Kissimmee Holiday Homes from ฿2,250: Search Top Rental Houses in Kissimmee

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

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Our top choices for Kissimmee holiday homes

A decorative stone fountain with a twisted base, surrounded by vibrant red flowers and tropical foliage, set against a backdrop of a pool and palm trees.

1. Maple Leaf Inn & Suites

Kissimmee

Shaneka

฿2,250 total

includes taxes & fees

25 Oct - 26 Oct

2. Shake Shack Heated Pool & Hot Tub

Kissimmee

Keith

฿12,475 total

includes taxes & fees

27 Oct - 28 Oct

A large rectangular pool with a central island, surrounded by palm trees and lounge chairs.

3. NBA Dream Mansion 15br Luxury Villa w Pool

Kissimmee

฿48,100 total

includes taxes & fees

2 Nov - 3 Nov

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Top Kissimmee Hotel Reviews

Hilton Vacation Club Mystic Dunes Orlando

10/10 Excellent

"This property was immaculate. It all started with extremely friendly staff. Very welcoming. The amenities are unbelievable. Beautiful pools, golf course, a kids club and multiple activities. There's a beautiful restaurant, put a little on the pricey side. But it's very country, club Esque, the room was clean. The bed was very comfortable we were only there for 2 days but have could have stayed so many more. When i'm in the orlando area again, I will definitely be staying at this resort. comfortable"

Seasons Florida Resort

10/10 Excellent

"Very nice pool. Staff very friendly and helpful-gave good advice on eating nearby. Didn’t really miss breakfast but it would have been nice. Hotel really clean-the staff seems to really care about your stay. Very quiet, comfortable bed. I stayed two nights and had a very pleasant experience."