Sumter County Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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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
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 $1,198, price is now CA $614 per person
CA $614
per person
May 1 - May 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Orlando (MCO)
8/10 Very Good! (1,703 reviews)
Check in staff was great! She upgraded my room to a one bed room with full kitchen. I didn't give it 5 stars because too much resort fees.

Reviewed on Feb 20, 2026

Westgate Lakes Resort & Spa Universal Studios Area

Westgate Lakes Resort & Spa Universal Studios Area

4 out of 5
Price was CA $1,337, price is now CA $675 per person
CA $675
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.2/10 Very Good! (5,482 reviews)
Everyone and Everything ..5 Stares..

Reviewed on Feb 20, 2026

Westgate Town Center Resort

Westgate Town Center Resort

4 out of 5
Price was CA $1,293, price is now CA $656 per person
CA $656
per person
Mar 27 - Apr 1
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8/10 Very Good! (1,367 reviews)
Great stay fo family. Lots of things to do.

Reviewed on Feb 20, 2026

Westgate Towers Resort

Westgate Towers Resort

3.5 out of 5
Price was CA $1,340, price is now CA $700 per person
CA $700
per person
Mar 27 - Apr 1
found 11 hours ago
Roundtrip flight included
Hamilton (YHM) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Such a beautiful property! Clean rooms, friendly and helpful staff. Relaxing stay, well most certainly return.

Reviewed on Feb 19, 2026

Residence Inn by Marriott Daytona Beach Oceanfront

Residence Inn by Marriott Daytona Beach Oceanfront

3 out of 5
Price was CA $3,309, price is now CA $1,771 per person
CA $1,771
per person
May 15 - May 22
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Staff very friendly. Spacious room. Great view. Our room was not cleaned everday, don't know if they were too busy. We did get service when we asked.

Reviewed on Dec 29, 2025

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Sumter County Hotel Deals

The Waterfront Inn

The Waterfront Inn

3 out of 5
1105 Lake Shore Drive The Villages FL
The price is CA $274 per night from Feb 23 to Feb 24
CA $274
CA $293 total
Feb 23 - Feb 24
includes taxes & fees
9.2/10 Wonderful! (1,335 reviews)
Clean and nice hotel! Housekeeping was performed flawlessly and daily . Definitely a great place to stay

Reviewed on Feb 19, 2026

The Waterfront Inn
Brownwood Hotel & Spa

Brownwood Hotel & Spa

3 out of 5
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
9.8/10 Exceptional! (1,118 reviews)
Room was spotless. Staff was very friendly and helpful. Pool was warm and inviting. Such a nice place to spend some time.

Reviewed on Feb 20, 2026

Get rates
Brownwood Hotel & Spa
Holiday Inn Express & Suites Wildwood The Villages by IHG

Holiday Inn Express & Suites Wildwood The Villages by IHG

3.5 out of 5
928 East State Road 44 Wildwood FL
Fully refundableReserve now, pay when you stay
The price is CA $126 per night from Mar 22 to Mar 23
CA $126
CA $134 total
Mar 22 - Mar 23
includes taxes & fees
9.4/10 Exceptional! (1,010 reviews)
ROOM VERY CLEAN GREAT BREAKFAST EXCELLENT STAFF

Reviewed on Feb 20, 2026

Holiday Inn Express & Suites Wildwood The Villages by IHG
See all 1,445 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 $614. 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.