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Upstay: Spacious 8BR Family Home w Pool & Hot Tub

Photo gallery for Upstay: Spacious 8BR Family Home w Pool & Hot Tub

Spill Over Hot Tub
Spacious And Elegant Living Room With Large Smart Tv
In-house games room with foosball, billiards 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!
8 bedrooms6 bathroomsSleeps 16375.4 sq m

Popular amenities

  • Parking available
  • Dryer
  • Washer
  • Hot tub
  • Outdoor space
  • Barbecue grill

Explore the area

Map
Kissimmee, Florida
  • ChampionsGate Golf Club
    ‪10 min drive‬
  • Mystic Dunes Golf Club
    ‪13 min drive‬
  • Disney's Animal Kingdom® Theme Park
    ‪19 min drive‬
  • Kissimmee, FL (ISM-Kissimmee Gateway)
    ‪41 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

Upstay: Spacious 8BR Family Home w Pool & Hot Tub

Summary:
Upstay welcomes you 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:
Home Highlights:
• 8 bedrooms, 6 bathrooms (4 en suites)
• Sleeps up to 16 guests (10 beds total)
• Private screened-in patio with pool, jacuzzi & BBQ
• Games room with pool table, foosball & board games
• In-home theater with large projector screen
• Fully equipped kitchen with high-end appliances
• Dining for 10 + kitchen island & patio seating
• Smart TVs with cable & high-speed WiFi
• In-home laundry, central A/C & free parking
• Enjoy complimentary access to resort amenities

Planning a group trip or big family getaway? This pet-friendly home comfortably hosts up to 16 guests and is packed with fun from top to bottom. But first, let’s talk location. This beautiful property sits within the secure, family-friendly Windsor at Westside Resort—just a short drive from Disney and all the best Orlando attractions.

As a guest, you'll enjoy full access to the resort's incredible amenities: a lakefront pier with scenic views, a massive resort-style pool, concierge services, and a splash zone and water playground that the kids will absolutely love. Want to unwind? Sip a cocktail from the TuCasa Tiki Bar while you stretch out on the sundeck—or float your cares away in the lazy river. There’s also a fully equipped fitness center, beach volleyball, and sports courts if you’re feeling competitive.

Back at the house, you’ll love your own private backyard oasis. The screened-in patio offers a pool with no rear-facing neighbors for added privacy, a bubbling jacuzzi-style spa, sun loungers, and a shaded dining space complete with a BBQ grill—perfect for poolside meals.

Step inside and keep the fun going in the garage-turned-games room, featuring a pool table, foosball, board games, and puzzles for all ages. Don’t worry about the garage space—we’ve got ample parking in the driveway, and any extras can easily be accommodated at the clubhouse.

The home’s main level features an open-concept kitchen and living area. You’ll love the oversized island for prepping meals, chatting with the crew, or laying out snacks buffet-style. With tons of storage, counter space, and all the kitchen essentials, mealtime is a breeze.

Head upstairs for even more entertainment in your private home theater, complete with a large projector screen and comfy seating. All bedrooms are located on the upper floor—except for one convenient ground-floor master suite with a king bed and ensuite bath, ideal for guests who prefer to avoid stairs.

Whether you’re in the mood to explore or just relax, this vibrant home is set up for memory-making moments. Bring the whole crew and get ready for a stay packed with comfort, fun, and sunshine. Let your Orlando adventure begin!

Windsor at Westside Resort Features:
• 24hr gated entrance with security guard
• Clubhouse with licensed restaurant and lounge
• Lazy river for floating
• Resort-style heated pool with shallow-entry
• Children's splash zone with waterslide
• Outdoor jacuzzi hot tub
• Tiki bar
• State-of-the-art fitness center
• Children's playground
• Video arcade
• Market and Deli/Sundries Shop
• Tennis/Basketball court

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.

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:
*IMPORTANT NOTICE *
•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.

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:
• Pets up to 70lbs. are very welcome at our home. The pet fee is $129/animal (one-time fee).

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).

Quality Assurance:
• Your wellbeing is our top priority. We have built upon our foundation of pre-existing high cleaning standards with additional COVID-19 specific recommendations from the WHO, CDC and Canadian Public Health Agency guidelines.

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.

Property manager

Upstay

Languages

English

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washer
Dryer
Air conditioning

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House Rules

Check in after 4:00 PM
Minimum age to rent: 18
Check out before 11:00 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. ChampionsGate Golf Club and Mystic Dunes Golf Club 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™. Check out an event or a game at ESPN Wide World of Sports Complex, and consider making time for Walt Disney World® Resort, a top attraction not to be missed.
Map
Kissimmee, Florida

What's nearby

  • Highland Reserve Golf Club - 7 min drive - 4.3 km
  • ChampionsGate Golf Club - 10 min drive - 7.5 km
  • Mystic Dunes Golf Club - 13 min drive - 10.2 km
  • Reunion Resort Golf Course - 17 min drive - 10.5 km
  • Disney's Animal Kingdom® Theme Park - 19 min drive - 16.8 km

Getting around

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

Restaurants

  • ‪McDonald's - ‬8 min drive
  • ‪Culver's - ‬7 min drive
  • ‪Taco Bell - ‬7 min drive
  • ‪Best of British Cafe - ‬7 min drive
  • ‪Denny's - ‬8 min drive

Frequently asked questions

Does Upstay: Spacious 8BR Family Home w Pool & Hot Tub have a pool?

Yes, this property has an indoor pool.

Is Upstay: Spacious 8BR Family Home w Pool & Hot Tub pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Upstay: Spacious 8BR Family Home w Pool & Hot Tub?

Check-in begins at 4:00 PM.

What time is check-out at Upstay: Spacious 8BR Family Home w Pool & Hot Tub?

Checkout is at 11:00 AM.

Where is Upstay: Spacious 8BR Family Home w Pool & Hot Tub located?

Located in the heart of Kissimmee, this holiday home is 2.5 mi (4.1 km) from Highland Reserve Golf Club and 2.6 mi (4.3 km) from Lake Davenport. Northeast Regional Park and Surfari Water Park are also within 6 miles (10 km).

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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.

Languages:

English