Sumter County Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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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

A lighthouse silhouetted against a sunset over a body of water.
FlightsFlightsHotelsHotels

The Villages

The Villages
A river surrounded by dense forest with clear water and exposed tree roots.
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Wildwood

Wildwood

Top Sumter County Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $1,397, price is now CA $818 per person
CA $818
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (80 reviews)
The room was a little noisy from the air conditioner and outside noise. The shower was way to high.

Reviewed on Jun 19, 2026

Westgate Palace Hotel / Universal / I-Drive

Westgate Palace Hotel / Universal / I-Drive

4 out of 5
International Drive District
Price was CA $2,095, price is now CA $988 per person
CA $988
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9/10 Wonderful! (1,275 reviews)
Family oriented

Reviewed on Jul 10, 2026

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

Margaritaville Cottages Orlando by Vstays with H2O Waterpark

4 out of 5
Price was CA $3,607, price is now CA $2,128 per person
CA $2,128
per person
Aug 16 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
9.2/10 Wonderful! (1,003 reviews)
The cottage was great, check-in was easy and efficient. Only concern was there were no replacements for garbage bags that were used, I guess that goes with the self-sufficiency in the cottages.

Reviewed on Jul 10, 2026

ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $2,193, price is now CA $1,300 per person
CA $1,300
per person
Sep 12 - Sep 19
found 23 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Tampa (TPA)
9.6/10 Exceptional! (1,206 reviews)
It was new and updated! I loved my stay there!

Reviewed on Jul 10, 2026

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

Ramada Plaza Resort & Suites by Wyndham Orlando Intl Drive

3 out of 5
International Drive District
Price was CA $1,531, price is now CA $916 per person
CA $916
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Orlando (MCO)
7.8/10 Good! (524 reviews)
👍

Reviewed on Jul 10, 2026

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 $143 per night from Jul 15 to Jul 16
CA $143
CA $153 total
Jul 15 - Jul 16
includes taxes & fees
9.2/10 Wonderful! (1,444 reviews)
"The pool area was great, location of property was convenient walking to local restaurants and shops"

Reviewed on Jul 9, 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
The price is CA $149 per night from Jul 21 to Jul 22
CA $149
CA $159 total
Jul 21 - Jul 22
includes taxes & fees
9.8/10 Exceptional! (1,275 reviews)
"Pleasantly surprised. I was not expecting this nice of a hotel for the dollar value. I got a suite and it was great. I will always stay in this hotel when in the area. Highly recommend."

Reviewed on Jul 11, 2026

Brownwood Hotel & Spa
Hotel Eastport

Hotel Eastport

2 out of 5
7065 Beebe Court Wildwood FL
Fully refundableReserve now, pay when you stay
The price is CA $157 per night from Jul 12 to Jul 13
CA $157
CA $168 total
Jul 12 - Jul 13
includes taxes & fees
9.6/10 Exceptional! (228 reviews)
"Nice"

Reviewed on Jul 10, 2026

Hotel Eastport
See all 1,433 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
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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 $818. 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.

Stay near popular Sumter County attractions

Brownwood Paddock Square

You can enjoy retail therapy at Brownwood Paddock Square during your visit to Wildwood. Discover the live music and shops in this family-friendly area.
See properties

What to do in Sumter County

Gypsy Gold Horse Farm Tour

Gypsy Gold Horse Farm Tour

CA $78
per adult
100% of travellers recommend
Gypsy Gold Horse Farm Tour
See all activities in Sumter County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.