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Find hotels near Upper Sugarloaf Key, Summerland Key from ￥20,983

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Oct 23 - Oct 24
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Oct 24 - Oct 25
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Oct 23 - Oct 25
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Oct 30 - Nov 1

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Our top choices for Upper Sugarloaf Key hotels

A spacious living area with a kitchen island, a staircase, and large windows offering a view of the outdoors.
A wooden deck with a swing chair and a view of a lake.
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.

1. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
1.2 km from Upper Sugarloaf Key
United States
max
￥45,714
￥105,736 total
includes taxes & fees
Oct 27 - Oct 28
Starlight Serenity - Hideaway w Stunning Views
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.

2. Sugar Loaf Lodge

Sugar Loaf Lodge
4.1 km from Upper Sugarloaf Key
United States
Mariia
￥18,651
￥20,983 total
includes taxes & fees
Oct 26 - Oct 27
Sugar Loaf Lodge
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'.

3. Looe Key Reef Resort

Looe Key Reef Resort
12.2 km from Upper Sugarloaf Key
United States
Stephen
￥21,980
￥24,727 total
includes taxes & fees
Oct 26 - Oct 27
Looe Key Reef Resort
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 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.

4. Parmer's Resort

Parmer's Resort
14.1 km from Upper Sugarloaf Key
United States
Mireya
￥21,018
￥28,760 total
includes taxes & fees
Nov 19 - Nov 20
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 floating houseboat with a covered deck and seating area, docked at a marina.
A row of houseboats docked at a marina with clear reflections in the water.

5. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
18.6 km from Upper Sugarloaf Key
United States
Daisybel
￥13,954
￥37,739 total
includes taxes & fees
Oct 26 - Oct 27
Old Wooden Bridge Resort and Marina
View all properties

Compare top hotels near Upper Sugarloaf Key

A spacious living area with a kitchen island, a staircase, and large windows offering a view of the outdoors.

Starlight Serenity - Hideaway w Stunning Views

1.2 km from Upper Sugarloaf Key
View
A waterfront building with a flat roof, large windows, and a balcony.

Sugar Loaf Lodge

4.1 km from Upper Sugarloaf Key
View
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

Looe Key Reef Resort

12.2 km from Upper Sugarloaf Key
View
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

Parmer's Resort

14.1 km from Upper Sugarloaf Key
View
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

Old Wooden Bridge Resort and Marina

18.6 km from Upper Sugarloaf Key
View
10.0
Exceptional
1 review
8.2
Very good
1,000 reviews
7.8
Good
1,000 reviews
9.0
Wonderful
1,000 reviews
8.6
Excellent
376 reviews
￥45,714
￥105,736 total
includes taxes & fees
Oct 27 - Oct 28
￥18,651
￥20,983 total
includes taxes & fees
Oct 26 - Oct 27
￥21,980
￥24,727 total
includes taxes & fees
Oct 26 - Oct 27
￥21,018
￥28,760 total
includes taxes & fees
Nov 19 - Nov 20
￥13,954
￥37,739 total
includes taxes & fees
Oct 26 - Oct 27

Hotels recommended for families near Upper Sugarloaf Key

A wooden deck with a hanging hammock and a view of a green landscape.
Water Views
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.

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
￥34,951
￥97,840 total
includes taxes & fees
Oct 27 - Oct 28
Starlight Serenity - Hideaway with Stunning Views
A spacious living area with a kitchen island, a staircase, and large windows offering a view of the outdoors.
A wooden deck with a swing chair and a view of a lake.
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
￥45,714
￥105,736 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 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
￥81,108
￥152,960 total
includes taxes & fees
Oct 26 - Oct 27
Atlantic View Luxury Villa with Pool
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 waterfront property with a pool, palm trees, and a house with a balcony.
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
￥50,937
￥114,237 total
includes taxes & fees
Oct 26 - Oct 27
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
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
￥18,651
￥20,983 total
includes taxes & fees
Oct 26 - Oct 27
Sugar Loaf Lodge
An aerial view of a resort with a large pool, palm trees, and a pier.
A bedroom with a large bed, two bedside lamps, a ceiling fan, a window with a view of palm trees, and a wicker basket.
A balcony with wicker furniture, a wooden table, and a view of the surrounding area.
An aerial view of a coastal residential area with multiple tennis courts, a marina, and houses with ocean views.

