Summerland Key Holidays
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Our guide on where to stay in Summerland Key
Find the best Summerland Key areas and neighborhoods for the activities you enjoy most. Learn more about 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.
Summerland Key Holiday
Our pick of the best Summerland Key Hotel Deals
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
7.6/10 Good! (1,002 reviews)
Clean, very hospitable, will return.
Reviewed on 27 Feb 2026
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is NZ$576 per night from 29 Mar to 30 Mar
NZ$576
29 Mar - 30 Mar
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
Clean, quiet. Waterfront. Minimal “breakfast”. Plenty parking. Pricey. Standard room very small but functional. Showing some wear but freshly painted, well landscaped. Free bikes.
Reviewed on 28 Feb 2026
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (495 reviews)
The property is immaculate. The room is more like an apartment and it feels brand new. So spacious and just perfect for a family. The staff could not have been nicer!
Reviewed on 28 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.
What to do in Summerland Key
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
NZ$46
per adult
92% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
NZ$97
per adult
88% of travellers recommend
Explore a world of travel with Expedia
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- Hotels near Boca Chica Nude Beach
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- Hotels near Key West Visitors Center
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- Summerland Key Hotels
- Smathers Beach
- Southernmost Point
- Fort East Martello Museum and Gallery
- Key West Cemetery
- Clarence S. Higgs Memorial Beach Park
- Mel Fisher Maritime Museum
- Boca Chica Nude Beach
- Big Pine Key Holidays
- Coco Plum Beach
- Mallory Square
- Pigeon Key
- Fort Zachary Taylor Historic State Park
- Key West Holidays
- Key West Butterfly and Nature Conservatory
- Florida Keys Beaches
- Duval Street
- Crane Point Museum and Nature Center
- South Beach
- Visit Big Torch Key
- Visit Port Pine Heights
- Visit Eden Pines
- Visit Lower Florida Keys
- Visit Big Pine Key
- Visit Sugarloaf Shores
- Visit Cudjoe Key
- Visit Melody Key
- Visit Ramrod Key
- Orlando Rental Cars in Bahia Honda Key
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- Discount Car Rentals Rental Cars in Lower Keys
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
