Quick answer
This Windsor Hills Orlando villa holiday is 7 nights in a four-bedroom home with its own screened pool. Windsor Hills Resort Orlando is about 2 miles from the western edge of Walt Disney World. Return flights from the UK and private airport transfers are included. Prices start from £849 per person in Economy, and October 2026 is the lowest-priced month. Party size and cabin change the fare. ATOL 10713 protected.
This is a one-base week. You unpack once and plan each day around the parks, the pool and the weather. Nothing in the suggested plan is pre-booked, so park days can move if a storm rolls in or the children need a lie-in.
The villa suits families and groups who value separate bedrooms and their own kitchen over hotel service. It suits less well anyone who would rather not drive, and anyone hoping for a beach on the doorstep. Tell us how many are travelling and their ages, and we will confirm the flights, transfers and villa together on one quote.
Why You'll Love It
Included
Not included
Day by Day
Land at Orlando International and clear immigration, then meet your private driver for the run to Windsor Hills in Kissimmee. At the gatehouse your details are checked before you continue to the villa. Pick up basics for breakfast, swim once, and aim for a local bedtime.
Start with Magic Kingdom. Be at the gates for opening to ride Space Mountain and Seven Dwarfs Mine Train before queues build. Head back to the villa in the heat of the afternoon, then return for the fireworks if energy allows.
A slow day after the first park. Stay by your own pool in the morning, then spend the afternoon at the clubhouse. A barbecue at the villa takes care of dinner.
The Wizarding World of Harry Potter is split between these two neighbouring parks. A park-to-park ticket is needed to ride the Hogwarts Express from one side to the other. Epic Universe is a separate park and needs its own ticket and day.
Choose EPCOT for Guardians of the Galaxy: Cosmic Rewind and the eleven country pavilions around World Showcase, or Hollywood Studios for Star Wars: Galaxy’s Edge and Toy Story Land. Both are a short drive from the resort. For a rest day instead, Disney Springs has free entry, with shops and restaurants along the water.
Pack up and leave the villa by the owner’s check-out time, then take your private transfer back to Orlando International. Check your flight time when you book. If the flight home is overnight, pack a change of clothes in your hand luggage.
Where You'll Stay
5-star hotel
You stay in a four-bedroom villa within Windsor Hills, a resort of privately owned homes in Kissimmee. The house has open-plan living and dining space, a fully equipped kitchen and a private screened pool with a spa, and the stay is self-catering. The community is gated, with a gatehouse staffed 24 hours a day, so only registered guests and residents drive in.
All prices are per person based on two adults sharing. Includes return flights and accommodation. Click any month to enquire.
| ✈ Flights | Return flights from UK included |
| 🧳 Baggage | 23kg checked baggage |
| 🏛 Hotel | 7 nights accommodation |
| 🚌 Transfers | Private airport transfers |
| ✈ Airport Taxes | All airport taxes included |
| 💳 Deposit | 30% per person to secure booking |
Windsor Hills Resort is at 2600 North Old Lake Wilson Road, and Orlando International Airport is 30 to 35 minutes away by road.
Check the resort name on any quote you compare. Windsor at Westside and Windsor Island are separate resorts, sold by other UK operators under similar names. For a different gated community, look at our villa holiday at Encore Resort at Reunion, or browse our Orlando villa holidays.
The included transfers cover the airport journeys only, and the resort does not run its own shuttle to the parks. Plan your daily transport before you travel, and car hire gives you the most freedom.
A full UK photocard licence is valid for driving in the US. The FCDO says a 1949 international driving permit may also be needed, and you can only buy one in the UK. Without a car, taxis and rideshare apps reach the Disney parks quickly, though fares add up across several park days. Our guide to Orlando villas with flights from the UK compares transport by area.
The shared facilities are grouped around the resort clubhouse.
| Months | Average high | Rain | Price level |
|---|---|---|---|
| October–November | 29°C falling to 26°C | Drying out | Lowest. |
| December–February | 22–24°C, nights near 10°C | Low | High in January, mid in December and February. |
| March–May | 26–31°C | Moderate | High in March and April, lower in May. |
| June–September | 32–33°C | Wettest, with afternoon storms | High in July and August. |
Temperatures are Orlando's 1991–2020 averages from NOAA. The Atlantic hurricane season runs from June to November, so pick insurance that covers weather disruption. In midwinter an unheated pool feels chilly, so October, November and May give the best mix of warm water and lower prices.
The non-stop flight from the UK to Orlando takes about 9½ to 10 hours, and Florida is normally five hours behind the UK. Keep the first full day easy. Seven nights then fits four park days with pool days between them. Our Orlando planner for families helps match parks to children's ages.
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