Summerland Key, FL

Travel Guide

Sugarloaf Shores showing a house, a sunset and a bay or harbor
Sugarloaf Shores which includes a bay or harbor and a house
Sugarloaf Shores featuring a sunset and tropical scenes
Sugarloaf Shores showing a house, a sunset and a bay or harbor
Sugarloaf Shores which includes a bay or harbor and a house

Where to stay in Summerland Key

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Cutthroat Harbor Estates

While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Upper Sugarloaf Key are some notable places to visit nearby.

Cutthroat Harbor Estates
Sugarloaf Shores featuring a bay or harbor

Sugarloaf Shores

While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.

Sugarloaf Shores
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Cudjoe Gardens

When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Venture Out Keys, some noteworthy sights in the nearby area.

Cudjoe Gardens
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Breezeswept Beach Estates

While Breezeswept Beach Estates isn't home to many top sights, Newfound Harbor Keys and Cook Island are some notable places to visit nearby.

Breezeswept Beach Estates
Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue, Summerland Key, FL
The price is ￥17,906 per night from Aug 26 to Aug 27
￥17,906
￥24,989 total
Aug 26 - Aug 27
includes taxes & fees
Book a stay at this beach motel in Summerland Key. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in ...
8.8/10 Excellent! (1,003 reviews)
"Sarah was AWESOME"

Reviewed on Jul 29, 2025

Parmer's Resort
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939, Summerland Key, FL
Stay at this 3-star hotel in Summerland Key. Enjoy free WiFi, free parking, and a private beach. Our guests praise the helpful staff and the clean rooms in our ...
9.6/10 Exceptional! (420 reviews)
"We stayed for July 4th and it was perfect! Loved the suite and as a family it was very convenient to have a kitchen, washer and dryer!"

Reviewed on Jul 29, 2025

Get rates
Sugarloaf Key Hotel at KOA Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy, Summerland Key, FL
The price is ￥14,700 per night from Aug 10 to Aug 11
￥14,700
￥16,538 total
Aug 10 - Aug 11
includes taxes & fees
Stay at this hotel in Summerland Key. Enjoy free WiFi, free parking, and a marina. Our guests praise the helpful staff and the clean rooms in our reviews. Popular ...
8/10 Very Good! (1,002 reviews)
Good value
"I will stay here again. Good value. One of the biggest rooms I have ever stayed in."

Reviewed on Jul 21, 2025

Sugar Loaf Lodge
See all 595 properties in Summerland Key
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.
Old Florida Style, wrap around porch, boat basin for dockage, open water

Old Florida Style, wrap around porch, boat basin for dockage, open water

Little Torch Key
Stay at this vacation home in Summerland Key. Enjoy a garden, laundry facilities, and cable/satellite TV service. Popular attractions Big Pine Key Flea Market ...
9.6/10 Exceptional! (76 reviews)
Cool dock
"The secluded dock is a nice feature. The driveway is tricky to exit."

Reviewed on Jun 20, 2025

Old Florida Style, wrap around porch, boat basin for dockage, open water
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!

Cudjoe Key
Stay at this vacation home in Summerland Key. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Florida Keys Beaches and Venture ...
10/10 Exceptional! (3 reviews)
"The place was just as pictured, very comfortable and private. Very clean and spacious. The only issue we had was trying to get the back door to lock."

Reviewed on Apr 29, 2025

JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Waterfront Home

Waterfront Home

Cudjoe Key
Stay at this cottage in Summerland Key. Enjoy laundry facilities, tennis courts, and a pool table. Popular attractions Florida Keys Beaches and Venture Key are ...
8.6/10 Excellent! (165 reviews)
Cudjoe key
"The house was cozy and a great view of the canal. I like how they had a bathtub and shower with a sliding door and many cabinets and space for things."

Reviewed on Jun 22, 2025

Waterfront Home
See all properties in Summerland Key
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.

Popular places to visit

Upper Sugarloaf Sound

Upper Sugarloaf Sound

Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.

Upper Sugarloaf Sound

Sugarloaf Beach

Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?

Sugarloaf Beach

Upper Sugarloaf Key

4/5(21 reviews)

Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.

Upper Sugarloaf Key

Crab Key

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

Crab Key

Squirrel Key

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

Squirrel Key

Pye Key

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

Pye Key

Things to do

A fun-filled adventure for the whole family

Guided Clear Kayak Eco-Tour Near Key West

￥11,581
per adult
Guided Clear Kayak Eco-Tour Near Key West
Marathon Backcountry Permit

Marathon Backcountry Fishing Charter

￥97,776
per traveler
Marathon Backcountry Fishing Charter
12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

￥4,022
per adult
78% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

￥4,022
per adult
Full Day Trip in Key West from Miami
Key West Day Trip & Glass Bottom-Boat Tour from Miami

Key West Day Trip & Glass Bottom-Boat Tour from Miami

￥18,910
per traveler
Key West Day Trip & Glass Bottom-Boat Tour from Miami
Key West Parasailing Downtown

Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides

￥8,795
per traveler
90% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
See all activities in Summerland Key

Cities near Summerland Key

South Beach featuring tropical scenes, general coastal views and a beach

Key West

Big Pine Key featuring a river or creek, a bay or harbor and general coastal views

Big Pine Key