Summerland Key Vacations from ¥347,906

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥45,448 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Summerland Key Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Cavalier Hotel South Beach
Hotel Riu Plaza Miami Beach
The Penguin Hotel
President Hotel
Bentley Hotel South Beach

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

Find the Best Summerland Key Vacation Packages

Summerland Key Hotel Deals

Looe Key Reef Resort

Looe Key Reef Resort

2.5 out of 5
27340 Overseas Highway Summerland Key FL
7.6/10 Good! (1,000 reviews)
The room was clean the staff was amazing!! The Tiki Bar and food were great! The resort was perfect!

Reviewed on Feb 24, 2026

Looe Key Reef Resort
Parmer's Resort

Parmer's Resort

2.5 out of 5
565 Barry Avenue Summerland Key FL
Fully refundableReserve now, pay when you stay
The price is ¥43,358 per night from Mar 29 to Mar 30
¥43,358
¥53,865 total
Mar 29 - Mar 30
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
Room was outdated but clean and fresh and loved that it is near the boat dock around the corner- pool is super clean and warm- breakfast really good- Coffee not so good too strong!! Front desk staff very good got us things as we requested them clean towels and shower soap and toothbrushes- Grounds ...

Reviewed on Feb 26, 2026

Parmer's Resort
Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939 Summerland Key FL
9.8/10 Exceptional! (493 reviews)
Great rooms

Reviewed on Feb 26, 2026

Sugarloaf Key Hotel at KOA Resort
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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.