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Windsor Hills Resort Vacation Rentals Near Disney

Stay Minutes from Disney with Resort Pools, Family Fun & More Space to Relax

19 stays availableNeighborhood

About Windsor Hills

Guest reviews for Windsor Hills: 5.0 average from 57 reviews across 15 of 19 stays
Windsor Hills Resort is a gated vacation community in Kissimmee, Florida, known for its family-friendly atmosphere and convenient location near Walt Disney World. Guests can enjoy resort-style amenities, including a lagoon-style pool, water slides, splash areas, sports courts, playgrounds, and recreation facilities. With shopping, dining, golf, and Orlando-area attractions nearby, Windsor Hills offers families a comfortable and convenient base for a Central Florida vacation.

Overview

Windsor Hills Resort in Kissimmee, Florida, is a popular choice for families looking to stay close to Walt Disney World. Choose from spacious vacation homes, villas, condos, and townhomes with access to resort-style amenities, pools, and recreation, all while enjoying the comfort, privacy, and convenience of a vacation rental near Orlando’s top attractions.

Things to do in Windsor Hills

Top experiences and activities around Windsor Hills.

  • Enjoy the Windsor Hills Water Park

    Spend the day at the resort’s lagoon-style pool, water slides, splash areas, and family-friendly water attractions—perfect for relaxing between Orlando theme park visits.

  • Play Sports & Enjoy Resort Recreation

    Stay active with basketball, tennis, pickleball, playgrounds, fitness facilities, and other recreational activities available throughout the Windsor Hills community.

  • Spend a Day at Walt Disney World

    Take advantage of Windsor Hills’ convenient Kissimmee location and enjoy Disney theme parks, character experiences, rides, dining, and entertainment before returning to the comfort of your vacation rental.

Nearby attractions in Windsor Hills

Landmarks and day trips close to Windsor Hills.

Show nearby attractions
  • Disney’s Animal Kingdom

    Explore immersive lands, wildlife experiences, thrilling rides, live entertainment, and family attractions at one of the closest Walt Disney World theme parks to Windsor Hills.

  • Disney’s Hollywood Studios

    Enjoy Star Wars: Galaxy’s Edge, Toy Story Land, exciting rides, live shows, character experiences, and movie-inspired entertainment.

  • Magic Kingdom Park

    Experience iconic Disney rides, Cinderella Castle, character encounters, parades, fireworks, and attractions for families of all ages.

  • Disney Springs

    Discover waterfront dining, shopping, live entertainment, and family-friendly experiences with no theme park ticket required.

Popular destinations near Windsor Hills

Popular places to base yourself near Windsor Hills.

Explore around Windsor Hills

Hand-picked destinations and regions worth considering near Windsor Hills.

Best time to visit Windsor Hills

When to plan your stay in Windsor Hills.

The best time to visit Windsor Hills is from October through April, when pleasant temperatures are ideal for Disney trips, resort pools, and outdoor activities. Spring and fall offer comfortable weather, while winter is especially popular for family vacations.
Local travel tips for Windsor Hills

Practical advice for your trip to Windsor Hills.

  • Plan Disney Days Around Peak Traffic

    Leave early for Walt Disney World, especially during holidays and school breaks. Planning park tickets, dining, and popular experiences in advance can help families make the most of each day.

  • Take Advantage of Resort Amenities

    Schedule a relaxing resort day between theme park visits. Enjoy the pool, water park, playgrounds, and recreation at Windsor Hills to give the family a break from busy Orlando attraction days.

Frequently asked questions

Common questions about Windsor Hills.

How close is Windsor Hills Resort to Walt Disney World?

Windsor Hills Resort is conveniently located near Walt Disney World in the Kissimmee area, making it a popular choice for families planning Disney vacations. Actual driving times vary by theme park, traffic, and time of day.

What types of vacation rentals are available at Windsor Hills Resort?

Windsor Hills vacation rentals include private pool homes, villas, condos, and townhomes. Options range from smaller family accommodations to spacious multi-bedroom homes for larger families and groups.

What amenities does Windsor Hills Resort offer?

Windsor Hills offers resort-style amenities that may include a lagoon-style swimming pool, water slides, splash areas, playgrounds, sports courts, fitness facilities, and other family recreation. Access may vary by rental.

Is Windsor Hills Resort good for families with children?

Yes. Windsor Hills is popular with families because of its proximity to Disney World, gated setting, vacation-home options, swimming facilities, playgrounds, and recreational amenities designed for different age groups.

Do Windsor Hills vacation rentals have private pools?

Many Windsor Hills vacation homes and townhomes feature private pools, while condos typically provide access to community swimming facilities. Check each property listing to confirm private-pool availability and other included amenities.

Make Windsor Hills Resort your family home base near Disney World. Enjoy spacious vacation homes, villas, and condos with resort-style pools, recreation, and plenty of room to relax. Stay close to Orlando’s theme parks, dining, and entertainment while enjoying the comfort and convenience of a private vacation rental.