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 Upper Sugarloaf Sound and Florida Keys Beaches.
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 Crab Key.
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! (1,001 reviews)
Staff very polite and accommodating.
Reviewed on 21 Dec 2025
Parmer's Resort
565 Barry Avenue Summerland Key FL
The price is €211 per night from 13 Jan to 14 Jan
€211
13 Jan - 14 Jan 2026
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)
Room was clean and comfortable.
Reviewed on 10 Dec 2025
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is €190 per night from 4 Jan to 5 Jan
€190
4 Jan - 5 Jan 2026
includes taxes & fees
Stay at this hotel in Summerland Key. Enjoy free Wi-Fi, free parking and a marina. Our guests praise the helpful staff and the clean rooms in their reviews. ...
8/10 Very Good! (1,002 reviews)
Yes, the room were fairly clean, bathrooms are kind of old and a bit rusty, but the rooms are nice spacious , great view, nice balcony, the reception people did not seem to know a lot about the surroundings or be willing to share info, only had one map of key west, they could be a bit more 'tourist ...
Reviewed on 20 Dec 2025
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, Dockage, Swimming Pool (shared), just 20 miles from Key West
Cudjoe Key FL
Stay at this cottage in Summerland Key. Enjoy a garden, laundry facilities and cable/satellite TV service. Popular attractions Florida Keys Beaches and Upper ...
8.6/10 Excellent! (73 reviews)
It was a nice location. 30” from Key West.
Reviewed on 21 Nov 2025
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Cudjoe Key FL
Stay at this holiday home in Summerland Key. Enjoy free Wi-Fi, laundry facilities and concierge services. Popular attractions Florida Keys Beaches and Venture ...
9.6/10 Exceptional! (40 reviews)
Great place!
Reviewed on 29 Nov 2025
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! (98 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
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
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
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.
Crab Key
Commune with nature and explore the great outdoors at Crab Key during your travels in Summerland Key.
Squirrel Key
Commune with nature and explore the great outdoors at Squirrel 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
86% 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 Sunset Cruise & Glass Bottom Eco Tour
€55
per adult
74% of travellers recommend
Key West Haunted Tour : Ghosts & Gravestones
€34
per adult
88% of travellers recommend
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