Sumter County Vacation Packages
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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
The Villages
Wildwood
Top Sumter County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Westgate Cocoa Beach Resort
CA $2,068
per person
Sep 18 - Sep 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Orlando (MCO)
8.6/10 Excellent! (556 reviews)
It is a time share property not a resort.
It has very little amenities and does not offer day to day room cleaning. We had to take our own trash out order fresh towels and go to store to buy shower items. None of this was listed in the details.
The place is old and tired, it needs a fresh coat of everything.
Kids are un supervised in the pool area and you cannot relax.
If you are hoping for a refreshing time this is not the place it’s very expensive and not worth the money. The beach walk is very hard to find. The map they offer does not depict the most accurate information.
There is no room service and the “restaurant” on property is very limited
Not worth the money at all
Reviewed on Jul 31, 2026
Sumter County Hotel Deals
Brownwood Hotel & Spa
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
CA $157
CA $168 total
Sep 1 - Sep 2
includes taxes & fees
The Waterfront Inn
1105 Lake Shore Drive The Villages FL
CA $151
CA $161 total
Aug 19 - Aug 20
includes taxes & fees
9.2/10 Wonderful! (1,474 reviews)
"Room was clean and bed was very comfortable. The downside was"
Reviewed on Aug 9, 2026
Hotel Eastport
7065 Beebe Court Wildwood FL
Fully refundableReserve now, pay when you stay
CA $161
CA $172 total
Aug 19 - Aug 20
includes taxes & fees
9.6/10 Exceptional! (254 reviews)
"Yamas restaurant was excellent and extremely friendly staff, hotel was so clean and staff were so polite an helpful. Would highly recommend and will definitely stay there again"
Reviewed on Aug 7, 2026
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 $576. 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.
The Villages Market Square
9.2/10 (669 reviews)
You can enjoy retail therapy at The Villages Market Square during your visit to The Villages. Wander the lakeside in this quaint area.
Webster Westside Flea Market
8.4/10 (40 reviews)
You can do some window-shopping at Webster Westside Flea Market during your trip to Webster. You can enjoy the coffeehouses while in the area.
Lake Okahumpka Park
8.6/10 (38 reviews)
Explore the great outdoors at Lake Okahumpka Park, a lovely green space in Wildwood. Discover the entertainment venues in this quaint area, or seek out its golf courses.
Glenview Champions Country Club
9.0/10 (43 reviews)
Enjoy a round of golf in The Villages at Glenview Champions Country Club. While in this family-friendly area, you can savor the top-notch restaurants.
Continental Country Club
8.0/10 (39 reviews)
Enjoy a round of golf in Wildwood at Continental Country Club. Discover the coffeehouses and entertainment venues in this quaint area.
Dade Battlefield State Park
6.8/10 (5 reviews)
You can take time to visit Dade Battlefield State Park during your travels to Bushnell. Take in the festivals while you're in the area.
Cane Garden Country Club
9.0/10 (55 reviews)
Enjoy a round of golf in The Villages at Cane Garden Country Club. Discover the coffeehouses and entertainment venues in this family-friendly area.
What to do in Sumter County
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