Spanish Queen @Venture Out, Cudjoe Key

Spanish Queen @Venture Out, Cudjoe Key
Cudjoe Key
￥54,856
￥107,948 total
includes taxes & fees
Oct 26 - Oct 27
Spanish Queen @Venture Out, Cudjoe Key
A coastal property with a dock, white buildings, and a clear view of the ocean.
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
A spacious living area with a sofa, dining table, chairs, and a balcony with a view.
A coastal residential area with houses, a marina, and a flag.

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise

Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
Cudjoe Key
￥58,503
￥113,561 total
includes taxes & fees
Oct 30 - Oct 31
Oceanfront 2BR Retreat - 35' Dock, Sunrise Views, Boater's Paradise
A resort with a pool area, lounge chairs, and a small island with thatched umbrellas.
Outdoor dining
A resort with a swimming pool, beach area, and marina.
A coastal RV park with multiple mobile homes, a marina, and a clear view of the ocean.

Canalfront Coastal Retreat w/Open Water Views & Fishing Dock

Canalfront Coastal Retreat w/Open Water Views & Fishing Dock
Cudjoe Key
￥29,622
￥77,465 total
includes taxes & fees
Oct 27 - Oct 28
Canalfront Coastal Retreat w/Open Water Views & Fishing Dock

Top Upper Sugarloaf Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"Loved it definitely will be hack when we can"
Bryce 3-night trip
Posted 23 hours ago
Sugarloaf Key Hotel at KOA Resort
Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

10/10 Excellent
"Great"
Lori 7-night trip
Posted 2 days ago
Sugarloaf Key RV Resort & Cottages
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 5 days 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 13 days ago
Private Secluded Ocean View & Pool Near Key West
Gorgeous new build on Cudjoe Marina Basin with 80 ft boat dock and private pool

Gorgeous new build on Cudjoe Marina Basin with 80 ft boat dock and private pool

10/10 Excellent
"This is our second year staying here and we’re already booked again for next year. We can’t recommend this place enough. They have thought of everything to make your stay memorable. From the location right across from the marina, so you can watch all the boats, to the pool, to the outdoor kitchen, and all the other great amenities that they provide. You don’t need anything except for your boat and bathing suit. You won’t be disappointed!"
Paul D. 42-night trip
Posted 2 months ago
Gorgeous new build on Cudjoe Marina Basin with 80 ft boat dock and private pool
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!
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 months 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 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

Other attractions near Upper Sugarloaf Key

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 Sound

9.2/10 (17 reviews)
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound 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

Crab Key

Commune with nature and explore the great outdoors at Crab Key during your travels in Summerland Key.
See properties

Frequently asked questions

What's the area like around Upper Sugarloaf Key?
Upper Sugarloaf Key is located in Summerland Key. Travelers like this budget-friendly area for its bars. If you're looking for a convenient place to stay, check out the 19 hotels and other accommodations you'll find within a mile.
What's the best place to stay near Upper Sugarloaf Key?
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 just a short 0.6 mi (0.9 km) from Upper Sugarloaf Key. Other good choices within a short distance include Sugarloaf Key RV Resort & Cottages and Starlight Serenity - Hideaway w Stunning Views.
How many hotels should I expect to find near Upper Sugarloaf Key?
Expedia has 19 hotels and other accommodations within a mile from Upper Sugarloaf Key.
If I need to cancel the hotel reservation for my stay near Upper Sugarloaf Key, will I receive a refund?
Yes! Most hotel room reservations are fully refundable provided that you cancel before the accommodation's cancellation deadline, which in most cases is within 24 or 48 hours of your check-in date. If your reservation is non-refundable, you might be able to still cancel and be given a refund within 24 hours of your booking. Add dates, click "Search", then use the filter option "fully refundable" to view the best deals near Upper Sugarloaf Key.
Where can I learn more about changing or cancelling my trip in the area near Upper Sugarloaf Key?
For additional details about updating your stay near Upper Sugarloaf Key or cancelling it, click here.
What can I see and do near Upper Sugarloaf Key?
Lounge by the water at Florida Keys Beaches and Sugarloaf Beach. Spend some time exploring the great outdoors at Upper Sugarloaf Sound, Venture Out Keys, and Venture Key. Lower Sugarloaf Sound and Out Key are some sights worth a visit in the area.