The Best Hotels Closest to Upper Sugarloaf Sound in Summerland Key - 2026 Updated Prices

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Our top choices for Upper Sugarloaf Sound hotels

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

1. Sugar Loaf Lodge

2.2 km from Upper Sugarloaf Sound

David

₹10,462 total

includes taxes & fees

30 Nov - 1 Dec

A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.

2. The Perry Hotel & Marina Key West

21.8 km from Upper Sugarloaf Sound

Dharmesh Raju

₹17,713 total

includes taxes & fees

30 Nov - 1 Dec

A marina with boats docked, a pool area, and a building with a white facade.

3. Hilton Key West Resort & Marina

20.9 km from Upper Sugarloaf Sound

Kevin

₹17,974 total

includes taxes & fees

17 Nov - 18 Nov

A white building with a covered patio area, surrounded by palm trees and a view of the ocean.

4. Parmer's Resort

16 km from Upper Sugarloaf Sound

Natalie

₹19,139 total

includes taxes & fees

1 Dec - 2 Dec

A cozy room with a brown leather sofa, a white table, and a ceiling fan.

5. Old Wooden Bridge Resort and Marina

20.5 km from Upper Sugarloaf Sound

Anthony

₹20,596 total

includes taxes & fees

4 Dec - 5 Dec

A rustic wooden structure with a thatched roof, multiple tables and chairs, and flags hanging from the ceiling.

6. Looe Key Reef Resort

14 km from Upper Sugarloaf Sound

Stephen

₹17,434 total

includes taxes & fees

20 Nov - 21 Nov

A two-story house with a pool, surrounded by palm trees and a clear sky.

7. Mirador House by Brightwild Pool Dock

20.5 km from Upper Sugarloaf Sound

₹173,324 total

includes taxes & fees

25 Nov - 26 Nov

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Compare popular hotels close to Upper Sugarloaf Sound

Property	Property class	Guest rating
Sugar Loaf Lodge	2.5 star property	8.2 Very good 1,001 reviews	View
The Perry Hotel & Marina Key West	4.0 star property	9.4 Exceptional 1,315 reviews	View
Hilton Key West Resort & Marina	4.0 star property	9.0 Wonderful 1,791 reviews	View
Parmer's Resort	2.5 star property	9.0 Wonderful 1,003 reviews	View
Old Wooden Bridge Resort and Marina	2.5 star property	8.6 Excellent 382 reviews	View

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 holiday like spending a care-free day in Florida Keys Beaches, a popular beach in Long Beach Estates.

See properties

Top Upper Sugarloaf Sound Hotel Reviews

Sugar Loaf Lodge

Summerland Key

10/10 Excellent

Malcolm

The Perry Hotel & Marina Key West

Stock Island

10/10 Excellent

lovely welcome on arrival by a chap named Chris on the desk. helped us with everything very friendly and informative! lovely hotel perfect for what we needed a weeks peace after orlando and the shuttle allowed us to dip in and out of all the fun. pool area lovely and our room too , overlooked the pool very clean and comfortable housekeeping great . matt’s kitchen offered a great breakfast again with lovely staff one guy in particular lovely with all his recs . telling us all about henry &...

Julie

A pool area with lounge chairs and a table, surrounded by palm trees.

Orchid Key Inn - Adults Only

Old Town Key West

10/10 Excellent

Lisa

A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.

Alexander's Guesthouse - Adult Exclusive

Old Town Key West

10/10 Excellent

David

A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.

Artist House Key West

Key West Historic District

10/10 Excellent

This property is truly amazing but what adds the extra star are the staff, Shawn made our holiday, could not do enough for us. The house is just beautiful and so much history and extremely central. Just a few things that would advise but doesn’t effect the overall place, 1) the room we were in was opposite checkin so can be a bit noisy at times 2) the light from the outside garden pool area is on all night and keeps the room very light at night. These didn’t bother us but may affect others

shaun

A tropical outdoor area with palm trees, hanging plants, and string lights.

