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 Upper Sugarloaf 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 Newfound Harbor Keys.
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and daily housekeeping. Our guests praise the bar and the helpful staff in their reviews. ...
7.4/10 Good! (1,006 reviews)
Very helpful staff
Reviewed on 3 Feb 2026
Parmer's Resort
565 Barry Avenue Summerland Key FL
The price is €310 per night from 8 Feb to 9 Feb
€310
8 Feb - 9 Feb
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 ...
8.8/10 Excellent! (1,003 reviews)
The rooms were very clean! Views were beautiful. Pool was heated the cool days we were there. The breakfast was good and fresh. Loved the afternoon tea, hot chocolate, and coffee selections. Staff were very welcoming!
Reviewed on 4 Feb 2026
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. ...
9.6/10 Exceptional! (480 reviews)
What a pleasant surprise. Over a holiday weekend, our other booking had overbooked us. We scrambled, and found this suite. It’s really, an apartment.. Oh my gosh, we were so happy. It was much better than the original lodging. There were two adults, two 21 year old sons. There was plenty of room ...
Reviewed on 3 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.
Private Secluded Ocean View & Pool Near Key West
Summerland Key FL
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, private pools and a fitness centre. Our guests praise the helpful staff in their reviews. Popular ...
8.2/10 Very Good! (99 reviews)
A wonderful time was had by all. Host was very responsive and we had no issues. Beautiful home and views!
Reviewed on 18 Nov 2025
Oceanfront home-shared swimming pool, dockage-just 20 miles from Key West
Cudjoe Key FL
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, laundry facilities and balconies. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
8.6/10 Excellent! (90 reviews)
It was good for what we wanted. The price point was really good. As others have stated, it is in need of some updates. The host was very communicative and very nice! We definitely enjoyed our stay and would consider staying there again.
Reviewed on 11 Aug 2025
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy laundry facilities, patios and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper Sugarloaf ...
8.2/10 Very Good! (56 reviews)
It was like staying at my Grandmom's house--it was clean but bathroom and kitchen cabinet needed some attention. Still, we were very happy with bungalow 12 and would stay there again.We only stayed overnight but the little pool, beach and fire pit would be quite enjoyable had we stayed longer. Great ...
Reviewed on 22 Jan 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 Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
Upper Sugarloaf Key
Commune with nature and explore the great outdoors at Upper Sugarloaf 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.
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.
Things to do
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
€43
per adult
88% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
€23
per adult
92% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
€33
per adult
88% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
€58
per adult
74% of travellers recommend
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