Sugarloaf Key Beach Vacations

Book a Beach Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 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

Find your perfect Sugarloaf Key beach vacation

How do I book the best Sugarloaf Key beach vacation packages?

Life’s a beach when you dive into our brilliant Sugarloaf Key beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Sugarloaf Key?

A rental steps from the shore creates an amazingly affordable Sugarloaf Key beach vacation. Seaside sojourns during low season start from . Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Sugarloaf Key?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Sugarloaf Key beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Sugarloaf Key vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Sugarloaf Key beach vacation deals?

Sort your search results by deals to delight in amazing Sugarloaf Key beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Sugarloaf Key beach trip with free cancellation and/or flexible dates?

Just like the Sugarloaf Key tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Sugarloaf Key beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Sugarloaf Key. (OK, maybe not that last part.)

Top Beach Sugarloaf Key Hotels

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

3 out of 5
251 Co Rd 939, Summerland Key, FL
  • 10 min drive from Florida Keys Beaches
Stroll along the shore in Summerland Key, as you'll be within walking distance of a private beach when booking a getaway at this hotel. Amenities at Sugarloaf ...
9.6/10 Exceptional! (439 reviews)

Travelers like: on the beach, outdoor pool

Travelers say...
"It was great!"

Reviewed on Oct 7, 2025

Sugarloaf Key Hotel at KOA Resort
Sublimely private luxury home with enveloping oceanfront views near Key West

Sublimely private luxury home with enveloping oceanfront views near Key West

Near Key West
  • 9 min drive from Florida Keys Beaches
At this vacation home, get ready to stroll along the shore in Summerland Key, as you'll be within walking distance of the beach. A hot tub and a sauna are just ...
9.2/10 Wonderful! (21 reviews)

Travelers like: on the beach, private pool

Top Notch Experience
"There are no words to describe how wonderful this property is! From the very beginning to the sad ending (because we had to leave), it was a fantastic location, and the house had everything we needed. We stayed in and cooked almost every night and the amenities never disappointed! The view cannot ..."

Reviewed on May 7, 2025

Sublimely private luxury home with enveloping oceanfront views near Key West
Florida Keys Beach Getaway

Florida Keys Beach Getaway

Upper Sugarloaf Key
  • 3 min walk from Florida Keys Beaches
You will love your stay at this vacation home and stroll along the shoreline in Summerland Key, as you'll be close to Sugarloaf Beach.
9.6/10 Exceptional! (27 reviews)
Relaxing Visit to Key West
"This was a wonderful setting for us. We had dinners and a couple of outings in Key West, but then had a great time just sitting and walking on a quiet beach the rest of the time and enjoying life at our own pace.Cadmier was very helpful before our trip and Tom was a great source of info once we arrived. ..."

Reviewed on May 18, 2025

Florida Keys Beach Getaway
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.

More 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.