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Sunny Winter Escape Near Disney | Private Pool | Comfortable Family Home

Family-friendly holiday home with water park and fitness centre

Photo gallery for Sunny Winter Escape Near Disney | Private Pool | Comfortable Family Home

Wild Sky's Poolside Magic
Open-Plan Living: Kitchen, Dining & Lounge
Frozen Fantasy: Princess-Worthy Retreat
Power-up paradise: Mario-themed gaming headquarters
Dining flows to living and pool

Reviews

10 out of 10, Loved by Guests
5 bedrooms5 bathroomsSleeps 12

Popular amenities

  • Parking available
  • Pet-friendly
  • Dryer
  • Washer
  • Outdoor space
  • Gym

Explore the area

View in a map
Kissimmee, FL
  • Place, Mystic Dunes Golf Club
    ‪18 min walk‬
  • Place, Bonanza Golf & Gifts
    ‪3 min drive‬
  • Place, Walt Disney World® Resort
    ‪6 min drive‬
  • Airport, Kissimmee, FL (ISM-Kissimmee Gateway)
    ‪24 min drive‬

Rooms & beds

5 bedrooms (sleeps 12)

Frozen

2 Single Beds

Mandalorian

2 Single Beds, 1 Double Bed and 1 Single Bunk Bed

Primary 1

1 King Bed

Primary 2

1 King Bed

Upstairs Suite

1 Queen Bed

5 bathrooms

Frozen

Bathtub or shower · Toilet

Mandalorian

Bathtub or shower · Toilet

Primary 1 Bathroom

Toilet · Shower only

Primary 2

Toilet · Shower only

Upstairs Suite

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Office
Outdoor play area
Garden
Dining area

About this property

Sunny Winter Escape Near Disney | Private Pool | Comfortable Family Home

Relax in a spacious 5BR/5BA villa just minutes from Disney, designed for comfort, space, and an easy Florida stay. Perfect for families and groups, this private home offers resort-style amenities without the crowds or hassle.

Welcome to Wild Sky Retreats at Windsor Hills Resort — a comfortable, family-friendly getaway close to the magic. Our thoughtfully designed villa blends space, fun, and functionality for stress-free vacations with family and friends.

Inside the Villa
• 5 bedrooms and 5 full bathrooms — ideal for multi-generational trips
• Two king suites with en-suite baths for privacy and comfort
• Mandalorian and Frozen themed bedrooms
• Bright, open living areas with a fully equipped kitchen and dining space
• Mario-themed game room
• Smart TVs and fast, reliable Wi-Fi
• Dog-friendly (see house rules for details)

Outdoor Living
• Screened lanai with outdoor dining and seating
• Private pool and spa (pool heat available seasonally)
• Child safety features for peace of mind

Windsor Hills Resort Amenities
• Lagoon-style pool
• Water slides
• Cabanas
• Fitness center
• Sports courts
• Playgrounds
• Movie theater
• On-site sundry shop

Location Highlights
• Approximately 2 miles from Walt Disney World
• Easy access to Universal Studios and SeaWorld
• Close to dining, shopping, and entertainment
From morning coffee by the pool to relaxed evenings under the lanai, every detail is designed to make your stay comfortable and memorable.

⚠️ Important: The Windsor Hills water park and slides will be closed for refurbishment Jan 5 – Feb 6, 2026. All other resort amenities, including the lagoon pool and cabanas, will remain open.

