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Find hotels near Upper Sugarloaf Key, Summerland Key from CA $111

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Check prices for these dates

Tonight
Sep 25 - Sep 26
Tomorrow
Sep 26 - Sep 27
This weekend
Sep 25 - Sep 27
Next weekend
Oct 2 - Oct 4

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Our top choices for Upper Sugarloaf Key hotels

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 two-story house with a balcony and a staircase leading to the upper level.
A spacious living area with a large flat-screen TV, a sofa, and a dining area with bar stools.

1. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
1.2 km from Upper Sugarloaf Key
United States
max
CA $327
CA $884 total
includes taxes & fees
Oct 5 - Oct 6
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 concrete pathway flanked by lush green foliage, leading to a shaded area.
A large house with a pool, surrounded by lush greenery.

2. Atlantic View Luxury Villa with Pool

Atlantic View Luxury Villa with Pool
2.7 km from Upper Sugarloaf Key
United States
Preetam
CA $732
CA $1,380 total
includes taxes & fees
Oct 3 - Oct 4
Atlantic View Luxury Villa with Pool
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 swimming pool with a surrounding deck, palm trees, and lounge chairs.
A reception area with a wooden sculpture, a reception desk, a computer, and a television.

3. Sugar Loaf Lodge

Sugar Loaf Lodge
4.1 km from Upper Sugarloaf Key
United States
Kevin
CA $140
CA $158 total
includes taxes & fees
Sep 27 - Sep 28
Sugar Loaf Lodge
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 dining area with a table and chairs, a ceiling fan, a television, and a window with a view of the outdoors.
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
CA $203
CA $275 total
includes taxes & fees
Oct 4 - Oct 5
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 thatched-roof building with a sign for 'Look Reef Resort' and 'Tiki Bar'.
A sign for Looe Key Reef Resort's tiki bar, surrounded by palm trees and a thatched-roof structure.

5. Looe Key Reef Resort

Looe Key Reef Resort
12.2 km from Upper Sugarloaf Key
United States
Michel
CA $98
CA $111 total
includes taxes & fees
Oct 5 - Oct 6
Looe Key Reef 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 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.

6. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
18.6 km from Upper Sugarloaf Key
United States
abhimanyu
CA $127
CA $342 total
includes taxes & fees
Sep 27 - Sep 28
Old Wooden Bridge Resort and Marina
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Compare popular hotels close to Upper Sugarloaf Key

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A wooden deck with a railing, wicker chairs, and a view of greenery.
Starlight Serenity - Hideaway w Stunning Views
10.0
Exceptional
1 review
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 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
1,003 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
1,003 reviews
View

Top Upper Sugarloaf Key Hotel Reviews

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 days ago
Sugarloaf Key RV Resort & Cottages
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"Extraordinarily clean and well maintained. We stayed in the hotel which was well thought out"
Patrick 4-night trip
Posted 7 days ago
Sugarloaf Key Hotel at KOA Resort
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 11 days ago
Private Secluded Ocean View & Pool Near Key West
Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot

Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot

10/10 Excellent
"Hard to beat the view."
Kevin K. 28-night trip
Posted 1 month ago
Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot
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 1 month 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 2 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 2 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 3 months ago
Starlight Serenity - Hideaway w Stunning Views

Other attractions near Upper Sugarloaf Key

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 Sound

9.2/10 (17 reviews)
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
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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.
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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.
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.

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