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Windsor at Westside Resort Home w/ Pool & Hot Tub

Family-friendly holiday home with fitness centre and indoor pool

Photo gallery for Windsor at Westside Resort Home w/ Pool & Hot Tub

Spill Over Hot Tub
Spacious And Elegant Living Room With Large Smart Tv
Games Room with Pool Table, Foosball and Big Screen TV
In-home movie theatre with massive projection screen.
Sports courts, lazy river, jacuzzi hot tub, and more - we've got it all at the Windsor at Westside resort!

Reviews

10 out of 10
Exceptional
8 bedrooms6 bathroomsSleeps 16375.4 sq m

Popular amenities

  • Pool
  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning

Explore the area

View map
Kissimmee, FL
  • Place, Northeast Regional Park
    ‪4 min drive‬
  • Place, Lake Davenport
    ‪4 min drive‬
  • Place, Highland Reserve Golf Club
    ‪7 min drive‬
  • Airport, Kissimmee, FL (ISM-Kissimmee Gateway)
    ‪32 min drive‬

Rooms & beds

8 bedrooms (sleeps 16)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 King Bed

Bedroom 4

1 Queen Bed

Bedroom 5

1 Queen Bed

Bedroom 6

2 Single Beds

Bedroom 7

2 Single Beds

Bedroom 8

1 King Bed

6 bathrooms

Bathroom 1

Bathtub · Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Bathroom 5

Toilet · Shower only

Bathroom 6

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Garden
Dining area

About this property

Windsor at Westside Resort Home w/ Pool & Hot Tub

Summary:

Welcome to this spacious 8-bedroom retreat in the gated Windsor at Westside Resort. Enjoy a private, garden-facing patio with a swimming pool, spillover hot tub, BBQ grill, shaded dining area, and sun loungers. Inside, unwind in the game room with foosball, billiards, and board games—or host a movie night in your very own home theatre featuring a large screen. Perfect for families and group getaways! Book your stay now!



The Space:

Your dream group getaway starts here! This spacious 8-bedroom, 6-bathroom home sleeps up to 16 guests and delivers fun at every turn — with a private pool, bubbling hot tub, game room, and even a home theater. Located in the sought-after Windsor at Westside Resort, you’ll enjoy luxury living, resort perks, and a prime location just minutes from Disney and Orlando’s top attractions.



Poolside Paradise:

• Private screened-in patio with swimming pool & jacuzzi-style spa

• No rear-facing neighbors for added peace and privacy

• Sun loungers for soaking up the rays

• Covered outdoor dining area with BBQ grill — perfect for alfresco meals



Game On & Movie Nights:

• Garage-turned-games room with pool table, foosball & board games

• Private home theater with large projector screen & cozy seating

• High-speed WiFi + Smart TVs with cable for all your streaming needs



Cook, Dine & Chill:

• Fully equipped kitchen with high-end appliances & oversized island

• Indoor dining table for 10 + island seating & outdoor dining area

• Open-concept living space with plush seating and a large Smart TV

• In-home laundry machines and central A/C for ultimate convenience



8 Bedrooms / 6 Bathrooms:

With four ensuite bathrooms and thoughtful bedroom layouts, everyone in your group can enjoy comfort and privacy.



Bedroom Breakdown:



First Floor

• Bedroom 1: King bed | Private ensuite bath (ideal for guests avoiding stairs)



Second Floor

• Bedroom 2: King bed | Ensuite

• Bedroom 3: Queen bed | Shared bath

• Bedroom 4: 2 Full beds | Shared bath

• Bedroom 5: King bed | Ensuite

• Bedroom 6: 2 Twin beds | Shared bath

• Bedroom 7: Queen bed | Shared bath

• Bedroom 8: King bed | Ensuite



Windsor at Westside Resort Amenities:

• 24/7 gated entrance with security guard

• Massive resort-style heated pool with shallow-entry access

• Lazy river, kids’ splash zone & water slide

• Outdoor hot tub & sundeck with loungers

• Tiki bar (TuCasa) with cocktails and snacks

• Full-service clubhouse with restaurant & lounge

• Fitness center, tennis & basketball courts

• Playground, arcade & sundries shop



Whether you're floating in the lazy river, grabbing a cocktail poolside, or taking a break in the private theater, this home has something for everyone. Plus, you're just a short drive to Disney, Universal, shopping, dining, and more.



Extras & Essentials:

• Free driveway parking + additional guest parking at the clubhouse

• Pet-friendly — bring your furry companions along!

• Complimentary resort access for all registered guests



Why Stay With Us?

We make family vacations easy and unforgettable. From stylish interiors to resort-level entertainment, this home is designed for comfort, connection, and fun.



Book your Orlando adventure today!



Guest Access:

Parking:

• Up to 2 vehicles can park in the driveway. There is additional parking at the clubhouse if needed. Please note: the garage is not available, and the resort's policy limits a maximum of 5 vehicles per residence.



Property Access:

• Guests will enter the community through a gate and the security guard.



Resort Access:

• You're provided with complimentary access to the Windsor at Westside Resort.

• Clubhouse is open daily from 9am - 9pm, year-round.



The Neighborhood:

Windsor at Westside is a gated vacation rental community close to Disney featuring an 8,000 sq. ft. clubhouse with the Tu Casa Bar & lounge, market & deli, video arcade, sundries shop & fitness center. There are multi sports courts, a resort style swimming pool, whirlpool spa, tiki bar, poolside cabanas, kids play zone, lazy river and more!