Add dates for prices

Amenities

Pool
Kitchen
Washing machine
Dryer
Pet-friendly
Free WiFi

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House Rules

Check in after 4:00 PM
Minimum age to rent: 21
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

Pets allowed: dogs (limit 2 total)
Dogs only
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Smoking

Smoking is not permitted

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
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

A car is recommended for transport to and from this property

About the area

Kissimmee

Located in Windsor Hills, a neighbourhood in Kissimmee, this holiday home is near theme parks. Old Town and Flamingo Crossings Town Center are worth checking out if shopping is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Disney's Hollywood Studios®. Travelling with kids? Make time for Epcot®, or head to an event or a match at ESPN Wide World of Sports Complex.
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Map
Kissimmee, FL

What's nearby

  • Mystic Dunes Golf Club - 18 min walk - 1.6 km
  • Bonanza Golf & Gifts - 3 min drive - 3.1 km
  • Walt Disney World® Resort - 6 min drive - 5.1 km
  • Disney's Animal Kingdom® Theme Park - 7 min drive - 4.8 km
  • Disney Springs™ - 11 min drive - 13.7 km

Getting around

  • Kissimmee Station - 35 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 30 min drive

Restaurants

  • ‪McDonald's - ‬4 min drive
  • ‪Starbucks - ‬3 min drive
  • ‪Del Taco - ‬4 min drive
  • ‪Sickies Garage Burgers & Brews - ‬4 min drive
  • ‪Drafts Sports Bar & Grill - ‬16 min walk

Frequently asked questions

Does December Deal! Private Heated Pool • Arcade • 5BR Near Disney have a pool?

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

Is December Deal! Private Heated Pool • Arcade • 5BR Near Disney pet-friendly?

Yes, this property allows dogs (limit 2 total).

How much is parking at December Deal! Private Heated Pool • Arcade • 5BR Near Disney?

On-site parking is available at the property.

What time is check-in at December Deal! Private Heated Pool • Arcade • 5BR Near Disney?

Check-in begins at 4:00 PM.

What time is check-out at December Deal! Private Heated Pool • Arcade • 5BR Near Disney?

Checkout is at 10:00 AM.

Where is December Deal! Private Heated Pool • Arcade • 5BR Near Disney located?

This family-friendly Kissimmee holiday home is located in Windsor Hills, within 3 mi (5 km) of Mystic Dunes Golf Club and Island H2O Live!. Walt Disney World® Resort and Old Town are also within 6 miles (10 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 11 out of 11 reviews
Rating 8 - Good. 0 out of 11 reviews
Rating 6 - Okay. 0 out of 11 reviews
Rating 4 - Poor. 0 out of 11 reviews
Rating 2 - Terrible. 0 out of 11 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Kimberly V.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The home was exactly how described. Very clean, also the little extras made it even better. The owner thought of everything. Every game in the game room worked, no glitches. Very close to Disney, Disney Springs. Very comfortable and roomy with high quality linens, towels, kitchen items, etc. My family will definitely stay in this unit again.
Stayed 6 nights in Sep 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Catherine A.

Great stay

This is a beautifully maintained villa which is furnished to a high standard. Kelly is extremely responsive and has thought of everything to ensure a comfortable stay! Personal preference for beds would be more doubles rather than bunk beds and twins but for families with young children this set up is great. My children are older so a personal choice. I would 100 per cent recommend to friends and family. Thanks for a great stay 😊

10/10 Excellent

Melissa C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Our Stay Was AMAZING!!! We Highly Recommend!!!!!

We had an absolutely wonderful stay at this vacation home! The property was spotless, beautifully decorated, and had everything I needed for a relaxing getaway. The location was perfect—peaceful, yet close to local attractions and restaurants. The hosts were incredibly responsive and made sure everything was just right. I would highly recommend this place to anyone looking for a comfortable and memorable stay. Can’t wait to come back!Thank you again, Kelly!MelissaNB, Canada
Stayed 7 nights in May 2025

10/10 Excellent

C&J R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Vacation Home

Property was great, furnished beautifully. Lots of extras included like cleaning and laundry supplies, coffee pods. Conveniently located close to Disney, I4 and lots of activities along HWY 192/Irlo Bronson
Stayed 7 nights in Feb 2025

10/10 Excellent

Alan M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

2025 Vacation

My family and I (three generations) had a wonderful stay at Wild Sky Retreat in April 2025. We stayed for 15 nights in the run up to the Easter weekend.The property is beautifully equipped and presented. Windsor Hills is a lovely development with high standards and perfectly located for accessing the main parks and a short hop back to relax around the pool.There are plenty of good quality dining and retail opportunities within easy reach.Kelly was a very helpful and professional host.All in all it provided an ideal base for a lovely holiday.Highly recommended.
Stayed 15 nights in Apr 2025
This review comes from a trusted partner site and has not been verified.

