Historic Downtown Kissimmee Vacations
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Your Historic Downtown Kissimmee Vacation
With a tailor-made vacation package to Historic Downtown Kissimmee, you can spend less time planning and more time simply enjoying this interesting neighborhood. From its shopping to its dining, there's plenty to discover here. When it's time to explore the sights, you'll find loads of top attractions nearby including Osceola Heritage Park, Kissimmee Lakefront Park and Silver Spurs Arena. Visit one, two or more during your trip to Historic Downtown Kissimmee. Expedia will help you turn your dream Historic Downtown Kissimmee vacation into reality, whatever your travel plans or budget.
- Westgate Vacation Villas Resort
Aug 13 - Aug 19Westgate Vacation Villas Resort + Flight
Kissimmee6 nights8.2/10 - Very Good (1,975 reviews)"Loved this property, would stay again,"Reviewed June 8, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop - Westgate Town Center Resort
Jul 14 - Jul 23Westgate Town Center Resort + Flight
Kissimmee9 nights8.2/10 - Very Good (1,764 reviews)"Place was very nice and clean"Reviewed June 9, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop - Westgate Towers Resort
Jul 14 - Jul 23Westgate Towers Resort + Flight
Kissimmee9 nights8.6/10 - Excellent (1,005 reviews)"Always a great stay at westgate."Reviewed June 8, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop - Mission to Mars
Aug 17 - Aug 21Mission to Mars + Flight
Loughman4 nightsRoundtrip • Philadelphia (PHL) - Orlando (MCO)PHL - MCO • Nonstop MCO - TTN • Nonstop - Westgate Lakes Resort & Spa Universal Studios Area
Aug 13 - Aug 19Westgate Lakes Resort & Spa Universal Studios Area + Flight
Orlando6 nights8.4/10 - Very Good (6,567 reviews)"Super helpful staff! Clean rooms and in a great location!"Reviewed June 8, 2026Roundtrip • New York (EWR) - Orlando (MCO)EWR - MCO • 1 stop MCO - EWR • 1 stop
Where to stay in Historic Downtown Kissimmee
International Drive District
Adventure activities, iconic attractions, shopping and world-class dining destinations make this famous street one of Orlando’s most popular tourist attractions.
Historic Downtown Kissimmee Hotel Deals
Sheraton Vistana Resort Villas, Lake Buena Vista/Orlando
"Property was great having to pay extra to park kinda sucked."
Reviewed on Jun 9, 2026
DoubleTree by Hilton at the Entrance to Universal Orlando
"Room was nice and big and clean."
Reviewed on Jun 8, 2026
The Grove Resort & Water Park Orlando
"We had an issue with charges to our card and got told to fix it with our bank and yet the charges didn’t match up. We paid everything Friday when we checked in, they had a bunch of hidden fees and deposits that aren’t disclosed when booking, and a 18% gratuity on everything that you buy. And yet ..."
Reviewed on Jun 9, 2026
Discover the most popular places to visit in Historic Downtown Kissimmee
Kissimmee Lakefront Park
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 lively festivals in this family-friendly area.
Osceola County Clerk of the Court
After visiting Osceola County Clerk of the Court, make a plan to see the other sights and activities in Kissimmee. Discover the top-notch restaurants and lively festivals in this family-friendly area.
Bataan-Corregidor Memorial
You can find out about the history of Kissimmee when you stop by Bataan-Corregidor Memorial. Stroll along the lakeside or experience the entertainment choices in this family-friendly area.
Things to do
Universal Orlando Resort Express Passes
Orlando: Polynesian Fire Luau with Dinner and Live Show
