Summerland Key
Travel Guide
Visit Summerland Key
Where to stay in Summerland Key
Cutthroat Harbor Estates
While there might not be top attractions in Cutthroat Harbor Estates, you can explore the larger area and discover places like Venture Out Keys and Venture Key.
Sugarloaf Shores
Though Sugarloaf Shores may not have many top sights, you can venture to the surrounding area to see attractions like Florida Keys Beaches and Sugarloaf Beach.
Cudjoe Gardens
While Cudjoe Gardens may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Upper Sugarloaf Key and Upper Sugarloaf Sound.
Breezeswept Beach Estates
While there might not be top attractions in Breezeswept Beach Estates, you can explore the larger area and discover places like Cook Island and Munson Island.
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and a private beach. Our guests praise the helpful staff and the clean rooms in their reviews. ...
9.8/10 Exceptional! (521 reviews)
Everything was wonderful - staff, location, property condition, room
Reviewed on 26 Mar 2026
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is €229 per night from 26 Apr to 27 Apr
€229
26 Apr - 27 Apr
includes taxes & fees
Stay at this beach motel in Summerland Key. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff in their ...
9/10 Wonderful! (1,000 reviews)
Within easy reach of Key West
Reviewed on 24 Mar 2026
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
The price is €206 per night from 9 Apr to 10 Apr
€206
9 Apr - 10 Apr
includes taxes & fees
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
7.6/10 Good! (1,000 reviews)
Tiki Bar had great tacos, but the services was a little slow.
Reviewed on 25 Mar 2026
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.
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are ...
8.6/10 Excellent! (166 reviews)
Yes you are on the ocean, yes there are docks, and yes you are centrally located for activities. Cottage was clean but very dated and not well kept. It is not private, we had people walking and driving in and around us throughout the day. We did bring a dog, which is why we liked the private description, ...
Reviewed on 18 Mar 2026
Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy laundry facilities, patios and an in-room coffee maker. Popular attractions Florida Keys Beaches and Venture Key ...
8.8/10 Excellent! (96 reviews)
The photo shot from above from the outside of the building is abit misleading. The lower building on the left is the apartment and the high building next to it is a large separate home, so you can’t actually see the bay unless you walk to the water edge for a slight bay view. The houses across the ...
Reviewed on 12 Mar 2026
Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy a garden, laundry facilities and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key are located ...
8.6/10 Excellent! (162 reviews)
Great house, so clean Nicole was so pleasant and responsive
Reviewed on 18 Feb 2026
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
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Upper Sugarloaf Key
Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.
Upper Sugarloaf Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
Crab Key
Commune with nature and explore the great outdoors at Crab Key during your travels in Summerland Key.
Venture Key
Commune with nature and explore the great outdoors at Venture Key during your travels in Summerland Key.
Pye Key
Commune with nature and explore the great outdoors at Pye Key during your travels in Summerland Key.
Things to do
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
€50
per adult
88% of travellers recommend
Key West Mangrove Kayak Eco Tour
€69
per adult
100% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
€24
per adult
90% of travellers recommend
Key West Dolphin & Snorkeling Tour - Small Group
€116
per adult
100% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
€34
per adult
88% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
€60
per adult
76% of travellers recommend
Explore a world of travel with Expedia
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