Luxury Vacation Homes in Orlando
Six bedrooms and up, each with a private pool, home cinema and games room
A luxury vacation home for rent in Orlando, Florida, as we define it here, means six or more bedrooms with a private pool, a home cinema and a games room, inside a gated resort community roughly 15 to 20 minutes from Walt Disney World. The whole house is yours, and it is booked direct with the local manager.
Right now that is 99 homes across ChampionsGate, Encore Resort, Reunion Resort, Storey Lake Resort, Windsor Hills Resort, Windsor Island and Windsor at Westside, sleeps 12 to 62.
Luxury means something specific on this page: at least six bedrooms, a pool belonging to the home rather than the resort, a room built for films and a room built for games. A home qualifies on what it has, not on how it photographs — which is why this set is narrower than a filter on bedrooms alone would give you.
Homes at this size cluster in the bigger resort communities. Many of these homes are at Reunion, with golf, a water park and its own restaurants inside the gates, and the rest are spread across the other Kissimmee and Davenport resorts. If the group is larger again, our ten bedroom homes go further up the scale.
You book direct with the local team that looks after the house, so the extras are arranged rather than ordered from a menu: groups in a home this size often want a chef cooking dinner at the house on arrival night instead of taking everyone back out to a restaurant. Many of these homes sit on the Kissimmee side of the parks, and the Kissimmee vacation homes page is the wider view of those resorts.
Luxury homes that meet the bar
24 properties found
Who these homes are for
Mostly groups that would otherwise be split across a row of hotel rooms. Multi-generational trips are the classic case: grandparents, parents and children under one roof, with a kitchen big enough to cook for everyone and a pool deck where the adults can sit while the children swim. The cinema and games room matter more than they sound, because they give a big group somewhere to gather after the parks without anyone having to go back out.
Family reunions, milestone birthdays and two or three families travelling together are the other usual reasons. Some of these homes also have themed bedrooms for children, which is worth checking in each listing's photos if you are bringing young ones. If your headcount is higher again, our largest homes, which sleep 20 and more, or two neighbouring homes in the same resort, are the usual answer.
Choosing the right home: a quick checklist
- Count beds, not bedrooms. The sleeps figure on each listing includes bunk beds and sofa beds, so work out how many adults need a proper bed of their own.
- If anyone in the group finds stairs difficult, ask us which homes have a bedroom on the ground floor before you book.
- Decide on pool heating up front. It is an optional extra, and between roughly November and March it is the difference between a pool you use and one you look at.
- Choose the resort for what is inside the gates as well as the house. Golf, a water park and on-site restaurants vary by community, and each resort page lists its own.
- Check the drive to the parks you will visit most, not just to Disney. Every resort page carries a distance table.
- Plan the arrival day. Check-in is 4:00 PM and check-out is 10:00 AM, which leaves time for a grocery stop on the way in from the airport.
Why book direct with us
Booking platforms add their own service fee on top of the nightly rate. Booking direct with us removes it, which on a home this size is real money. When you book well ahead you pay a deposit to hold the dates and the balance nearer your arrival, rather than the whole stay at once.
You also deal with the people who look after the house. Karen, Yvonne and Amalia know these homes individually, so a question like which one has a ground-floor bedroom or sits closest to the clubhouse gets an answer from someone who knows the house. There is more on how it works on our book direct page.
Common questions
What counts as a luxury vacation home in Orlando?
On this page it is a measurable bar rather than a mood: six bedrooms or more, a private pool belonging to the home, a home cinema and a games room. Plenty of handsome villas miss one of those and are left out, which is the point of setting the bar in public.
Do all of these homes have a private pool?
Yes — a private pool is part of the definition, so a home without one never appears here, and most have a spa or hot tub beside it. Pool heating is an optional extra you add at booking, worth having between roughly November and March when Florida evenings turn cool.
How far are these luxury homes from Walt Disney World?
Roughly fifteen to twenty minutes by car from the Disney gates, depending which resort the home sits in. Each resort page carries its own measured distance table, and the closest community we rent in is under three miles out. Every home has free parking, and driving is how most guests reach the parks.
Are the homes inside gated resort communities?
All of them. Each house sits inside a gated community with a controlled entrance, and access to the resort's own facilities comes with the stay rather than being bought separately — typically a pool complex, a fitness centre, and on-site dining where the community has it.
Can you arrange a private chef or a grocery delivery before we arrive?
A chef, yes: our Guest Services guides cover the partner who plans the menu, shops, cooks in your villa kitchen, serves at the table and clears up afterwards, booked directly with them. Groceries are down to you — most guests either order a supermarket delivery to the house or stop on the way in from the airport.
What time is check-in and check-out?
Standard check-in is 4:00 PM and check-out is 10:00 AM. Early check-in and late check-out can sometimes be arranged, depending on whether the home has guests leaving or arriving that day, so ask when you book rather than on the morning.
How far ahead should we book a luxury home in Orlando?
As early as you can for school holidays, Christmas and Easter. Homes that meet this bar are a small share of what is available in Orlando, and a large group usually needs one particular size, so the right house for those weeks tends to go first. Outside the peak weeks there is more room to wait.
Send us your dates and your headcount and we will tell you which of these houses actually fits your group, and which does not. If the six-bedroom floor is more than you need, our Orlando villas page opens the search back up to everything we manage, from the smaller pool homes upwards.