Sumter County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • 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 vacation destinations in Sumter County

FlightsFlightsHotelsHotels

The Villages

The Villages
Madison Blue Springs at Sunset, Madison Blue Springs State Park, Florida
FlightsFlightsHotelsHotels

Wildwood

Wildwood

Top Sumter County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Westgate Vacation Villas Resort

Westgate Vacation Villas Resort

4 out of 5
Price was CA $1,350, price is now CA $727 per person
CA $727
per person
Aug 7 - Aug 14
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
8.2/10 Very Good! (1,944 reviews)
i didn’t like it was faults advertising the water park in the facility was not included as it stated in the discrimination i payed over 200 a night and that was the only reason why i wanted to stay at this hotel and that was not included. i would not rent this plays out again for that price it’s way over priced

Reviewed on May 25, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $2,754, price is now CA $1,308 per person
CA $1,308
per person
Jul 1 - Jul 8
found 20 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Orlando (MCO)
8.8/10 Excellent! (1,253 reviews)
It was a very nice clean property just a bit smaller unit size than what we’re used to!

Reviewed on May 25, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,384, price is now CA $746 per person
CA $746
per person
Aug 7 - Aug 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
8.2/10 Very Good! (1,731 reviews)
The hotel stay was good

Reviewed on May 26, 2026

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was CA $1,344, price is now CA $727 per person
CA $727
per person
Aug 7 - Aug 14
found 21 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
8.6/10 Excellent! (1,001 reviews)
The room was clean staff was nice.i was good for the weekend stay really enjoyed it.

Reviewed on May 24, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $3,098, price is now CA $1,719 per person
CA $1,719
per person
Aug 17 - Aug 24
found 1 day ago
Roundtrip flight included
Halifax (YHZ) to Orlando (MCO)
9.2/10 Wonderful! (1,004 reviews)
Everything was excellent, except the pool definitely needed maintenance and cleaning.

Reviewed on May 26, 2026

Sumter County Hotel Deals

Brownwood Hotel & Spa

Brownwood Hotel & Spa

3 out of 5
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
The price is CA $167 per night from Jun 24 to Jun 25
CA $167
CA $179 total
Jun 24 - Jun 25
includes taxes & fees
9.8/10 Exceptional! (1,199 reviews)
"Great room, plush bedding, extremely clean. Room (and hotel) was beautifully decorated."

Reviewed on May 26, 2026

Brownwood Hotel & Spa
The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is CA $156 per night from May 31 to Jun 1
CA $156
CA $167 total
May 31 - Jun 1
includes taxes & fees
9.2/10 Wonderful! (1,405 reviews)
"Great place to stay and just a short bit from the town square. Happy hour at the restaurant and the pool are fun!"

Reviewed on May 27, 2026

The Waterfront Inn
Hampton Inn & Suites Lady Lake/The Villages

Hampton Inn & Suites Lady Lake/The Villages

3 out of 5
11727 Ne 63 Rd Dr Lady Lake FL
Fully refundableReserve now, pay when you stay
The price is CA $137 per night from Jun 10 to Jun 11
CA $137
CA $146 total
Jun 10 - Jun 11
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Really nice, clean place. I feel safe. Breakfast was delicious. I will go back to that place whenever necessary."

Reviewed on May 25, 2026

Hampton Inn & Suites Lady Lake/The Villages
See all 1,410 properties in Sumter County
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 $727. 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.