Top Hotels Near Upper Sugarloaf Key in Summerland Key from NZ$199

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Check prices for these dates

Tonight
5 Nov - 6 Nov
Tomorrow
6 Nov - 7 Nov
This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

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Our top choices for Upper Sugarloaf Key hotels

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

1. Starlight Serenity - Hideaway w Stunning Views

Starlight Serenity - Hideaway w Stunning Views
2.0 star property
1.2 km from Upper Sugarloaf Key
10.0 out of 10, Exceptional, (1 review)
"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."
United States
max
The price is NZ$1,292
includes taxes & fees
12 Nov - 13 Nov
Starlight Serenity - Hideaway w Stunning Views
A waterfront building with a flat roof, large windows, and a balcony.

2. Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
4.1 km from Upper Sugarloaf Key
8.2 out of 10, Very good, (1,000 reviews)
"Very cute place, like at home, the lady on the desk is very sweet and helpful. Good price and close to Kea West."
United States
Mariia
The price is NZ$199
includes taxes & fees
30 Nov - 1 Dec
Sugar Loaf Lodge
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

3. Parmer's Resort

Parmer's Resort
2.5 star property
14.1 km from Upper Sugarloaf Key
9.0 out of 10, Wonderful, (1,002 reviews)
"Super cute place and nice people! Would definitely stay again."
United States
Natalie
The price is NZ$364
includes taxes & fees
18 Nov - 19 Nov
Parmer's Resort
A cozy room with a brown leather sofa, a white table, and a ceiling fan.

4. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
18.6 km from Upper Sugarloaf Key
8.6 out of 10, Excellent, (380 reviews)
"Great view , clean room and excellent staff ( Mr. shaggy )"
United States
Jordan
The price is NZ$485
includes taxes & fees
8 Nov - 9 Nov
Old Wooden Bridge Resort and Marina
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

5. Looe Key Reef Resort

Looe Key Reef Resort
2.5 star property
12.2 km from Upper Sugarloaf Key
7.8 out of 10, Good, (1,000 reviews)
"Everything was amazing staff was very accommodating would definitely recommend"
United States
Stephen
The price is NZ$324
includes taxes & fees
9 Nov - 10 Nov
Looe Key Reef Resort
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Compare popular hotels close to Upper Sugarloaf Key

Property
Property class
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
A wooden deck with a hanging hammock and a view of a green landscape.
Starlight Serenity - Hideaway w Stunning Views
2.0 star property
10.0
Exceptional
1 review
View
A waterfront building with a flat roof, large windows, and a balcony.
Sugar Loaf Lodge
2.5 star property
8.2
Very good
1,000 reviews
View
A white building with a covered patio area, surrounded by palm trees and a view of the ocean.
Parmer's Resort
2.5 star property
9.0
Wonderful
1,002 reviews
View
A cozy room with a brown leather sofa, a white table, and a ceiling fan.
Old Wooden Bridge Resort and Marina
2.5 star property
8.6
Excellent
380 reviews
View
A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.
Looe Key Reef Resort
2.5 star property
7.8
Good
1,000 reviews
View

Hotels recommended for families near Upper Sugarloaf Key

A waterfront building with a flat roof, large windows, and a balcony.

Sugar Loaf Lodge

Sugar Loaf Lodge
2.5 star property
Summerland Key
8.2 out of 10, Very good, (1,000)
The price is NZ$199
includes taxes & fees
30 Nov - 1 Dec
Sugar Loaf Lodge

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 holiday like spending a care-free day in Florida Keys Beaches, a popular beach in Long Beach Estates.
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Top Upper Sugarloaf Key Hotel Reviews

A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.
Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
Old Town Key West

10/10 Excellent

there was nothing at all to dislike. The staff were very cheerful very helpful. The location was excellent. The room was clean and spacious. If I ever returned to Key West, I would have no hesitation at all booking this hotel again.
Australia
Robyn
Reviewed August 6, 2026
Almond Tree Inn Hotel - Adults Only

Frequently Asked Questions

What's the area like around Upper Sugarloaf Key?

Upper Sugarloaf Key is located in Summerland Key. Travellers like this budget-friendly area for its bars. If you're looking for a convenient place to stay, take a look at the 19 hotels and other accommodation options 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 traveller 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 are there near Upper Sugarloaf Key?

Expedia has 19 hotels and other accommodation options 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, you'll find most hotel reservations are fully refundable if you cancel before the hotel’s cancellation deadline, which often is within 24-48 hours of your check-in date. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of your booking. Add your dates and click on "Search", then you can filter by "fully refundable" to review the best deals available 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.