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Windsor Hills 4BR | Heated Pool | Near Disney

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A resort with a large swimming pool, a water park, and multiple hotel buildings.
Property video
An outdoor patio with a glass enclosure, a pool, and outdoor furniture.
Full kitchen for easy family meals at home
A two-story house with a front driveway, a garage, and a well-maintained lawn.

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms4 bathroomsSleeps 13186 sq m

Popular amenities

  • Spa pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View map
Kissimmee, FL
  • Place, Bonanza Golf & Gifts
    ‪2 min drive‬
  • Place, Universal Orlando Resort
    ‪20 min drive‬
  • Place, Universal Studios Florida
    ‪24 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪31 min drive‬

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About the area

Kissimmee

A family-friendly stay in Kissimmee awaits you at this villa. You'll be 4.9 km (3 mi) from Walt Disney World® Resort and 3.4 km (2.1 mi) from Island H2O Live!. .Villa features a private pool, a washing machine and free WiFi. In-room dining is easy with a kitchen that comes equipped with a fridge, a microwave and a stovetop. 4 bathrooms, a balcony and a living room are also available. .Enjoy the water park, outdoor swimming pool, gym and Hot tub. Other amenities include laundry facilities, a garden and barbecues.
View more Villas in OrlandoOpens in a new window

What's nearby

  • Bonanza Golf & Gifts - 2 min drive - 2.4 km
  • Disney Springs™ - 12 min drive - 15.7 km
  • Magic Kingdom® Park - 13 min drive - 15.7 km
  • Universal Orlando Resort - 20 min drive - 28.8 km
  • Universal Studios Florida - 24 min drive - 31.8 km

Getting around

  • Kissimmee Station - 25 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 21 min drive

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Starbucks - ‬2 min drive
  • ‪El Cafetal Bakery & Restaurant - ‬2 min drive
  • ‪Del Taco - ‬3 min drive
  • ‪IHOP - ‬3 min drive

About this property

Entire place

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

Windsor Hills 4BR | Heated Pool | Near Disney

Come home from the parks to your own heated pool, themed bedrooms, and space for the whole family to unwind. Olaf’s Endless Summer is a single-story, 4-bedroom, 4-bathroom villa in Windsor Hills Resort, approximately 2 miles from Walt Disney World. Pool heat is included, and the home sleeps up to 13 guests.



YOUR FAMILY’S HOME BASE

• Private screened pool and lanai for swims, outdoor meals, and relaxed evenings

• Pool heat included in your stay

• Four bedrooms and four bathrooms, including two king bedrooms with private ensuites

• Single-story living, with no interior stairs between living areas and bedrooms

• Games room with a pool table and Xbox, plus a toy room for younger guests

• Full kitchen, dining space, washer and dryer, Smart TVs, and Wi-Fi



BEDROOMS WITH A LITTLE MAGIC

• Moana-inspired room: king bed and private ensuite

• Frozen-inspired room: king bed and private ensuite

• Star Wars-inspired room: custom bunk setup with a queen, double, and single bed

• Princess room: double bed and two single beds, including a pull-out trundle



The themed rooms give children something to look forward to, while the two king bedrooms make sharing the home with grandparents or another family easier. Please review the room photos and bed arrangements to make sure they suit your group.



PACK LESS, ENJOY MORE

Highchairs, strollers, playpens, and wagons are available, along with toys for younger guests. A BBQ grill is available on an honor-system basis.



WINDSOR HILLS RESORT

Enjoy the resort’s lagoon pool, splash pad and water park, clubhouse, movie theater, arcade, fitness center, sports courts, and playgrounds. Resort facilities and activities are subject to operating hours and availability.



CLOSE TO THE PARKS, WITH ROOM TO RECHARGE

Spend the day exploring Walt Disney World, then return for a pool break, a family meal, or a friendly game of pool. The approximately 2-mile distance is to Walt Disney World; driving times vary by park and traffic.



HOSTED BY JANETTE AND BRETT

We’re Premier Hosts who love helping families enjoy their Orlando vacation. Our management team supports your stay, and we’re also just a phone call away when you need help.



Choose your dates and make Olaf’s Endless Summer your family’s Windsor Hills home base.

