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 Key and Venture Out Keys.
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 Newfound Harbor Keys.
Parmer's Resort
565 Barry Avenue Summerland Key FL
The price is AU$485 per night from 31 Mar to 1 Apr
AU$485
31 Mar - 1 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! (1,005 reviews)
Nice clean room with kitchenette. Staff friendly, courteous, and helpful. Good amenities, pool, kayaks- no extra charge, beach, fresh bake cookies and lemonade in the afternoon. Good restaurant just down the street. Discount offered at restaurant for staying at the motel.
Reviewed on 1 Mar 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. ...
9.8/10 Exceptional! (497 reviews)
Room was spacious with a great view ! Pet friendly! I couldn’t ask for a better stay honestly.
Reviewed on 2 Mar 2026
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. ...
7.6/10 Good! (1,002 reviews)
Clean, very hospitable, will return.
Reviewed on 27 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.
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! (161 reviews)
The host (Susan) is awesome. When ever I messaged her she would respond quickly. Never had any issues and this was our 3rd year vacationing at these cottages. We’ll definitely be back.
Reviewed on 15 Feb 2026
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key FL
Stay at this holiday home in Summerland Key. Enjoy a garden, laundry facilities and patios. Popular attractions Florida Keys Beaches and Upper Sugarloaf Key ...
9/10 Wonderful! (160 reviews)
We had an incredible stay! The space was clean, stylish, and perfectly located. It made our Keywest trip even more special. Would 100% book again!
Reviewed on 16 Feb 2026
Private Oceanfront Cottage with dockage, pool 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! (165 reviews)
Did not use tge pool, it looked nice. The place is a little worn and dated. It was clean, everything worked as it should. Tough thing to find in the keys, it was very private. 4 places spred out over a long property. I could only see 2 houses, about the same when you went on the dock. Dock was nice, ...
Reviewed on 30 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
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.
Venture Key
Commune with nature and explore the great outdoors at Venture 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.
Activities
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
AU$86
per adult
88% of travellers recommend
Round-trip Transportation to Key West from Miami
AU$106
per adult
Key West Dolphin & Snorkeling Tour - Small Group
AU$191
per adult
Key West's Island Eco Tour: Sandbar Adventure with Kayaking Tour
AU$170
per adult
98% of travellers recommend
2-Hour Sunset Sailing With Wine In Stock Island
AU$177
per adult
Full-Day Trip to Key West from Miami
AU$106
per traveller
80% of travellers recommend
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- Flights to Bahia Honda Key
- Flights to Boca Chica Key
- Flights to Lower Florida Keys
- Flights to Rockland Key
- Flights from Key West Intl.
- Flights from Little Torch Key
- Flights from Charlotte to Sugarloaf Key
- Flights from Boca Chica Key
- Flights from Melody Key
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- Flights from New York (JFK) to Key West (EYW)
- Flights from Los Angeles (LAX) to Key West (EYW)
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- Flights from Sydney (SYD) to Key West (EYW)
- 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
