Kissimmee Vacation Rentals With Private Pools

Why stay in Kissimmee

Kissimmee is where most families end up once they have run the numbers. You get noticeably more square footage than in Orlando proper, the resort communities have amenities that genuinely compete with the parks for the children's attention, and you are still close enough that an afternoon nap back at the villa is realistic rather than theoretical.

It also has a life of its own beyond the parks — Old Town, the airboat operators out on the lakes and marshes, and some of the best value dining in Central Florida.

Drive times from our Kissimmee homes

Resort communities in Kissimmee

Storey Lake and Windsor Hills are our main Kissimmee communities. Both are gated, both have water features the children will not want to leave, and both are close enough to Disney that you can do a half day and come back.

What to do in Kissimmee

Airboats through the marshes, Old Town on a Saturday night, and lakes that most park-focused visitors never see.

Kissimmee questions

Is Kissimmee better value than Orlando?

Generally yes, for the same size of home — you are trading a few minutes of drive time for meaningful savings and usually more space.

Are the resort amenities included?

Yes. Access to the community's shared amenities — water parks, lazy rivers, pools, fitness centres and clubhouses — is included with your stay at no extra charge. A few communities issue amenity wristbands or parking passes on arrival; where that applies we send the details in your pre-arrival information.