Skip to content
Upstay

Choose your stay

Book directly with Upstay.

Disney Getaway w Pool, Hot Tub, Theater & Games

Disney Getaway w Pool, Hot Tub, Theater & Games

Kissimmee, Florida4.20 (32)
8 bedrooms · 11 beds · 6 bathrooms · Sleeps 16
HouseHot Tub

Where you’ll sleep

Queen
Bedroom 1
King
Bedroom 2
Queen
Bedroom 3
King
Bedroom 4
2x Twin
Bedroom 5
2x Twin
Bedroom 6
2x Twin
Bedroom 7
King
Bedroom 8

Escape to Orlando in this spectacular 8-bedroom vacation home, perfect for families and groups! Sleeps 16 and features a sparkling pool, hot tub, BBQ, pool table, foosball, and private movie theater. Enjoy Windsor at Westside Resort amenities including a resort pool, water park, and clubhouse.

About this property

Poolside Paradise
• Private screened-in pool and hot tub
• Optional pool and hot tub heating
• Removable pool safety fence
• Spacious patio with loungers
• Outdoor dining area
• BBQ grill
• Inflatable pool slide for kids

Gather, Relax & Play
• Open-concept kitchen, living, and dining area
• Fully equipped kitchen with stainless-steel appliances
• Granite countertops and ample storage
• Dining table seats 10
• Kitchen island seats 4
• Smart TV with cable and Netflix
• High-speed Wi-Fi and central A/C
• Private 135" movie theater
• Games room with pool table, and foosball
• In-home laundry and free onsite parking

Rest & Recharge
• Bedroom 1: King bed, ceiling fan with light, bedside lamps, TV with cabinet, ensuite bathroom with walk-in shower and bathtub
• Bedroom 2: King bed, ceiling fan, quality bedding, bedside lamp and cabinet, TV with cabinet, ensuite bathroom
• Bedroom 3: King bed, ceiling fan, quality bedding, bedside lamp and cabinet, TV with cabinet, ensuite bathroom
• Bedroom 4: Blue-themed Queen bedroom, ceiling fan, quality bedding, bedside lamp and cabinet, TV with cabinet, ensuite bathroom
• Bedroom 5: Purple-themed Queen bedroom, ceiling fan, quality bedding, bedside lamp and cabinet, TV with cabinet, ensuite bathroom
• Bedroom 6: Frozen-themed bedroom with two single beds and ceiling fan
• Bedroom 7: Star Wars-themed bedroom with two single beds and ceiling fan
• Bedroom 8: Two single beds, center lamp, and ceiling fan

Windsor Resort Experience
• 24-hour gated entrance with security
• Resort-style pool, hot tub, and lazy river
• Children's water playground, waterslides, arcade, and activities
• Clubhouse, fitness center, Tiki bar, and sports courts

The area

Windsor at Westside is a gated resort community conveniently located near Orlando’s major theme parks, restaurants, shopping, and entertainment. The resort offers extensive on-site amenities, making it an ideal base for families and groups.

Nearby Attractions
• Windsor at Westside Resort amenities ~ 2 km
• Northeast Regional Park ~ 2.4 km
• Lake Davenport ~ 2.7 km
• Four Corners ~ 4.7 km
• Highland Reserve Golf Club ~ 6.2 km

Windsor at Westside is perfectly located to give you easy access in to the back entrance of Disney World via Black Lake Road followed by Sherbeth Road, so you will experience very minimal traffic. Close to shops, supermarkets (publix) and restaurants it's a great location to explore all the Orlando theme park attractions.

Other Family Attractions
• Hollywood Studios ~ 16.1 km
• Lake Louisa State Park ~ 20.9 km
• Magic Kingdom Park ~ 24.1 km
• EPCOT ~ 24.1 km
• SeaWorld ~ 25.7 km
• Universal Studios ~ 40.2 km
• Camping World Stadium ~ 51.5 km
• Orlando Science Center ~ 54.7 km
• Mennello Museum of American Art ~ 57.9 km

Airport: Orlando International Airport ~ 48.3 km (30 miles).

Notes from your host

• For a smooth and secure check-in experience, all guests may be required to complete ID and Enso Boarding Pass verification before arrival. Check-in instructions will be shared once verification is completed. Thank you for helping us ensure a seamless stay!

Additional Services:
• Pool and hot tub heating are available upon request and are not included in the booking price. The fee is $45/night per service or $79/night for both, with a 2-night minimum. At least 24 hours’ notice is required if you would like to add this service.
• Planning a BBQ? A propane tank is available for a one-time $69 charge. Please let us know at least 24 hours in advance so we can have everything ready for you to enjoy the grill.
• Rent a Pack 'n play for $39 (one-time fee)
• Rent a highchair for $29 (one-time fee)
• 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.

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.

full description, the area, host notes

Managed by Upstay

Upstay
4.6★

22,541 reviews

Upstay is a vacation rental management company offering hand-picked, uniquely designed properties across multiple destinations including Orlando, Austin, Costa Rica, Canada, and Colorado. They provide curated accommodations ranging from family retreats to luxury villas, emphasizing comfort, style, and personalized travel experiences.

Browse all 515 properties
upstay.com

Guest Reviews

4.2★ · 32 reviews
All reviews →
★★★★★

“My Family And I Had A Great Stay. Host Was Great, Beautiful House, Spacious And Clean!”

Guest · Oct 2026

★★★★★

“Loved my stay the host didn’t take long to respond also house was beautiful and very peaceful”

Guest · Oct 2026

★★★★★

“The place was in a good location and the hosts were very responsive. Would book this place again.”

Guest · Nov 2024

Good for

Lake daysGroupsHot tub nights

Rules & Policies

Location

Kissimmee, Florida

Get directions →

Choose your stay

Select dates to see availability

2 guests
Your stay