Sumter County Vacations & Trips from $295
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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 destinations in Sumter County
The Villages
The Latest Sumter County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was $1,258, price is now $484 per person
$484
per person
Sep 23 - Sep 30
found 10 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9/10 Wonderful! (1,275 reviews)
Clean room and supportive staff
Reviewed on Jul 13, 2026
Westgate Towers Resort
Price was $721, price is now $309 per person
$309
per person
Sep 23 - Sep 30
found 21 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.6/10 Excellent! (1,003 reviews)
Amenity restaurants were offsite across the street in a gated Villa community. Very inconvenient
Reviewed on Jul 12, 2026
Margaritaville Cottages Orlando by Vstays with H2O Waterpark
Price was $2,865, price is now $1,458 per person
$1,458
per person
Aug 22 - Sep 1
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
9.2/10 Wonderful! (1,003 reviews)
Room was very dirty sheets not cleaned. Staff said sorry nothing they can do they don’t have any extras. We have pictures and phone call recording with front desk. Very poor experience and really deserve are money back tj be honest. Hot tub didn’t work so kids and us couldn’t use that either. House didn’t have a of any thing. No extra blankets towels trash bags anything.
Reviewed on Jul 13, 2026
CW Hotel
Save 100% on your flight
Price was $1,718, price is now $913 per person
$913
per person
Sep 12 - Sep 18
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Tampa (TPA)
No reviews
We had such a great stay at the CW Resort in Clearwater! The pool area was beautiful and relaxing, the views were amazing, and the entire property was very clean and well maintained. It was the perfect place to unwind and enjoy a Florida getaway. We would definitely stay here again!
Reviewed on Jul 8, 2026
Find the Best Sumter County Vacation Packages
Sumter County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Orlando Intl. Airport (MCO) |
Top Sights | Dade Battlefield State Park, Lake Deaton and The Florida International Teaching Zoo |
Sumter County Hotel Deals
Brownwood Hotel & Spa
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $112 total per night from Jul 27 to Jul 28
$112 total
Jul 27 - Jul 28
Total with taxes and fees
9.8/10 Exceptional! (1,281 reviews)
"This hotel was perfect for our stay with our dog. Everyone was so nice and helpful."
Reviewed on Jul 13, 2026
The Waterfront Inn
1105 Lake Shore Drive The Villages FL
$99 nightly
The price is $106 total per night from Jul 29 to Jul 30
$106 total
Jul 29 - Jul 30
Total with taxes and fees
9.2/10 Wonderful! (1,449 reviews)
"This is a wonderful place to stay. Close to everything to do. Staff super friendly & helpful. Pool beautiful with great scenery. We will be staying here everytime we visit."
Reviewed on Jul 12, 2026
Hotel Eastport
7065 Beebe Court Wildwood FL
Fully refundableReserve now, pay when you stay
$111 nightly
The price is $119 total per night from Jul 14 to Jul 15
$119 total
Jul 14 - Jul 15
Total with taxes and fees
9.6/10 Exceptional! (232 reviews)
"New hotel. Excellent room and staff."
Reviewed on Jul 13, 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.
Stay near popular Sumter County attractions
What to do in Sumter County
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
