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Our top choices for Osceola County holiday rentals
Aparthotel in Kissimmee
voco Kissimmee Orlando by IHG7.4 out of 10, Good, (1003)
"Place was clean, staff great, cozy very nice area swimming pool"
KRYSTLE
The price is Rp1.056.951
Rp1.580.476 total
includes taxes & fees
5 Jan - 6 Jan 2026
Aparthotel in Kissimmee
Enchanted Dreams7.8 out of 10, Good, (7)
"Very relaxing space. Clean environment. Coming back very soon "
Tanish
The price is Rp1.172.500
Rp2.471.463 total
includes taxes & fees
24 Dec - 25 Dec
The price is Rp905.958
Rp2.170.775 total
includes taxes & fees
24 Dec - 25 Dec
Condo resort in Kissimmee
Regal Oaks Resort Vacation Townhomes by IDILIQ8.4 out of 10, Very good, (3035)
"Hot tub was nice.
Mattresses were the best!!!!"
corey
The price is Rp2.419.543
Rp6.059.472 total
includes taxes & fees
5 Jan - 6 Jan 2026
Aparthotel in Kissimmee
Margaritaville Cottages Orlando by Rentyl8.8 out of 10, Excellent, (1753)
"Great place "
Lauren
The price is Rp3.338.623
Rp7.147.376 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Home in Kissimmee
Super Cool- Sleeps 17 Newly Built Near ParksThe price is Rp1.927.359
Rp6.917.558 total
includes taxes & fees
16 Jan - 17 Jan 2026
Cottage in Chatham Park
Upstay: Bright Family-friendly Retreat With PatioThe price is Rp1.509.930
Rp4.551.012 total
includes taxes & fees
8 Jan - 9 Jan 2026
Condo in Kissimmee
Vacation Village Orlando, Celebration8.6 out of 10, Excellent, (3115)
"Great place to stay"
Jose
The price is Rp1.658.250
Rp2.300.863 total
includes taxes & fees
24 Dec - 25 Dec
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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Top Osceola County Hotel Reviews
Magic Moment Resort & Kids Club, Dazzler Select by Wyndham
10/10 Excellent
Find out more about Osceola County
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