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  • Pool
  • Kitchen
  • Washing machine
  • Dryer
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Property amenities

Beach

  • Beach loungers

Pool/Spa

  • Heated pool
  • Hot tub
  • Outdoor pool
  • Private pool

Internet

  • Available in the villa: Free WiFi

Parking and transport

  • Car required
  • Wheelchair-accessible parking available

Kitchen

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

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 4 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Living room

Entertainment

  • TV with cable/satellite channels
  • Video games

Outdoor areas

  • Balcony
  • Barbecue grill
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Accessible parking space
  • No lift (single-level property)
  • Wheelchair-accessible parking
  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Things to do

  • Gym
  • Heated pool
  • Water park
  • Basketball nearby
  • Golfing nearby
  • Swimming nearby
  • Theme park nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden
  • Property located in a resort
  • Unit size: 2,000 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

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

Check-out instructions

The host requires you to complete the following before checking out:
Load and start the dishwasher
Gather used towels
Take out the rubbish
Turn off the lights and lock the doors
Our cleaners arrive at 10am sharp, please respect the check out time.
Failure to complete these may result in a negative review from the host.

Rules

The thermostat stays at 72 degrees - no tampering. There are no more than 3 cars allowed on the property.
Pool heat included; target 85F. Pool/spa temperatures depend on weather and are not guaranteed. Heating may be limited in cold conditions.
Guests responsible for cleaning the BBQ after and filling the propane tank. If a guest is not registered by owner 24 hrs in advance, no admission.

Pets

  • No pets allowed

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 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
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children. If you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher and a smoke detector in all accommodation.

Property is also known as

Close to Disney Themed Kids Rooms Gated Resort Community
Sept Oct Book FOR $119/night!!! This Is An Incredible Deal!
Family Oriented, Disney Styled Vacation Pool Home! Kissimmee
orp5b77ef8x

Frequently asked questions

Are there any beaches close to Windsor Hills 4BR | Heated Pool | Near Disney?

The closest beach to Windsor Hills 4BR | Heated Pool | Near Disney is Hideaway Bay (8.3 km).

Does Windsor Hills 4BR | Heated Pool | Near Disney have a pool?

Windsor Hills 4BR | Heated Pool | Near Disney has a heated pool and a pool.

Does Windsor Hills 4BR | Heated Pool | Near Disney have a waterslide?

No, but it has a waterpark and lazy river.

What luxury perks are available at Windsor Hills 4BR | Heated Pool | Near Disney?

This property features a heated pool, as well as a private pool and a living room.

What makes Windsor Hills 4BR | Heated Pool | Near Disney a romantic place to stay?

1 hot tub, private pools, and private balconies all help set the scene for a sizzling getaway at Windsor Hills 4BR | Heated Pool | Near Disney.

Is Windsor Hills 4BR | Heated Pool | Near Disney family-friendly?

You bet! With amenities such as a water park and laundry facilities, as well as baby monitors and highchairs, it's no surprise that Windsor Hills 4BR | Heated Pool | Near Disney is a winner with our family travellers.

Is there a private hot tub at Windsor Hills 4BR | Heated Pool | Near Disney?

Yep, there is a hot tub.

Is there a free airport shuttle available at Windsor Hills 4BR | Heated Pool | Near Disney?

No, Windsor Hills 4BR | Heated Pool | Near Disney does not offer an airport shuttle service.

What time are check-in & check-out at Windsor Hills 4BR | Heated Pool | Near Disney?

Check-in begins at 4:00 PM. Check-out time is 10:00 AM.

Are pets allowed at Windsor Hills 4BR | Heated Pool | Near Disney?

No, pets are not allowed.

Windsor Hills 4BR | Heated Pool | Near Disney Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 25 out of 29 reviews
Rating 8 - Good. 3 out of 29 reviews
Rating 6 - Okay. 1 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

9.6/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
It was a wonderful house and a perfect stay!
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was great with plenty of space and in a great location. Decorations were fun and the pool was very nice! Playroom was a nice bonus.
Stayed 7 nights in Jul 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home was perfect for our stay. We had plenty of room, everything we needed and the proximity to Disney World was great!
Stayed 7 nights in Apr 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great stay! Incredibly close to Disney!
Stayed 7 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house for our traveling party. Very clean and everything you could want is there.
Stayed 14 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
The property was fantastic and the hosts were amazing. We loved staying here.
Stayed 14 nights in Sep 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic house in a well located resort a short 10-15 minute drive from the entire WDW resort. House as described and was a lovely home away from home! Owner quick to respond to enquiries, would definitely stay again!
Stayed 10 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We enjoyed our stay immensely from start to finish.......house contained everything a family could need for an excellent relaxing stay and we would therefore recommend it to future clients who may be considering staying.The clubhouse with slides, pools, etc just down the road, a very short distance was extremely pleasant, as was the games room in the garage and for some, the large TV under the lanai by the pool.We couldn't fault anything on our visit but we would recommend a change of sun beds by the pool as the present ones are a mite uncomfortable with no padding or cushions.Thanks for the stay .....we would definitely recommend it to our friends and family
Stayed 9 nights in May 2026
Verified review

