Kissimmee Holiday Homes

Compare 274 Kissimmee holiday homes and Airbnbs with private pools and full kitchens. Check rates and photos, then book the home that fits your trip

Check-in
Tue, 06 Oct
Check-out
Wed, 07 Oct
Rooms and Guests2 Guests, 1 room
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Check-in
Tue, 06 Oct
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Check-out
Wed, 07 Oct
Rooms and Guests2 Guests, 1 room
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Check-in
Tue, 06 Oct
-
Check-out
Wed, 07 Oct
Rooms and Guests2 Guests, 1 room
1Filter & Sort
View map
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7.6
Very good32 total reviews
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14.8 mi from City Center
Private PoolGame RoomMovie Theater
  • Private pool with game room
  • In-home movie theater
  • 8-bedroom villa for large groups
FromUS$ 268 /nightSelect

Kissimmee holiday homes offer more than just a place to sleep-they are designed for families and groups who want extra space, privacy, and resort-style amenities. From compact 3-bedroom townhomes to sprawling 8-bedroom villas, these rentals come with fully equipped kitchens, private pools, and separate living areas. Many properties sit within gated communities like Veranda Palms or Cumbrian Lakes, placing you minutes from Disney World, Gatorland, and SeaWorld. Budgets vary, but with nightly rates often starting under $150, these homes deliver more square footage and flexibility than a standard hotel room.

For travelers who prioritize entertainment, look at options like Margaritaville Cottages Orlando by Rentyl, which features an on-site waterpark, pool bar, and spa, or Sonoma Resort's 7-bedroom home with a private pool and wellness center. For a quieter retreat, Formosa Garden Pool Home offers a private pool and games room at a budget-friendly price. Popular areas to consider include Celebration, Reunion Resort, and the US-192 corridor, all within 10-15 km of major attractions. When booking, check for free cancellation, parking, and whether the pool is heated-especially during winter months. Top-rated properties like The Bear's Den Resort Orlando even include an infinity pool, waterpark, and multiple restaurants for a true all-in-one stay.