Vacation your way. Florida all day.Kissimmee Vacation Rentals With Private Pools
More house for your money, resort communities with water parks, and Disney still only minutes away.
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 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.
Our two main Kissimmee communities are Windsor Hills, which is about two miles from Walt Disney World and the closest of anything we host, and Storey Lake, which has a lazy river and slides and suits groups with a wide age range.
Distances from our Kissimmee homes
Bar length is scaled to distanceDrive times vary with traffic
Drive times are typical and vary with traffic. Peak park arrival and departure hours add time in both directions.
Our Kissimmee homes
Every home is filterable by how many people you need to sleep, whether you want a private pool, and how close you want to be. All of them are managed by us, cleaned by our own teams and inspected before you arrive.
Getting here from the airport
$125 per vehicle from MCO to Kissimmee. Up to eight passengers, fuel and child seats included.
A family of six or seven with luggage needs the largest rideshare class, which costs substantially more than the standard fare and moves with demand — and at an airport, demand moves exactly when every flight lands. Our price is fixed when you book.
What is nearby
Our Kissimmee guide covers where to go, when to go and what things cost, and the things-to-do guides break down individual attractions with cost bands and practical detail.
Frequently asked 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 more space, and the resort communities here have stronger shared amenities than most Orlando neighbourhoods.
Which community is closest to Disney?
Windsor Hills, at roughly two miles. Nothing else we host is closer.
Are the resort amenities included?
Access to the community amenities is included with your stay at every community we host in. Some communities charge a separate resort fee for certain facilities; where that applies it is shown on the property page before you book, not at checkout.
Can we walk to anything?
Within the gated communities, yes — the clubhouse, pools and playgrounds. Outside them, Kissimmee is built for driving. Plan on a car or transfers.
Tell us the dates and the group
We will come back with the homes that genuinely fit, and say so if nothing does.
- Every enquiry reaches a person, not a queue
- Instant acknowledgement, then a real reply
- We tell you when something does not suit us
Ask about a stay
Dates, group size and what matters to you. We reply with what actually fits.
We have your dates
You will get an email with the homes that are genuinely free on those dates. If nothing fits we will say so rather than sending you a list of alternatives you did not ask for.
Back to the homepageRouted straight into our CRM on the Guest pipeline, tagged GUEST-ENQUIRY at creation. You get an automated acknowledgement immediately — a person follows it.