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Gated Windsor at Westside · Family Retreat 8877

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A pool area with lounge chairs, umbrellas, and a water slide. - Gated Windsor at Westside · Family Retreat 8877 (Kissimmee)
A spacious lobby with a reception desk, seating area, and large windows. - Gated Windsor at Westside · Family Retreat 8877 (Kissimmee)
A beach volleyball court with palm trees and a clear sky. - Gated Windsor at Westside · Family Retreat 8877 (Kissimmee)
A gym with treadmills, weight machines, and dumbbells. - Gated Windsor at Westside · Family Retreat 8877 (Kissimmee)
A covered outdoor seating area with a lounge chair, a large planter, and a view of a body of water and greenery. - Gated Windsor at Westside · Family Retreat 8877 (Kissimmee)
You can look forward to an arcade/games room, laundry facilities and a gym at Gated Windsor at Westside · Family Retreat 8877. Guests can connect to free in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Pool
  • Kitchen
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Gym

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About this property

Gated Windsor at Westside · Family Retreat 8877

  • THE SPACE

    Welcome to your dream family getaway at the prestigious Windsor at Westside Resort. This fabulous 5-bedroom, 5.5-bathroom home sleeps up to 10 guests and combines the magic of Orlando with the comfort of your own private oasis, with a screened pool, a game room and two themed kids' bedrooms.

    Child Safety: The private pool is equipped with a removable CHILD SAFETY FENCE for added peace of mind.

    Game Room
    The garage has been transformed into a game room for endless entertainment, with a pool table and foosball.

    Main Floor
    The heart of the home is the bright and inviting open-plan ground floor. Relax in the spacious living room with a 60" HDTV, gather for meals in the dining area or prepare family feasts in the fully equipped kitchen.

    Also on this level is a serene master suite with a King bed and a luxurious ensuite bathroom with a beautiful bathtub.

    Step outside to your private, screened-in patio to splash in your own pool or relax on the sun loungers.

    Upstairs
    A cosy loft serves as a second living area, with a large sofa and a big TV for film nights.

    Kids will love the two themed bedrooms:
    • Avengers Room: two Twin beds in an action-packed setting
    • Mickey and Friends Room: two Twin beds in a cheerful setting

    Also upstairs:
    • King Bedroom
    • Queen Bedroom

    Sleeping Arrangements
    • Bedroom 1 (Master Suite, main floor): King
    • Bedroom 2: King
    • Bedroom 3: Queen
    • Bedroom 4 (Avengers): Two Twins
    • Bedroom 5 (Mickey and Friends): Two Twins

    GUEST ACCESS

    You will have exclusive access to the entire home, including the game room and your own private, screened-in pool, the perfect oasis for sunny Florida afternoons.

    Your stay also includes full, complimentary access to the first-class Windsor at Westside resort amenities:
    • 24-hour gated security
    • An extraordinary 5,000 sq. ft. clubhouse with lounge areas, a TV room, meeting rooms, a business centre and Wi-Fi
    • A massive, heated, zero-entry resort-style pool with a sun deck, a winding lazy river and thrilling waterslides
    • A children's water park and splash pad and a kids' playground
    • A community hot tub, a poolside tiki bar and shaded cabanas
    • A state-of-the-art fitness centre, an arcade and game room and a mini-golf course
    • Sand volleyball, basketball, tennis and multi-purpose sports courts, a football field and cornhole
    • A market and deli, a sundry shop, an on-site restaurant and an ATM
    • Concierge service and valet trash service
    • Waterfront lake access with a pier

    THE NEIGHBORHOOD

    Windsor at Westside is one of Orlando's most sought-after holiday communities, with 24-hour gated security and known for its incredible amenities and prime location. The community is beautifully maintained and even offers access to a serene lake via a small dock.

    You are just minutes away from the magic:
    • Walt Disney World: 8 minutes via the Disney west entrance
    • SeaWorld: 18 miles
    • Universal Studios: 22 miles
    • Orlando International Airport (MCO): 30.5 miles
    GETTING AROUND

    The home offers easy driving access to Orlando's major theme parks, shopping centers and dining destinations. We recommend having a vehicle for maximum flexibility. On-site parking is available.

    HOUSE RULES

    • Check-in is at 4:00 PM
    • Check-out is at 10:00 AM
    • Minimum age to book is 21

    • Towels, linens, hair dryers, an iron and an ironing board are provided
    • A starter pack of essentials is included
    • Washcloths are not provided

    • A Pack 'n Play and a high chair are available upon request

    • Pool heat is available for $30 + tax per night
    • Heat must be requested at least 2 days before check-in

    • Grill is available for $65 + tax per stay, including one propane tank
    • Grill must be requested before check-in

    • Please contact us for package delivery instructions

    • Concierge services are available, including Disney tickets and grocery shopping

    Pets - not allowed


    Please check your email for arrival instructions once the reservation process is complete.

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About the area

Located in Kissimmee, this holiday home is near theme parks and near a water park. ChampionsGate Golf Club and Mystic Dunes Golf Club are worth checking out if an activity is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Disney's Animal Kingdom® Theme Park. Travelling with kids? Don't miss Disney's Hollywood Studios® and Old Town. Take the opportunity to explore the area for water adventures such as swimming. Visit our Kissimmee travel guide
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Map
Kissimmee, FL

What's nearby

  • Northeast Regional Park
    5 min drive - 2.6 miles
  • Lake Davenport
    6 min drive - 2.8 miles
  • Four Corners FC
    7 min drive - 4.0 miles
  • ChampionsGate Golf Club
    8 min drive - 4.9 miles
  • Highland Reserve Golf Club
    8 min drive - 3.4 miles

Getting around

  • Kissimmee Station
    33 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway)
    42 min drive

Restaurants

  • McDonald's
    7 min drive
  • Twistee Treat Berry Town
    7 min drive
  • 7-Eleven
    4 min drive
  • Chick-Fil-A
    11 min drive
  • 7 Brew Coffee
    11 min drive

Frequently asked questions

Does Gated Windsor at Westside · Family Retreat 8877 have a pool?

Yes, this property has a pool. Pool types include heated pools.

Is Gated Windsor at Westside · Family Retreat 8877 pet-friendly?

No, pets are not allowed at this property.

How much is parking at Gated Windsor at Westside · Family Retreat 8877?

On-site parking is available at the property.

Where is Gated Windsor at Westside · Family Retreat 8877 located?

This family-friendly Kissimmee holiday home is within 3 mi (5 km) of Highland Reserve Golf Club and Lake Davenport. Surfari Water Park and Mighty Jungle Golf are also within 6 miles (10 km).

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Reviews

Gated Windsor at Westside · Family Retreat 8877 Reviews

10

Exceptional

10

Cleanliness

10

Location
Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome location, very secure.secured. Loved the kitchen very spacious for us to cook and hangout. Thanks you.
Stayed 4 nights in Jun 2025