The home is in an ideal location, which offers easy access to the Disney World theme parks via World Dr N, Bueno Vista Dr (this route has tolls) or Westside Blvd and US-192 E (no tolls). Also, close by are many dining, shopping and entertainment options!



Getting Around:

Windsor at Westside Resort:

One of the most desired resort communities in all of Kissimmee area! This ideal location offers easy access to the Disney World theme parks via World Dr N, Bueno Vista Dr (this route has tolls) or Westside Blvd and US-192 E (no tolls). Also, close by are many dining, shopping and entertainment options!



Nearby Family Attractions:

• Walt Disney World ~ 10 miles.

• Magic Kingdom Park ~ 15 miles.

• EPCOT ~ 15 miles.

• Hollywood Studios ~ 10 miles.

• SeaWorld ~ 16 miles.

• Universal Studios ~ 25 miles.



Nearby Other Attractions:

• Highlands Reserve Golf Club ~ 3 miles.

• Lake Louisa State Park ~ 13 miles.

• Camping World Stadium ~ 32 miles.

• Orlando Science Center ~ 34 miles.

• Mennello Museum of American Art ~ 36 miles.



Other Things to Note:

• Please note that the fridge's ice maker is currently unavailable. However, for your convenience, a separate ice maker is provided on the kitchen counter.

• To help ensure a safe and trusted experience for all guests, ID verification may be required after booking.

• Please note that we do not provide washcloths. Please bring your own washcloths to make use of during your stay.



Additional Services:

• Pool and hot tub heating is an additional service that is not included in your booking price. It's an additional fee of $35/night per service and $60/night for both, which we provide upon request. Please note that heating service is available with a minimum stay of 2 nights. Feel free to reach out for more details.

• We offer mid-stay cleaning for reservations over 3 days in duration. This service is available for an extra fee and will need to be booked in advance.



Pet Friendly:

• A pet fee of $129/pet per stay will be added at the time of booking if the pet is added to the reservation. If no pet is declared during booking, we will collect the fee separately. Pets up to 70lbs are welcome.

• If you have more than one pet, please note that an extra fee of $129 per pet will also be collected after booking confirmation.



We're happy to deliver:

- Your BBQ comes with a complimentary full propane tank at check-in! Running low? Get a one-time refill for just $55 and keep the grill going!

- a "Pack 'N Play Crib" for $40 (one-time fee).

- a Highchair for $40 (one-time fee).



Interaction with Guests:

We work with a team of dedicated hospitality professionals who will assist us in providing you with 5-star quality service. Your recommendations and questions are important to us and we're here 24/7 to assist you. Please don't hesitate to reach out to us at any time.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
Dryer
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted
1. Parties, events and smoking/vaping are prohibited in or around our property and risk of a fine and/or a forfeiture of your full deposit. 2. Plea...

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts cash
On-site parties or group events are strictly prohibited
Long-term renters welcome
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Kissimmee

Located in Kissimmee, this holiday home is in the city centre. Mystic Dunes Golf Club and Reunion Resort Golf Course are worth checking out if an activity is on the agenda, while those in the mood for shopping can visit Old Town and Disney Springs™. Travelling with kids? Don't miss Walt Disney World® Resort and Disney's Animal Kingdom® Theme Park.
Map
Kissimmee, FL

What's nearby

  • Northeast Regional Park - 4 min drive - 3.1 km
  • Lake Davenport - 4 min drive - 3.1 km
  • Highland Reserve Golf Club - 7 min drive - 4.0 km
  • ChampionsGate Golf Club - 9 min drive - 8.1 km
  • Mystic Dunes Golf Club - 10 min drive - 10.8 km

Getting around

  • Kissimmee Station - 32 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 41 min drive

Restaurants

  • ‪Dutch Bros Coffee - ‬8 min drive
  • ‪McDonald's - ‬7 min drive
  • ‪7-Eleven - ‬4 min drive
  • ‪Chick-Fil-A - ‬11 min drive
  • ‪Twistee Treat Berry Town - ‬7 min drive

Frequently asked questions

Does Windsor at Westside Resort Home w/ Pool & Hot Tub have a pool?

Yes, this property has an indoor pool.

Is Windsor at Westside Resort Home w/ Pool & Hot Tub pet-friendly?

No, pets are not allowed at this property.

How much is parking at Windsor at Westside Resort Home w/ Pool & Hot Tub?

On-site parking is available at the property.

What time is check-in at Windsor at Westside Resort Home w/ Pool & Hot Tub?

Check-in begins at 4:00 PM.

What time is check-out at Windsor at Westside Resort Home w/ Pool & Hot Tub?

Checkout is at 10:00 AM.

Where is Windsor at Westside Resort Home w/ Pool & Hot Tub located?

This family-friendly holiday home is located in the city centre, 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).

About the host

Hosted by Upstay

Host profile image
We get it - travel needs have changed big time. You want a vibe, a neighborhood, a space that feels like home but without the hassle, and that's where we come in.

Since 2019, we’ve managed hundreds of vacation properties, in 4 different countries, and you can expect best-in-class hospitality from us. Before you arrive we’ll email you all you need to know, and our team is here for you day or night, with 24/7 support.

Welcome to Upstay.

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