Summerland Key

Travel Guide

Summerland Key
Summerland Key
Summerland Key
Summerland Key
Summerland Key

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
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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 CA $148 per night from Sep 8 to Sep 9
CA $148
CA $212 total
Sep 8 - Sep 9
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)
"Great place all around, will be going back in the future!"

Reviewed on Aug. 16, 2025

Parmer's Resort
Sugar Loaf Lodge

Sugar Loaf Lodge

2.5 out of 5
17001 Overseas Hwy, Summerland Key, FL
The price is CA $137 per night from Aug 24 to Aug 25
CA $137
CA $154 total
Aug 24 - Aug 25
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! (998 reviews)
"Great sleep"

Reviewed on Aug. 20, 2025

Sugar Loaf Lodge
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! (427 reviews)
"Staff was very nice and friendly. The resort itself if clean and spacious. There’s a lot of good spots to eat at within a 15 minute drive. The beach was nice and clean"

Reviewed on Aug. 14, 2025

Get rates
Sugarloaf Key Hotel at KOA Resort
See all 608 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! (77 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
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key
Stay at this cottage in Summerland Key. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are ...
9/10 Wonderful! (85 reviews)
Lovely Keys Getaway
"The cottage was perfect for me and my 3 kids. We loved the location being less than a 30min drive from both Key West and Marathon, and within 20min of several beaches. The kids took a dip in the private pool in the back everyday. Check-in process was seamless, and the rooms were perfectly climate ..."

Reviewed on Jul. 9, 2025

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key
Stay at this cottage in Summerland Key. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Florida Keys Beaches and Venture ...
8.8/10 Excellent! (86 reviews)
Cuejoe key waterfront home
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."

Reviewed on Jun. 2, 2025

Canal front, dockage, 2 bedroom, 2 bath
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

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

12 hours Day at Key West With Boat Tour and Snorkeling

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

CA $38
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

CA $38
per adult
Full Day Trip in Key West from Miami
Key West & Parasailing Adventure from Miami

Key West & Parasailing Adventure from Miami

CA $171
per traveller
78% of travellers recommend
Key West & Parasailing Adventure from Miami
Passengers enjoying the shade on the Conch Tour Train in Key West

Key West Conch Tour Train

CA $62
per adult
88% of travellers recommend
Key West Conch Tour Train
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $77
per adult
86% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Day Trip & Snorkeling from Miami

Key West Day Trip & Snorkeling from Miami

CA $164
per traveller
72% of travellers recommend
Key West Day Trip & Snorkeling from Miami
See all activities in Summerland Key