Two blue boats docked at a pier with a lighthouse in the background.
Photo by Brian V. Rowe
Open Photo by Brian V. Rowe

Sumter County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Sumter County Vacation

Book a vacation package to Sumter County and make travel planning a cinch. With all the details arranged before you leave, you can focus on enjoying every moment in this exciting destination. Get your trip to Sumter County off to a flying start by heading to its most famous cities. Wildwood is one you shouldn't miss. Start packing your suitcase, because your Sumter County vacation is just a few clicks away with Expedia.

Top destinations in Sumter County

The Latest Sumter County Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 7 - Jan 12

    Westgate Town Center Resort + Flight

    Kissimmee
    5 nights
    4.0 star property
    8.4/10 - Very good (2,068 reviews)
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • 1 stop
    CA $1,073
    CA $597
    per traveller
    found 1 day ago
    Westgate Town Center Resort
  • Jan 24 - Jan 28

    Westgate Cocoa Beach Resort + Flight

    Cocoa Beach
    4 nights
    4.0 star property
    8.6/10 - Excellent (577 reviews)
    "Great place!"
    Reviewed November 2, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    CA $1,703
    CA $966
    per traveller
    found 0 hours ago
    Westgate Cocoa Beach Resort
  • Dec 18 - Dec 23

    Margaritaville Cottages Orlando by Vstays with H2O Waterpark + Flight

    Kissimmee
    5 nights
    4.0 star property
    9.2/10 - Wonderful (1,000 reviews)
    Roundtrip • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • Nonstop MCO - YHM • Nonstop
    CA $2,449
    CA $1,400
    per traveller
    found 1 day ago
    Margaritaville Cottages Orlando by Vstays with H2O Waterpark
  • Dec 18 - Dec 23

    Evermore Orlando Resort + Flight

    Orlando
    5 nights
    4.0 star property
    9.6/10 - Exceptional (859 reviews)
    Roundtrip • Hamilton (YHM) - Orlando (MCO)
    YHM - MCO • Nonstop MCO - YHM • Nonstop
    Save 100% on your flight
    CA $3,927
    CA $2,371
    per traveller
    found 1 day ago
    Evermore Orlando Resort
  • Jan 19 - Jan 25

    Oceanique Resort + Flight

    Indian Harbour Beach
    6 nights
    3.5 star property
    9.2/10 - Wonderful (466 reviews)
    "Beautiful view of the ocean, small resort style , quiet and peaceful. Large shopping center is a 10 minute speed walk."
    Reviewed November 6, 2026
    Roundtrip • Toronto (YYZ) - Orlando (MCO)
    YYZ - MCO • Nonstop MCO - YYZ • Nonstop
    CA $2,140
    CA $1,320
    per traveller
    found 1 day ago
    Oceanique Resort

Discover the most popular places to visit in Sumter County

What to do in Sumter County

Sumter County Hotel Deals

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.

Frequently Asked Questions

How much does a Sumter County vacation package cost?

We make it easy to explore the world, with Sumter County packages starting from just CA $597. You'll have the flexibility to bundle your preferred airlines, hotels and car rental. For the ultimate escape, why not add a couple of experiences and tours to your itinerary?

How do I get a cheap travel package to Sumter County?

Secure flights that fit your busy schedule, add a hotel room to your booking and see how much you save with a Sumter County vacation package. It's as simple as that! From flights and hotels to rental cars and tours, Expedia makes traveling on a budget easy. And with over 550 partner airlines and 1,000,000 hotels all over the world to select from, you'll never be short of choice.

What are the top hotels in Sumter County?

For hotels in The Villages with friendly service and cozy beds, you can't beat Hilton Daytona Beach Oceanfront Resort and Daytona Grande Oceanfront Resort. If you're visiting Wildwood as well, you can look forward to a great night's sleep at Margaritaville Jacksonville Beach or The Island Resort at Fort Walton Beach.

How far in advance should I book my Sumter County vacation?

Reserving your flight early with Expedia means one less thing to have to worry about. Most air carriers display prices up to 12 months prior to take off. Generally, this is the cheapest time to book. If circumstances have left you booking late, incredible deals to Sumter County occasionally appear a few weeks before departure.

What does an Expedia Sumter County travel package include?

It's up to you! You can choose from a variety of Sumter County packages, such as a flight, rental car and hotel. You can also book a hotel and a flight, or a flight and a rental car. Once you've made your booking, you can add on the fun stuff like tours and activities. Whatever your Sumter County vacation looks like, you'll save!

What should I know before booking a Sumter County travel package?

You'll enjoy excellent savings when you combine your hotels, flights and rental cars into a travel package. Not just that, booking everything in one spot will make your trip planning easier. So why waste your time or money? Whether you're organizing a ritzy romantic getaway or a low-cost family road trip, browse our vacation packages today.

Can I choose my airline with a Sumter County Expedia vacation package?

Yes — and it's easy too. Expedia has access to more than 550 partner airlines around the world. Our vacation packages give you the flexibility to take your pick of available flight, hotel or activity options that fit your needs.

If I'm not able to travel, can I cancel my Sumter County vacation package?

You sure can, and we'll help you every step of the way. You may be able to change or cancel your Sumter County vacation package for free if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company if your booking is older than that. If your travel plans unexpectedly change, take a look at our Customer Service Portal for more information.

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