoor seating area with white chairs and a ceiling fan, overlooking a swimming pool and a well-maintained lawn.
A modern kitchen with a central island, bar stools, pendant lights, and a staircase leading to another room.
A dining area with a wooden table and chairs, large windows, and a view of the outdoors.

7. Floralee House in Key West

Floralee House in Key West
20.6 km from Upper Sugarloaf Sound
￥162,870
￥333,445 total
includes taxes & fees
Aug 23 - Aug 24
Floralee House in Key West
A spacious kitchen with a large island, pendant lighting, and a dining area with a table and chairs.
A modern kitchen with a central island, bar stools, pendant lights, and a dining area with a sofa and chairs.
A modern kitchen with a central island, bar stools, pendant lights, and a view of the outdoors.
A modern kitchen with white cabinetry, a central island, and pendant lighting.

8. New Windrose House by Brightwild Pool

New Windrose House by Brightwild Pool
20.6 km from Upper Sugarloaf Sound
￥154,727
￥324,284 total
includes taxes & fees
Sep 21 - Sep 22
New Windrose House by Brightwild Pool
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 a large island, pendant lighting, and a backsplash with blue tiles.
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.

9. Ebberly House by Brightwild Amazing Pool

Ebberly House by Brightwild Amazing Pool
20.6 km from Upper Sugarloaf Sound
￥154,727
￥324,284 total
includes taxes & fees
Sep 21 - Sep 22
Ebberly House by Brightwild Amazing Pool
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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
1,001 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
1,006 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
366 reviews
View
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
Looe Key Reef Resort
7.6
Good
1,002 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
1,333 reviews
View

Top Upper Sugarloaf Sound Hotel Reviews

Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

10/10 Excellent
"We had an amazing stay AGAIN at Sugarloaf RV & Cottage Resort in the Florida Keys! The property was beautiful, peaceful, clean, and the perfect place to relax and enjoy the Keys. The location is fantastic—close enough to Key West while still giving you that quiet, laid-back island feeling. The staff was friendly and welcoming, and everything was well maintained. We especially loved the tropical atmosphere and being able to truly disconnect and enjoy paradise. 🌴☀️🌊 We’ll definitely be back and highly recommend Sugarloaf to anyone looking for a relaxing Florida Keys getaway!"
Osmany 3-night trip
Posted 3 days ago
Sugarloaf Key RV Resort & Cottages
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"Property was very well maintained, amenities were great, staff was knowledgeable and friendly."
Andres 3-night trip
Posted 3 days ago
Sugarloaf Key Hotel at KOA Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

10/10 Excellent
"Excellent place to Stay. calm and relaxed environment"
Ashish 1-night trip
Posted 4 days ago
Sugar Loaf Lodge
Private Pool Oasis — 3 King Suites | 30 Min to Key West

Private Pool Oasis — 3 King Suites | 30 Min to Key West

10/10 Excellent
"Very clean and a great area! Thank you!!!"
Daniel P. 5-night trip
Posted 3 weeks ago
Private Pool Oasis — 3 King Suites | 30 Min to Key West
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 weeks ago
Oceanside, pet friendly, smart home with plenty of paddle equipment
Florida Keys Beach Getaway

Florida Keys Beach Getaway

10/10 Excellent
"Man, this place was awesome. If it wasnt for the sea weed, we would never want or have a need to leave. Seaweed was thinning out towards the end of our trip, but man, this place was worth it. Tom, your a gem bud."
Justin R. 7-night trip
Posted 3 weeks ago
Florida Keys Beach Getaway
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 2 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 2 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 4 months ago
Starlight Serenity - Hideaway with Stunning Views

Other attractions near Upper Sugarloaf Sound

A beach with a pier extending into the ocean during sunset.

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?
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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.
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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 439 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 RV Resort & Cottages is one of the top choices for your stay based on our traveler data, and this vacation home offers an outdoor pool and free parking. It's located 1.5 mi (2.3 km) from Upper Sugarloaf Sound. Other good options within a few miles include Sugarloaf Key Hotel at KOA Resort and Sugar Loaf Lodge.
How many hotels will I find close to Upper Sugarloaf Sound?
Expedia has 439 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.
Where can I learn more about changing or cancelling my trip in the area near Upper Sugarloaf Sound?
For additional details about updating your stay near Upper Sugarloaf Sound or cancelling it, head over to our customer service page.
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, Venture Out Keys, and Lower Sugarloaf Sound, you can surround yourself with nature. Venture Key and Out Key are both worth a visit while you're checking out the area.