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Splash fountain on the Celebration lakefront lined with palm trees under a summer sky

Orlando & Kissimmee · 11,578 licensed rentals

Kissimmee vacation rentals

Photo: Mx. Granger · CC0

US-192, also called Irlo Bronson Memorial Highway, is the spine of Kissimmee's vacation-home country. The west end runs up to the edge of the Walt Disney World property, and the side roads off it lead into gated communities built almost entirely for visitors: rows of pool homes and townhomes with screened lanais, clubhouses and resort pools. Historic downtown Kissimmee and Lake Tohopekaliga sit at the east end, where the lakefront park and its lighthouse look out over one of the best-known bass lakes in the state.

This is the place for a family that wants a private pool, a bedroom for every kid and a short drive to the parks each morning. Celebration, the planned town just off 192, adds a walkable downtown on a lake with shops and restaurants, and its quiet tree-lined streets have homes and condos of their own.

Things to do near your rental

  • Kissimmee Lakefront Park and fishing on Lake Tohopekaliga
  • Downtown Celebration and its lakeside promenade
  • Gatorland on Orange Blossom Trail, north of downtown Kissimmee
  • Airboat rides on the lakes and marshes south and east of town

Licensed by the state of Florida

11,578 Kissimmee vacation rentals

Every listing starts from an active state license. Owners who claim their listing add photos, rates and a direct booking link, and appear first.

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    Kissimmee rental questions

    Do Kissimmee vacation homes have private pools?

    Most of the single-family homes in the vacation communities off US-192 do, usually screened and often with a heater available for an added fee. Townhomes are more likely to share a community pool. Ask the owner about pool heat before you book a winter trip.