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Windsor Hills Resort vacation rentals

Family-friendly luxury just 2 miles from Walt Disney World.

20
Homes
3–6
Bedrooms
2 mi
To Disney

Windsor Hills Resort is a gated community in Kissimmee, Florida, about two miles from Walt Disney World — the closest resort we rent in — with a 140,000-gallon heated lagoon pool, a water park and a 48-seat cinema in the clubhouse. We manage 20 homes at Windsor Hills Resort from 3 to 6 bedrooms, sleeping 6 to 17, every one with a private pool, booked direct with the family that looks after them.

20
Homes we manage
3–6
Bedrooms
6–17
Sleeps
20
With a private pool
14
With a games room
8
With a home cinema

The close one

Two miles from the gates, and it shows

Windsor Hills is the closest gated resort to Walt Disney World that we rent in — close enough that families regularly go back to the villa for an afternoon swim and return to the park for fireworks. The community is older than Encore or Solara, and that means shade: mature palms, established landscaping and a settled, quiet feel.

The clubhouse carries a zero-entry pool with a water slide, a 58-seat cinema, an arcade and tennis courts. Homes are three to six bedrooms plus condos, which makes it the value pick for a single family that wants proximity above all.

Why guests choose it

  • Unbeatable proximity

    Two miles to the Disney gates — five to eight minutes door to car park.

  • 58-seat cinema

    Free movie screenings in the clubhouse most evenings.

  • Mature, quiet community

    Shaded streets and established landscaping, not a new build site.

Inside the resort

What is on site at Windsor Hills Resort

What is actually on site

Windsor Hills exists for one reason above all others: it is about as close to Walt Disney World as a vacation rental community gets. If your week is mostly park days, that proximity is worth more than any single amenity, because it is the difference between going back to the house for an afternoon nap and not bothering.

The facilities are still substantial. The clubhouse holds a staffed welcome centre, a fitness centre, a games room, a 48-seat high-definition cinema, changing facilities and the Marketplace & Grill. Outside there is a 140,000-gallon zero-entry lagoon pool heated year round, a large hot tub, and a water park with dueling slides and a splash zone. Homes here are the smaller end of our range, three to six bedrooms — see our 3 bedroom vacation homes and 6 bedroom vacation homes for how those sizes compare.

Pool and water park

  • 140,000-gallon lagoon pool

    Zero-entry and heated year round, open 8am to 10pm, 365 days a year.

  • Large hot tub

    Beside the main pool.

  • Sir Windsor's AquaVenture

    The water park: two large dueling slides, two smaller slides and a giant splash pad. Open 10am to 8pm daily.

The clubhouse

Open 8am to 10pm.

  • 48-seat cinema

    High definition, with plush seating — a proper screening room.

  • Fitness centre

    Described by the resort as state of the art.

  • Games room

    Indoors at the clubhouse.

  • Staffed welcome centre

    Front desk for arrivals and questions.

  • Marketplace & Grill

    Essentials, made-to-order food and drinks. Open 10am to 8pm.

  • Shower and changing facilities

    Useful on a departure day after checkout.

Sport and outdoors

  • Three playgrounds

    Fenced, with slides, tunnels and chess sets, spread across the resort.

  • Basketball

    Courts on site.

  • Pickleball

    Court on site.

  • Putting green

    For a short game without leaving the resort.

  • Community charcoal grills

    Alongside the recreation areas.

Resort amenities

  • Just 2 miles from Disney's main gates
  • Lagoon pool, waterslide & splash pad
  • Clubhouse with movie theater & fitness center
  • 2 to 6 bedroom villas and condos
  • Private screened pools and patios
  • Gated community with 24/7 security

Location

The shortest park commute in the area

Off Old Lake Wilson Road, minutes from the Disney's Animal Kingdom side of the resort and the US-192 shops.

Walt Disney World
2 mi · 6 min
Universal Orlando
15 mi · 21 min
SeaWorld Orlando
11 mi · 16 min
Orlando Int'l (MCO)
23 mi · 28 min
Disney Springs
approx. 7 mi · 13 min
Orlando International Airport (MCO)
approx. 23 mi · 30 min
LEGOLAND Florida
approx. 33 mi · 45 min
Publix supermarket
approx. 1 mi · 3 min
AdventHealth Celebration hospital
approx. 7 mi · 12 min

Know before you go

Practical details for Windsor Hills Resort

Gated entry
Gated community with a staffed welcome centreYour name goes on the gate list before arrival — we handle that when your booking is confirmed.
Pool hours
8:00am–10:00pm, 365 days a yearHeated year round.
Water park hours
10:00am–8:00pm daily
Clubhouse hours
8:00am–10:00pm
Marketplace & Grill hours
10:00am–8:00pm
Amenity access
Included with the stayClubhouse, pool and water park come with the home rather than as paid add-ons.
Parking
Free, at the homeDriveway and garage space varies by home.
Location
Kissimmee, FL — the closest of our resorts to Walt Disney World

Available homes

Featured homes at Windsor Hills Resort

View all 20 homes →
View all 20 homes at Windsor Hills Resort

Filter by bedrooms, guests, pool and dates on the full listing.

