Sumter County Vacations & Trips from $227
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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 Towers Resort
Price was $559, price is now $227 per person
$227
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,002 reviews)
Room was clean and staff was friendly, however, property is outdated. Needs renovation.
Reviewed on Feb 25, 2026
Extended Stay America Suites Orlando Conv Ctr Universal Blvd
International Drive District
Price was $1,567, price is now $367 per person
$367
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
6.4/10 (1,001 reviews)
Staff was very accomidating but the hotel room wasnt clean.
Reviewed on Feb 21, 2026
Westgate Palace Hotel / Universal / I-Drive
International Drive District
Price was $1,212, price is now $442 per person
$442
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.8/10 Excellent! (1,085 reviews)
Room was amazing. Fully fenced in 24/7 security team. Also very nice area check out slap noodles within walking distance for a great meal. Only downsides were shower heads were a little eh and hot tub wasn’t functioning correctly.
Reviewed on Feb 24, 2026
Westgate Vacation Villas Resort
Price was $574, price is now $232 per person
$232
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,703 reviews)
The room with clean and although we did not take advantage of all the amenities the option to have was perfect.
Reviewed on Feb 25, 2026
Westgate Town Center Resort
Price was $622, price is now $257 per person
$257
per person
May 7 - May 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8/10 Very Good! (1,367 reviews)
It was a fun resort for myself, wife, and 8 year old daughter. There was so much do to . We enjoyed the water park, minigolf, arcade, and the Mexican restaurant. Walmart was walking distance. Unfortunately the only downside was there aren’t really any restaurants within reasonable walking distance. Also it seems the pizza place for room service doesn’t exist anymore, even though it’s on their website.
Reviewed on Feb 26, 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
The Waterfront Inn
1105 Lake Shore Drive The Villages FL
$202 nightly
The price is $216 total per night from Mar 29 to Mar 30
$216 total
Mar 29 - Mar 30
Total with taxes and fees
9.2/10 Wonderful! (1,333 reviews)
Clean, great amenities and staff were all so nice
Reviewed on Feb 25, 2026
Brownwood Hotel & Spa
3003 Brownwood Blvd Wildwood FL
Fully refundableReserve now, pay when you stay
$197 nightly
The price is $211 total per night from Mar 1 to Mar 2
$211 total
Mar 1 - Mar 2
Total with taxes and fees
9.8/10 Exceptional! (1,108 reviews)
Staff was friendly, pleasant, and enjoyed visit
Reviewed on Feb 24, 2026
Holiday Inn Express & Suites Wildwood The Villages by IHG
928 East State Road 44 Wildwood FL
Fully refundableReserve now, pay when you stay
$104 nightly
The price is $111 total per night from Mar 15 to Mar 16
$111 total
Mar 15 - Mar 16
Total with taxes and fees
9.4/10 Exceptional! (1,017 reviews)
Clean comfortable room, staff was very pleasant!
Reviewed on Feb 25, 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.
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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.