10/10 Excellent

Host was very attentive.
Stayed 4 nights in Feb 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay for Summit was amazing! The house was spotless, quiet, and had the best amenities for both kids and adults. The personal pool, kids’ playroom, and waterpark access made it feel like a vacation on top of competition weekend. The rooms were somehow even better in person than the pictures, and my kiddos absolutely loved every second of it. My daughter is already asking if we can book this same house again next year if we make it back to Summit! Highly recommend for families traveling for competitions or just wanting a fun, relaxing stay.
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great house. Loved all the amenities
Stayed 6 nights in Dec 2025
Verified review

10/10 Excellent

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

Great place to stay.

Wonderful location and property with a large number of bedrooms and bathrooms. Close proximity to Disney.
Stayed 4 nights in Apr 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We stayed in late Oct for a Disney trip and loved the condo! Our kids especially loved the playroom with all the fun toys, the themed rooms and the outside pool area! We really appreciated how well stocked the condo was - from the pool toys to the beach towels, and indoor toys (dress up clothes, video games), there was lots to keep everyone entertained and happy when we weren’t at the parks!
Stayed 5 nights in Oct 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was amazing! Host was great with communication! Pool heat and Bbq grill included in cost a big plus. Very nice quiet community with great location to Disney. So many extra touches did not go unnoticed- pool toys- kids toys- strollers
Stayed 7 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful place! It was well appointed with everything you could need! The owners were amazing. When an unlikely issue popped up, they were quick to reach out to us directly and make everything right as best they could. We would definitely stay here again!
Stayed 9 nights in Jun 2025
Verified review

10/10 Excellent

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

Great house

Every kitchen utensil you can think of! Comfortable and clean.
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
First off our host was simply amazing! My family and I absolutely loved our stay especially the pool! It was my daughter’s 12th birthday and this was a surprise trip. We will be coming back soon! #Olafsendlesssummer
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
From initial contact with the owner to check out this experience has been a joy. I can’t recommend this property or the owner enough. Spotlessly clean house with every available item that you would need. Gorgeous neighborhood. Safe and well maintained. Can’t wait to come backKids don’t want to go home
Stayed 11 nights in Aug 2025
Verified review

10/10 Excellent

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

Clean and great location

House was clean and as described. It was well stocked with utensils, cups, and cooking supplies. The pool and whirlpool were clean. The furniture was is great condition. Note you cannot adjust the thermostat as it is locked.
Stayed 3 nights in Mar 2025
Verified review

6/10 Okay

Liked: Communication, listing accuracy
Disliked: Check-in
The biggest area for improvement is the cleaning. While the surfaces appeared clean, it didn't seem like the home receives regular deep cleaning. The ceiling fans were so dusty that dust flew off when we turned them on, making them unusable. We also found a dead cockroach in one of the front bedrooms that should have been caught during cleaning. With frequent guest turnover, deeper cleaning should be a priority. The welcome packet also needs updating. It stated there was only a standard coffee maker, so we bought a small Keurig, only to find the coffee maker actually has a Keurig attachment built in. Having accurate information would have saved us the unnecessary purchase. Another suggestion is to provide more guidance for guests who are not traveling with a car. The welcome information seems to assume everyone will have their own vehicle. We arrived by Uber and planned to spend some time at the clubhouse before check-in, only to learn that the clubhouse does not assist with luggage storage or transportation. We had to keep our luggage with us until 4:00 p.m. and then arrange our own way to get it to the house, which is not within easy walking distance. The host did have the property managers assist us, which we appreciated, but knowing this information ahead of time would have allowed us to plan differently Overall we enjoyed our stay, but with improved deep cleaning and more up-to date, detailed guest information, this would be an even better experience.
Stayed 7 nights in Jul 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing home. Amazing host. Amazing trip. We have stayed at Windsor Hills homes, townhouses, and condos for every WDW our family has had since 2005 and this was one of our best experiences! :)
Stayed 8 nights in Jun 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, listing accuracy
Stayed 10 nights in Jun 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 3 nights in Aug 2024