Inside the resort

17 photos — select any to enlarge.

Nearby

Two miles from Disney, five from everything else

  • Dining

    US-192 restaurant strip

    Five minutes: family buffets, steak, Mexican and Italian.

  • Shopping

    Orlando Vineland Premium Outlets

    Twelve minutes for the designer outlet run.

  • Attraction

    Disney Springs

    Twelve minutes, and the easiest evening out with kids.

  • Groceries

    Publix on Rolling Oaks

    Four minutes for the arrival-day shop.

Windsor Hills questions we're asked most

Is Windsor Hills really the closest resort to Disney?

Of the communities we rent in, yes — around two miles to the Walt Disney World boundary, five to eight minutes to a park car park. Families here typically do a mid-afternoon swim break.

Are the homes older than at Encore or Solara?

The community was built in the mid-2000s, so architecture is Mediterranean rather than contemporary. Our own Windsor Hills homes are refurbished and inspected between every stay.

Can we see Disney fireworks from the resort?

From some upper-floor windows and the pool deck on clear nights, yes — but we never promise a specific view. Ask us and we'll tell you honestly which homes have the best angle.

Is it good for a single family rather than a group?

It's our top recommendation for one family of six to twelve. Three to six-bedroom homes, short park runs and a clubhouse that keeps kids busy on rest days.

How close is Windsor Hills Resort to Disney World?

About two miles, usually five to ten minutes by car — it is the closest resort community we rent in. That proximity is the main reason people choose it: going back to the house midday for a swim or a nap stops being a chore and becomes part of the plan.

Does Windsor Hills Resort have a water park?

Yes — Sir Windsor's AquaVenture, with two large dueling slides, two smaller slides and a giant splash pad. It runs 10am to 8pm daily, separate from the main lagoon pool, which is open 8am to 10pm every day of the year.

Is the pool at Windsor Hills heated?

Yes. The 140,000-gallon zero-entry lagoon pool is heated year round and open 8am to 10pm, 365 days a year, with a large hot tub beside it. That is separate from any private pool at your home, which has its own optional heating charge.

Is there a cinema at Windsor Hills Resort?

There is a 48-seat high-definition movie theatre in the clubhouse with plush seating, alongside the games room, the fitness centre and the Marketplace & Grill. It is part of the clubhouse rather than a paid extra, which makes a wet afternoon much easier to fill.

What is included with a Windsor Hills vacation home rental?

The clubhouse, the heated lagoon pool, the water park, the fitness centre, the games room, the cinema, the playgrounds and the sports courts all come with the stay. Food from the Marketplace & Grill and anything you rent are charged separately.

What size homes are at Windsor Hills Resort?

Our Windsor Hills homes run from three to six bedrooms, which makes it the resort for a single family or two families travelling together rather than a large group. If you need more space than that, ChampionsGate and Reunion carry our biggest properties.

Are there playgrounds at Windsor Hills Resort?

Three of them, spread across the resort and fenced for safety, with slides, tunnels and chess sets. Along with basketball, a pickleball court and a putting green, they cover the gap between park days without anyone needing to get in the car.

Is there somewhere to eat at Windsor Hills Resort?

The Marketplace & Grill sits at the centre of the clubhouse and serves made-to-order food and drinks alongside essentials and resort merchandise, open 10am to 8pm. For a full grocery shop the nearest Publix is about a mile away.

Is Windsor Hills Resort gated?

Yes, and the clubhouse has a staffed welcome centre for arrivals. Your party's name goes on the gate list before you arrive — we arrange that when your booking is confirmed, so there is nothing for you to organise on the day.

Does Windsor Hills Resort have a gym?

Yes, a fitness centre in the clubhouse, open with the rest of the building from 8am to 10pm. There is also a putting green, basketball and pickleball outside if you would rather exercise without a treadmill involved.

Book direct

Let's find your Windsor Hills home

Karen, Yvonne and Amalia know these homes personally. Tell us your dates and party size and we'll shortlist the right ones — no platform fees, flexible payments.

  • Transparent pricing — no hidden platform fees
  • Flexible payment plans on every booking
  • Homes inspected by us between each stay
  • One family, three names, always reachable

Windsor Hills Resort

Closest to Disney · cinema · zero-entry pool

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