Summerland Key Holidays
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to NZ$616 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 Out Keys and Venture Key.
Summerland Key Holiday
Our pick of the best Summerland Key Hotel Deals
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (551 reviews)
Enjoyed our time there
Reviewed on 13 Apr 2026
Parmer's Resort
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is NZ$394 per night from 27 Apr to 28 Apr
NZ$394
27 Apr - 28 Apr
includes taxes & fees
9/10 Wonderful! (1,016 reviews)
Excellent place for a family getaway.
Reviewed on 13 Apr 2026
Looe Key Reef Resort
27340 Overseas Highway Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is NZ$463 per night from 10 May to 11 May
NZ$463
10 May - 11 May
includes taxes & fees
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$47
per adult
88% of travellers recommend
Key West Mangrove Kayak Eco Tour
NZ$136
per adult
100% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
NZ$95
per adult
88% of travellers recommend
Explore a world of travel with Expedia
- Apartments in Sugarloaf Key
- Cottages in Cudjoe Key
- Resort in Little Torch Key
- Caravan Parks in Boca Chica Key
- Motels in Lower Keys
- Resort in Lower Keys
- Resort in Lower Florida Keys
- Caravan Parks in Lower Florida Keys
- Hostels in Lower Florida Keys
- Motels in Lower Florida Keys
- Villas in Bahia Honda Key
- Lodges in Bahia Honda Key
- Resort in Bahia Honda Key
- Hersha Hospitality Hotels in Lower Florida Keys
- Beach Hotels in Boca Chica Key
- Cheap Hotels in Boca Chica Key
- Beach Hotels in Big Pine Key
- Spa Hotels in Big Pine Key
- Cheap Hotels in Big Pine Key
- Golf Hotels in Little Torch Key
- Cheap Hotels in Lower Florida Keys
- Luxury Hotels in Lower Florida Keys
- Beach Hotels in Lower Florida Keys
- Hotels with Pool in Lower Florida Keys
- Cheap Hotels in Lower Sugarloaf Key
- Sugarloaf Shores Hotels
- Big Pine Key Hotels
- Hotels near Boca Chica Nude Beach
- Cow Key Hotels
- Hotels near Key West Visitors Center
- Hotels near Coupon Bight Aquatic Preserve
- 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
- Island Car Rentals Rental Cars in Bahia Honda Key
- Airport Van Rental Rental Cars in Bahia Honda Key
- Thrifty Car Rental Rental Cars in Lower Sugarloaf Key
- Avis Rental Cars in No Name Key
- Ace Rental Cars in No Name Key
- United Rental Cars in Sugarloaf Key
- Airport Van Rental Rental Cars in Sugarloaf Key
- Thrifty Car Rental Rental Cars in Melody Key
- Hertz Rental Cars in Lower Florida Keys
- Avis Rental Cars in Lower Florida Keys
- Budget Rental Cars in Lower Florida Keys
- Ace New Zealand Rental Cars in Lower Florida Keys
- Island Car Rentals Rental Cars in Lower Florida Keys
- Fox Rental Cars Rental Cars in Lower Florida Keys
- National Car Rental Rental Cars in Lower Florida Keys
- Global Rent a Car Rental Cars in Lower Florida Keys
- United Rental Cars in Lower Florida Keys
- Dollar Rent A Car Rental Cars in Lower Florida Keys
- 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.
