Windsor Hills Resort vacation rentals
Family-friendly luxury just 2 miles from Walt Disney World.
- 2 mi
- To Disney
- Closest
- Resort we rent
- 3–6
- Bedrooms
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.
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
Available homes
Featured 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 the resorts compare
Every one of these is a gated community within a short drive of the parks. Here is how they differ — select one to see its homes.
- Paradise Palms Resort5 miCompact and best-priced. Tiki bar and cinema room.4–6 bedrooms
- Windsor Island7 miNewest Windsor community, lazy river, near-new villas.4–9 bedrooms
- Solara Resort6 miFlowRider surf simulator and eSports lounge. Teen-proof.4–10 bedrooms
- Windsor at Westside4 miOur best hand-painted themed bedrooms, short park run.4–9 bedrooms
- Storey Lake Resort4 miLakeside with a lazy river and kayaks. Great townhome value.3–9 bedrooms
- ChampionsGate8 miTwo clubhouses, two Norman courses, Publix at the gate.4–15 bedrooms
- Encore Resort5 miHotel-style concierge, restaurant and AquaPark.5–13 bedrooms
- Windsor Hills Resort2 miClosest to Disney. Cinema, zero-entry pool, mature and quiet.3–6 bedrooms
- Reunion Resort6 miThree golf courses, water park and true mansions.3–15 bedrooms
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