
Summerland Key Vacations from ¥95,330
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.

The Penguin Hotel
South Beach
Price was ¥127,526, price is now ¥95,330 per person
¥95,330
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Miami (MIA)
8.2/10 Very Good! (1,440 reviews)
It was across the beach and near Starbucks and other places that we want to visit like Versace mansion. Everyone were friendly especially Carmen at the front desk. Carmen was helpful
Reviewed on Oct 9, 2025

President Hotel
South Beach
Price was ¥136,800, price is now ¥99,614 per person
¥99,614
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Miami (MIA)
8.4/10 Very Good! (1,825 reviews)
Me gustó bastante la habitación con balcón, cómoda, amplia y con un baño grande...
Reviewed on Oct 9, 2025

Bentley Hotel South Beach
South Beach
Price was ¥178,896, price is now ¥133,439 per person
¥133,439
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Memphis (MEM) to Miami (MIA)
9.2/10 Wonderful! (334 reviews)
Location is amazing, room confort and facilities really good. Staff very friendly and helpfull. I had an amazing experience.
Reviewed on Oct 9, 2025

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 Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Upper Sugarloaf Key are some notable places to visit nearby.
Find the Best Summerland Key Vacation Packages
Summerland Key Hotel Deals

Parmer's Resort
565 Barry Avenue, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is ¥16,193 per night from Oct 13 to Oct 14
¥16,193
¥23,150 total
Oct 13 - Oct 14
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"Clean room , many options for guests to do around property. Close to key west and marathon"
Reviewed on Sep 10, 2025

Sugar Loaf Lodge
17001 Overseas Hwy, Summerland Key, FL
Fully refundableReserve now, pay when you stay
The price is ¥17,992 per night from Oct 13 to Oct 14
¥17,992
¥20,242 total
Oct 13 - Oct 14
includes taxes & fees
8/10 Very Good! (998 reviews)
"This was an excellent value for the price - the room was spacious and clean, the property was quiet. There was a beautiful view with a balcony. I could not have been happier with my experience!"
Reviewed on Oct 6, 2025

Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939, Summerland Key, FL
9.6/10 Exceptional! (439 reviews)
"It was great!"
Reviewed on Oct 7, 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.
What to do in Summerland Key

Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
¥11,711
per traveler
92% of travellers recommend

Key West Sunset Cruise & Glass Bottom Eco Tour
¥9,422
per adult
74% of travellers recommend

Historic Key West Old Town Trolley Hop-On Hop-Off Tour
¥8,144
per adult
86% of travellers recommend
Other vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.