Summerland Key Travel Guide
Tourist 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 Newfound Harbor Keys and Cook Island.
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! (1,002 reviews)
Staff was friendly. Room was clean. Furniture a little worn but bed comfortable and clean linens
Reviewed on 8 Jan 2026
Parmer's Resort
565 Barry Avenue Summerland Key FL
The price is AU$434 per night from 19 Jan to 20 Jan
AU$434
19 Jan - 20 Jan
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! (1,002 reviews)
Excellent
Reviewed on 5 Jan 2026
Sugar Loaf Lodge
17001 Overseas Hwy Summerland Key FL
The price is AU$335 per night from 19 Jan to 20 Jan
AU$335
19 Jan - 20 Jan
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! (999 reviews)
Great staff and great location!
Reviewed on 7 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.
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 ...
8.4/10 Very Good! (155 reviews)
This was exactly as advertised Small with everything you would need Not a luxurious 5 Star hotel but wasn’t advertised as one Cudjo key is perfect Several good restaurant (check out Morning Joint for breakfast) Will definitely come back
Reviewed on 26 Dec 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
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 ...
8/10 Very Good! (50 reviews)
A/C cold. Room clean. Good service. Priced right. Super cute property on the water. Just what I was looking for.
Reviewed on 14 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.
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.
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.
Activities
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
AU$86
per adult
88% of travellers recommend
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
AU$179
per adult
98% of travellers recommend
2-Hour Sunset Sailing With Wine In Stock Island
AU$187
per adult
Full-Day Trip to Key West from Miami
AU$112
per traveller
80% of travellers recommend
All-Inclusive Key West Beach Pass with Parasailing, Kayaks, Paddleboards
AU$164
per adult
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- Flights to Bahia Honda Key
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- Visit Eden Pines
- Visit Big Pine Key
- Visit Coral Gables
- Cow Key Holidays
- Visit Cow Key
- Visit Cutler Bay
- Visit Dredgers Key
- Visit Duck Key
- Visit Florida City
- Visit Key Biscayne
- Visit Key Colony Beach
- Visit Key Largo
- Visit Key West
- Visit Lignumvitae Key Botanical State Park
- Visit Long Key
- Visit Marco Island
- Visit Coconut Grove
- Visit Downtown Miami
- Visit Little Havana
- Visit Olympia Heights
- Visit Palmetto Bay
- Visit South Miami
- Visit Miami Springs
- Visit Miami
- Visit Sapphire Lakes
- Visit Ochopee
- Visit Ramrod Key
- Robbie's
- Sands Holidays
- Seven Mile Bridge
- Visit Stock Island
- Visit Ten Thousand Islands