10/10 Excellent

Dawn B.

Cozy

It felt like a home away from home, very cozy and organized. Instructions were very clear, no unnecessary hassle and when I reached out with a question I received a response almost immediately which was a major plus for me. Overall I would definitely book this rental again.

10/10 Excellent

Stacy M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing house

This property has it all! There is plenty of room for everyone with all the bedrooms. My teens and I enjoyed the game room. This property provided things that others do not such as toilet paper, paper towel, laundry detergent and shampoo. There was even an air fryer! The house was clean and the instructions were very straight forward. Management answered questions with no delay. We enjoyed the private pool as well as the property main pool. Super close to all things Disney along with ton of shops and restaurants. We will definitely be staying again.
Stayed 7 nights in Mar 2025

10/10 Excellent

Hannah W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Stay for Disney weekend

Amazing home! Perfectly clean, newly decorated, most well-stocked rental I’ve ever been in. Every little detail was covered… from kitchen items, to bathroom toiletries, to dog treats and bags. The neighborhood is full of rentals, so they’re set up for a smooth process from the moment you get to the security gate. Enjoyed my time at the home even more than time at the Disney parks. Kids couldn’t wait to get back to the pool and game room each day. Cannot say enough good things. Thank you, Kelly!!
Stayed 4 nights in Feb 2025

10/10 Excellent

Madhurii B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Immaculate, comfortable, well stocked home in great location

Our family of 4 just spent 9 days at this cozy and comfortable home while we were in town for a Disney vacation with our two boys ages 6 and 12. They loved the game room and the pool as well as the themed star wars bedroom. We have rented several houses near Disney over the years and have never encountered such a well stocked home in this area. It was so nice not to have to worry about purchasing laundry detergent or coffee filters, olive oil, salt/ pepper or other household basics and instead we were able to just relax and enjoy our vacation. Kelly was very responsive and friendly, check in couldn't have been easier and the location was great-a super easy 15 minute drive to any of the parks with restaurants and grocery options just 5 minutes away. We will be back!
Stayed 9 nights in Apr 2025

10/10 Excellent

Courtney B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Best VRBO experience I have ever had

This was by far the best vrbo experience my family and friends have ever had. Kelly responded to all of my questions almost immediately. She was incredibly accommodating. The house came completely furnished, And by that I mean, we had plenty of garbage bags, paper towels, laundry pods, extra towels, toiletries and dish soap. It was spotless, the beds were comfortable, and there were even dog treats waiting for us. 10/10 would recommend these wonderfully thoughtful hosts!
Stayed 7 nights in Nov 2024

10/10 Excellent

Nancy F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wild Sky Retreats is wonderful & enjoyable to all!

My family & I, nine in total & 2 small dogs just came back from a fabulous vacation (10 days) at Kelly’s Wild Sky Retreats! It has so much room for everyone with 5 bedrooms & 5 bathrooms…3 of the bedrooms downstairs! She has a beautiful backyard pool and a game room which was a hit with everyone, esp. my grandchildren! Kelly’s attention to detail is noticed throughout her beautiful home! Each bedroom has an attached bathroom. Definitely accommodating to many families or family members. Kitchen utensils, bowls and children’s dishes are all good quality. The pool is great and most of all the safety features. There were two features that helped with parents watchful eyes to keep the little ones safe. Kelly has a pool safety gate. She also has a pool alarm that will go off if either slider is opened! There is a button on the wall that is to be pushed to stop the alarm. I’ve never seen this type of alarm, but it definitely helped in addition to the parents in keeping the little ones safe!!The neighborhood also offered the community pool and water park in addition to a couple parks, arcade & restaurant! It’s a neighborhood that has it all! We loved our stay and will definitely plan to come back! Just know if you are trying to decide between different VRBO properties, that you can’t go wrong with selecting Wild Sky Retreats!
Stayed 11 nights in Jun 2025

