Osceola County Vacations & Trips from $393
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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 Leisure Resort
International Drive District
$657
per person
Dec 5 - Dec 12
found 23 hours ago
Roundtrip flight included
Boston (BOS) to Orlando (MCO)
8.6/10 Excellent! (1,001 reviews)
This place was absolutely amazing! So much fun stuff to do with my kids, multiple pools and handicap accessible! Will definitely book again!
Reviewed on Oct 25, 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
$75 nightly
$85 total
Oct 28 - Oct 29
Total with taxes and fees
9.4/10 Exceptional! (6,221 reviews)
"Very clean, nice staff. Rob was very helpful"
Reviewed on Oct 26, 2026
Palazzo Lakeside Hotel
4944 W. Irlo Bronson Memorial Highway Kissimmee FL
$63 nightly
$71 total
Oct 27 - Oct 28
Total with taxes and fees
8.4/10 Very Good! (5,381 reviews)
"Great value. The hotel is perfect for doing theme parks."
Reviewed on Oct 26, 2026
Margaritaville Resort Orlando with H2O Waterpark
8000 Fins Up Circle Kissimmee FL
Fully refundableReserve now, pay when you stay
$177 nightly
$201 total
Nov 3 - Nov 4
Total with taxes and fees
8.8/10 Excellent! (3,790 reviews)
"Amazing place will be back staff was grate"
Reviewed on Oct 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.
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 cyclone_trudy
Osceola Heritage Park
7.8/10 (3,681 reviews)
Catch an event at Osceola Heritage Park during your trip to Kissimmee. Amble around this family-friendly area's seaside and enjoy its top-notch restaurants.
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
$27
per adult
92% of travellers recommend
Universal Orlando Resort Express Passes
$138
per traveler
80% of travellers recommend
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