A pathway through a park with Spanish moss hanging from trees and a body of water in the background.

Search Vacation Homes in Kissimmee

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Kissimmee vacation homes

Outdoor pool

Maple Leaf Inn & Suites

Maple Leaf Inn & Suites
2.5 star property
Kissimmee
6.8 out of 10, (71 reviews)
"The room was clean and the staff was okay "
United States
Shaneka
The price is ₩89,355
₩101,420 total
includes taxes & fees
Jul 19 - Jul 20
Maple Leaf Inn & Suites
Lobby sitting area

The Berkley, Orlando

The Berkley, Orlando
4.0 star property
Kissimmee
9.6 out of 10, Exceptional, (2,299 reviews)
"Truly enjoyed our stay! The hotel was clean and the room was impressive. The pool was nice and resort itself was quiet and relaxing. We would definitely stay again."
United States
Mitchell
The price is ₩196,242
₩237,529 total
includes taxes & fees
Jul 19 - Jul 20
The Berkley, Orlando
6 bedrooms, desk, Internet

Upstay - New Build - Resort Home w Pool Hot Tub

Upstay - New Build - Resort Home w Pool Hot Tub
3.0 star property
Kissimmee
8.0 out of 10, Very Good, (1 review)
"Friendly and very beautiful complex."
United States
Donna
The price is ₩602,696
₩1,039,045 total
includes taxes & fees
Jul 16 - Jul 17
Upstay - New Build - Resort Home w Pool Hot Tub
Front of property

Disney Area Home | Pool · Spa · Game Room | 5BR Sleeps 14

Disney Area Home | Pool · Spa · Game Room | 5BR Sleeps 14
4.5 star property
Lindfields
The price is ₩363,290
₩741,998 total
includes taxes & fees
Jul 21 - Jul 22
Disney Area Home | Pool · Spa · Game Room | 5BR Sleeps 14
House | 6 bedrooms

Champions Gate Luxury 6br-private Pool

Champions Gate Luxury 6br-private Pool
2.0 star property
Kissimmee
The price is ₩397,729
₩1,237,745 total
includes taxes & fees
Aug 11 - Aug 12
Champions Gate Luxury 6br-private Pool
House, 5 Bedrooms, Private Pool, Lakeside | Exterior

5BR Villa Private Pool & Game Room

5BR Villa Private Pool & Game Room
4.0 star property
Lake Berkley
6.0 out of 10, (1 review)
"We had several problems. The owner uses a management company & they were a nightmare to deal with."
United States
joseph
The price is ₩324,115
₩927,251 total
includes taxes & fees
Jul 20 - Jul 21
5BR Villa Private Pool & Game Room
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Kissimmee Hotel Reviews

Holiday Inn Club Vacations at Orange Lake Resort by IHG

Holiday Inn Club Vacations at Orange Lake Resort by IHG

8/10 Good
"Nice pools but not enough information to the amenities. All and all I love the place."
holee 2-night trip
Posted 1 hour ago
Holiday Inn Club Vacations at Orange Lake Resort by IHG

Find out more about Kissimmee

Kissimmee Vacation Homes information

Number of reviews
2,300
Accommodation
4832 Vacation Homes
Lowest Price
₩101,420
Highest Price
₩1,237,745