About the host

Hosted by Kelly

Host profile image
I'm Kelly, and I'm thrilled to welcome you to our family-run villa. Along with my wonderful mom and college-aged kids, we've created a perfect home-away-from-home for your Orlando adventure! Raised in Florida, and lifelong Disney and Universal enthusiast, I've lived and traveled all over the globe, picking up some great ideas to make your vacation truly special! We can't wait to help you create amazing memories here in the Sunshine State!

Why they chose this property

✨ Why Choose This Villa Over the Rest
🏰 Just a Few Miles from Disney
You’ll be at the gates in minutes — no long commutes, no wasted park time. Universal Studios, SeaWorld, and top Orlando attractions are also within easy reach, plus beaches, shopping, and dining for perfect non-park days.

🌟 Stand-Out Features You Won’t Find in Every Windsor Hills Home

5 true bedrooms with 5 full bathrooms — giving every guest their own space
Two king master suites with en-suites for ultimate privacy
Designer-curated décor — fresh, modern, and inviting
Fully stocked gourmet kitchen with quality cookware, not just the basics
Upgraded beds & linens for hotel-quality sleep
Smart TVs + white noise machines in king & queen rooms for comfort
🎭 Immersive Fun for All Ages
Mandalorian and Frozen themed bedrooms to keep the magic alive after the parks
Mario-themed game room with air hockey, foosball & console gaming
Pet-friendly with supplies so your furry family members are welcome too
🏊 Private Outdoor Oasis
Screened-in pool & spa with child safety features
Plenty of comfortable seating and a shaded lanai for dining or relaxing
🌴 Full Resort Access
💡 What Sets Us Apart
This isn’t just a rental — it’s a carefully maintained, thoughtfully outfitted home hosted by a small, hands-on team. We focus on the details that make your trip stress-free: responsive communication, a spotless home, and extras that turn a good vacation into an unforgettable one. Our guests consistently share how we go the extra mile to make their stay special.

What makes this property unique

✨ Unique Benefits of Staying at Wild Sky Retreat

So much in our villa is brand new! The lower level features three bedrooms, including two master suites, while the upper level has two more bedrooms — each with its own full bathroom for ultimate comfort and convenience. No morning lines here!

We provide hospitality-quality linens and towels for every guest, plus beach towels for pool days. Each bathroom includes a hair dryer and complimentary bath amenities to make getting ready for the parks easy.

🏊 Private Pool & Spa (pool heat available seasonally)
Step outside to your screened-in lanai with private pool and spa, surrounded by new overhead fans, plenty of patio seating, and a child safety fence. The sliding door to the pool has a child safety alarm for extra peace of mind.

👶 Family & Baby-Friendly
Traveling with little ones? We’ve got you covered with a stroller, Pack ’n Play (with sheets), high chair, booster seat, and kids’ plates/cups.

🧺 Home Comforts
Enjoy the convenience of a full-size washer & dryer, iron and ironing board, and complimentary laundry supplies.

📺 Entertainment & Connectivity
Complimentary secure high-speed Wi-Fi keeps you connected, and all TVs are Smart TVs so you can stream your favorites. A landline phone is also available.

🔐 Easy, Secure Entry
Our keyless entry with a high-security number lock means no worrying about keys — just arrive and start relaxing.

We respond promptly to all inquiries and are always happy to share more about Wild Sky Retreats or help with trip planning to make your stay unforgettable.

Languages:

English

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