Osceola County Vacations & Trips from $530
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Your Osceola County Vacation
Head off on your next thrilling adventure with an Osceola County vacation package, and leave knowing the finer details are taken care of. And with the ability to tailor your escape, you know it'll be one to remember. Get your trip to Osceola County off to a great start by exploring its top cities. Saint Cloud is one you shouldn't miss. If you're ready to stop dreaming and start doing, Expedia will help turn your Osceola County vacation into a reality.
Top destinations in Osceola County
The Latest Osceola County Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Westgate Lakes Resort & Spa Universal Studios Area
$749
per person
Dec 26 - Jan 1
found 1 day ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.4/10 Very Good! (7,160 reviews)
Great stay from start to finish!
Everything we wanted & needed all in one property. We will be back!!
Reviewed on Oct 20, 2026
Westgate Towers Resort
$1,053
per person
Dec 23 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,004 reviews)
We stayed 2 nights and were disappointed. Our room wasn't cleaned on the second day. The blackout curtains failed to block out the bright exterior lights at night. The beds are advertised as Queen, but they are definitely Full-sized. On top of that, the bathroom and shower are tiny and uncomfortable anyone tall or larger will struggle to even get through the bathroom door or shower properly.
Reviewed on Oct 19, 2026
Find the Best Osceola County Vacation Packages
Osceola County Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Orlando Intl. Airport (MCO) |
Top Sights | Lake Tohopekaliga, Lakefront Park and Alligator Lake |
Osceola County Hotel Deals
Kompose Boutique Resort at Theme Parks
7491 W Irlo Bronson Memorial Hwy Kissimmee FL
Fully refundableReserve now, pay when you stay
$69 nightly
$78 total
Oct 28 - Oct 29
Total with taxes and fees
9.4/10 Exceptional! (6,142 reviews)
"The only complaint that I have is when we went to the restaurant by the pool, the tall white guy waiter was not prompt. He helped a lot of other people before us just had Bad server service."
Reviewed on Oct 19, 2026
Seasons Florida Resort
4736 W Irlo Bronson Hwy Memorial Kissimmee FL
Fully refundableReserve now, pay when you stay
$42 nightly
$47 total
Oct 21 - Oct 22
Total with taxes and fees
Margaritaville Resort Orlando with H2O Waterpark
8000 Fins Up Circle Kissimmee FL
Fully refundableReserve now, pay when you stay
$184 nightly
$209 total
Nov 3 - Nov 4
Total with taxes and fees
8.8/10 Excellent! (3,791 reviews)
"Really nice place, I will be back, that's for sure!!"
Reviewed on Oct 19, 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 Osceola County attractions
ESPN Wide World of Sports Complex
8.6/10 (1,630 reviews)
Catch an event at ESPN Wide World of Sports Complex, and enjoy other activities in Lake Buena Vista such as golfing. Experience the entertainment choices and acclaimed theater scene in this family-friendly area.
Old Town
8.6/10 (14,011 reviews)
Enjoy the excitement at Old Town and see why people love this theme park in Kissimmee. Check out the shops and top-notch restaurants in this family-friendly area.
Photo by Visit Orlando
Mystic Dunes Golf Club
7.8/10 (4,134 reviews)
Tee off at one of Orlando’s premier golf clubs and enjoy the championship course, the excellent facilities and the laid-back Florida vibe.
Kissimmee Lakefront Park
8.4/10 (2,921 reviews)
Kissimmee Lakefront Park is just one of the places to see in Kissimmee, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or experience the entertainment choices in this family-friendly area.
Medieval Times
8.0/10 (3,178 reviews)
You can get tickets for a performance at Medieval Times on your trip to Kissimmee. Make time for the shops and golf courses in this family-friendly area.
Photo by Emily Slade
Boggy Creek Airboat Rides
7.8/10 (463 reviews)
Take the family on an outing to Boggy Creek Airboat Rides during your trip to Kissimmee. Stroll along the lakeside or attend a sporting event in the area.
Reunion Resort Golf Course
7.6/10 (3,040 reviews)
Enjoy a round of golf in Kissimmee at Reunion Resort Golf Course. Amble around this family-friendly area's lakeside, or seek out the local tours.
ChampionsGate Golf Club
8.0/10 (1,507 reviews)
Enjoy a round of golf in Four Corners at ChampionsGate Golf Club. Discover the top-notch restaurants and entertainment choices in this family-friendly area.
What to do in Osceola County
Icon Park: SEA LIFE Aquarium, Madame Tussauds or The Orlando Eye Options
$31
per adult
92% of travellers recommend
Universal Orlando Resort Express Passes
$128
per traveler
80% of travellers recommend
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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.