Douglas House - Adults Only

Old Town Key West

10/10 Excellent

The douglas house was very very nice! The staff was friendly and knowledgeable. The only 1 thing I could say we were taken aback about was , the place is adult only which we like because our kids are grown and we dont really want to have to deal with , listen to , or share spaces with other people's children , but there were several guests that were very very comfortable in their bodies and were very rude in and around the pool most of the time . We dont consider ourselves prudes at all but the...

Ron

A hammock in a garden with a wooden pergola, palm trees, and a view of the ocean.

Hyatt Vacation Club at Windward Pointe, Key West

Key West

10/10 Excellent

Claire

A modern interior with a staircase, a sofa set, a wooden table, and a television.

Simonton Court Historic Inn & Cottages

Key West Historic District

10/10 Excellent

Lee

A two-story house with a covered porch, a brick pathway, and a large tree.

The Marquesa Hotel

Old Town Key West

10/10 Excellent

maria

A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.

Key West Villas

Old Town Key West

10/10 Excellent

julie

A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

Island City House Hotel

Key West Historic District

10/10 Excellent

We stayed here for a single night, having driven down from Miami on the Overseas Highway. The hotel is in a great quiet area just a couple of blocks' walk from the main part of the old town. There is occasionally on-street parking available outside, you just have to be lucky but we parked overnight in a nearby outdoor car park at an old church for $15 (cash only) The hotel is in great condition, and the rooms were spotlessly clean. We stayed in the Cigar Suite on the first floor with a balcony...

Mark

A pool area with lounge chairs and palm trees.

Santa Maria Suites

Old Town Key West

10/10 Excellent

Tim

A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

The Grand Guesthouse

Old Town Key West

10/10 Excellent

This property is a gem. Very friendly and welcoming host who couldn't do enough to ensure we were welcome and enjoyed our staff. The room was spotlessly clean, the free continental breakfast and free water, tea and coffee and sun supplies were the icing on the cake. Within easy walking distance of everything the historic old town has to offer. Cant recommend this highly enough and will definitely recommend to all our friends and family

Andrea

Hilton Key West Resort & Marina

Stock Island

10/10 Excellent

The Oceans Edge is an incredible resort. I was a little wary of staying on Stock Island instead of downtown Key West itself, however when I saw the tropical gates of the hotel all of my concerns were blown away. Everything about this hotel is stunning, from the luscious tropical grounds to the beautifully appointed rooms. We were In block 1, which had incredible tropical views from the balcony through the marina out to the ocean. Our room felt luxurious and tranquil, with comfortable beds and...

Brittany

Frequently Asked Questions

What's the area like around Upper Sugarloaf Sound?

Upper Sugarloaf Sound is located in Summerland Key. Travellers 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 traveller 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 can I expect to find close to Upper Sugarloaf Sound?

Expedia has 446 hotels and other accommodation options 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 reservations are fully refundable provided that you cancel prior to the accommodation's cancellation deadline, which often is within 24-48 hours of your arrival date. If you have a reservation that's non-refundable, it might still be possible to cancel it and be given a refund within 24 hours of your booking. Enter dates in and click on "Search", then filter by "fully refundable" to review the best deals available 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 out exploring.

Search Hotels Near Upper Sugarloaf Sound, Summerland Key

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Treat yourself

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Check prices for these dates

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Our top choices for Upper Sugarloaf Sound hotels

1. Sugar Loaf Lodge

2. The Perry Hotel & Marina Key West

3. Hilton Key West Resort & Marina

4. Parmer's Resort

5. Old Wooden Bridge Resort and Marina

6. Looe Key Reef Resort

7. Mirador House by Brightwild Pool Dock

Compare popular hotels close to Upper Sugarloaf Sound

Other attractions near Upper Sugarloaf Sound

Florida Keys Beaches

Top Upper Sugarloaf Sound Hotel Reviews

Sugar Loaf Lodge

10/10 Excellent

Frequently Asked Questions

What's the area like around Upper Sugarloaf Sound?

Where is the best place to stay close to Upper Sugarloaf Sound?

How many hotels can I expect to find close to Upper Sugarloaf Sound?

If I need to cancel the hotel reservation for my stay near Upper Sugarloaf Sound, will I receive a refund?

What can I see and do near Upper Sugarloaf Sound?