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 Vacation Villas Resort
Price was $751, price is now $295 per person
$295
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Orlando (MCO)
8.2/10 Very Good! (1,979 reviews)
Great property for families. The arcade is awesome, the waterpark gets well utilized and the property is exquisite as always with a Westgate Resort
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 1 day 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
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Save 100% on your flight
Price was $862, price is now $442 per person
$442
per person
Aug 22 - Aug 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
9/10 Wonderful! (1,275 reviews)
Clean room and supportive staff
Reviewed on Jul 13, 2026
CW Hotel
Save 100% on your flight
Price was $2,019, price is now $1,059 per person
$1,059
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) 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
ChartHouse Clearwater Beach Marina Hotel
Save 100% on your flight
Price was $1,308, price is now $695 per person
$695
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (1,206 reviews)
No problems! Clean room great location , staff was nice and and seamless stay.
Reviewed on Jul 13, 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
$104 nightly
The price is $112 total per night from Aug 11 to Aug 12
$112 total
Aug 11 - Aug 12
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
$96 nightly
The price is $103 total per night from Jul 29 to Jul 30
$103 total
Jul 29 - Jul 30
Total with taxes and fees
9.2/10 Wonderful! (1,450 reviews)
"THE STAFF WERE VERY FRIENDLY AND THE LOCATION IS GREAT!"
Reviewed on Jul 14, 2026
Hotel Eastport
7065 Beebe Court Wildwood FL
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $116 total per night from Jul 30 to Jul 31
$116 total
Jul 30 - Jul 31
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.
