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

Family-friendly holiday home with water park and fitness centre

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A heated pool - Sunny Winter Escape Near Disney | Private Pool | Comfortable Family Home (Kissimmee)
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5 bedrooms, iron/ironing board, travel cot, free WiFi - Sunny Winter Escape Near Disney | Private Pool | Comfortable Family Home (Kissimmee)
Gift shop - Sunny Winter Escape Near Disney | Private Pool | Comfortable Family Home (Kissimmee)
Experience the ultimate retreat at this luxurious 5-bedroom villa in Windsor Hills Resort, where you can unwind by the private screened-in pool and spa or explore themed bedrooms for unique experiences. With a dog-friendly accommodation and pet supplies provided, bring your furry friend along.

Reviews

10 out of 10
Exceptional

Entire home

5 bedrooms5 bathroomsSleeps 12

Popular amenities

  • Parking available
  • Pet-friendly
  • Dryer
  • Washer
  • Gym
  • Air conditioning

Add dates for prices

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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.

Property amenities

Pool/Spa

  • Communal pool
  • Heated pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Electric car charging station on site
  • Car recommended
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Spices
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 5 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Games
  • Smart TV with cable/satellite channels

Outdoor areas

  • Garden
  • Patio

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Office

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 2 pets total

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board
  • Phone

Location highlights

  • Near a hospital
  • Near an outlet shopping centre

Things to do

  • Arcade/game room
  • Billiards/pool table
  • Foosball table
  • Gym
  • Heated pool
  • Table tennis
  • Tennis
  • Water park
  • Basketball nearby
  • Theme park nearby

Safety features

  • Carbon monoxide detector not reported (host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Deadbolt lock

General

  • Electric car charging station
  • Garden

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets are allowed
Service animals are welcome, and are exempt from fees
Welcoming dogs only
2 total pets
Note from host: Dogs only

Children and extra beds

Children are welcome

Events

No events allowed

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

We should mention

A car is recommended for transport to and from this property

Property is also known as

orp5b63b4dx

About the area

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 Sunny Winter Escape Near Disney | Private Pool | Comfortable Family Home have a pool?

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

Is Sunny Winter Escape Near Disney | Private Pool | Comfortable Family Home pet-friendly?

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

How much is parking at Sunny Winter Escape Near Disney | Private Pool | Comfortable Family Home?

On-site parking is available at the property.

What time is check-in at Sunny Winter Escape Near Disney | Private Pool | Comfortable Family Home?

Check-in begins at 4:00 PM.

What time is check-out at Sunny Winter Escape Near Disney | Private Pool | Comfortable Family Home?

Checkout is at 10:00 AM.

Where is Sunny Winter Escape Near Disney | Private Pool | Comfortable Family Home 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).

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Reviews

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

10

Exceptional

10

Cleanliness

10

Location
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

Reviews

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

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

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

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