Themed Disney Vacation Home • Private Pool • Minutes from Parks • Windsor Hills

Kissimmee, Florida
$299 avg/night
Minimum Stay 3 Nights
Bed 4

Bed

Bath 4

Bath

Home Villa

Property Type

Sleep 13

Max Sleeps

Night 3 nights

Min Stay

Welcome to Olaf’s Endless Summer – Your Family’s Magical Disney Retreat

Escape to a place where Disney dreams meet everyday comfort. Located just 2 miles from Walt Disney World, our professionally designed 4-bedroom, 4-bathroom villa in Windsor Hills Resort is the perfect in home base for your next adventure. Whether it’s your first visit or your fifteenth, Olaf’s Endless Summer offers the space, charm, and convenience families need to relax, recharge, andmake unforgettable memories.

Why Families Love Our Home:

Rare single-story layout—no stairs, no elevators, just walk-in ease

4 bedrooms / 4 bathrooms—everyone gets their own space and privacy

Private heated pool—perfect for nighttime swims under the stars

Themed bedrooms:

Star Wars™ Galaxy Room with custom triple-decker bunk bed—sleeps several kids

Princess Suite with pull-out trundle—perfect for siblings or cousins

Moana-Inspired Room with a king-size bed and private ensuite—a tropical escape for grown-ups

Frozen Room with a king-size bed and private ensuite—cool, cozy, and ideal for grandparents or parents

Games room with pool table, Xbox and more

Family-Ready Extras (Included!):
Pool heat included
Highchairs, strollers, playpens, wagons

Toy room stocked with fun

BBQ grill on the honor system

Smart TVs, fast Wi-fi.

We’re Not Just Hosts—We’re Here for You: We’re proud to be Premier Hosts with hundreds of 5-star reviews from happy families. Due to a glitch in the system (possibly caused by a rogue droid or a Jedi mind trick), they’re a bit tricky to find—but trust us, they’re there, and they speak volumes. We treat every guest like family and love being part of your vacation story.

Yes, we have a great management team, but we’re also just a phone call away. Whether you forgot to register someone at the gate, need a last-minute change, or want Brett’s “Dad’s First Day Check-In List,” we’re here to help.

Windsor Hills Resort Perks:

Heated lagoon pool, splash pad, and water park

Clubhouse with movie theater, arcade, and fitness center

Sports courts, playgrounds, walking trails

Daily activities like crafts and DJ-led pool parties (our daughter is undefeated in the hula hoop contest—15 wins and counting!)

Let the magic begin. Olaf’s Endless Summer is more than a rental—it’s a place where memories are made. Book today and let your family’s magical adventure begin!

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2000 Sq Ft (186 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Wheelchair-accessible Parking Available
  • INTERNET

    Free WiFi, With Speed Of 500+ Mbps (good For 6+ People Or 10+ Devices)
  • OUTDOORS

    Barbecue Grill Porch Or Lanai
  • POOL/SPA

    Heated Pool Hot Tub
  • BATHROOMS

    4 Bathrooms Bathtub Or Shower Hair Dryer
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Fitness Center
  • ENTERTAINMENT

    Arcade/game Room Smart TV With Cable/satellite Service
  • LIVING SPACES

    Dining Room Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Highchair
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    1 On-site Accessible Parking Spaces If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevator (single Level Property) Smoke-free Property Wheelchair-accessible Parking

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 13

Map Map

School District Availability

Review Review

  • Madeline S.

    Submitted Feb 2, 2026

    Stayed Jan 21, 2026

    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

  • Erin L.

    Submitted Jan 5, 2026

    Stayed Oct 21, 2025

    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!

  • Karen M.

    Submitted Dec 28, 2025

    Stayed Dec 22, 2025

    Great house. Loved all the amenities

  • Vanessa M.

    Submitted Oct 8, 2025

    Stayed Sep 24, 2025

    The property was fantastic and the hosts were amazing. We loved staying here.

  • Karen D.

    Submitted Aug 23, 2025

    Stayed Aug 12, 2025

    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

  • Ashlee C.

    Submitted Aug 4, 2025

    Stayed Jul 31, 2025

    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

  • Miriam M.

    Submitted Jul 23, 2025

    Stayed Jul 19, 2025

    Every kitchen utensil you can think of! Comfortable and clean.

  • Destin C.

    Submitted Jul 16, 2025

    Stayed Jun 26, 2025

    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!

  • Burr W.

    Submitted Apr 20, 2025

    Stayed Apr 13, 2025

    Wonderful location and property with a large number of bedrooms and bathrooms. Close proximity to Disney.

  • Jorge C.

    Submitted Mar 30, 2025

    Stayed Mar 27, 2025

    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.

  • Jackie T.

    Submitted Mar 3, 2025

    Stayed Feb 17, 2025

    Great location, close to Disney parks and many restaurants and stores. Home was clean and provided a good time for all.

  • Maureen A.

    Submitted Jan 11, 2025

    Stayed Dec 9, 2024

    We love this home. We were traveling with our kids and our parents. So, 4 adults and 2 kids. The kids love the pool, playroom and there’s bedrooms. House is super clean and well located. We will stay here again when visiting Florida.

  • Michael F.

    Submitted Jan 1, 2025

    Stayed Dec 27, 2024

    Property is very clean, layout is excellent and spacious for the capacity of the group, and the pool and play areas are exactly as advertised, providing more than ample room for all to comfortably hang. The kids really enjoyed the pool which was plenty warm for December. The main pool at the complex was also very warm and pleasant given the season; and again, the pictures matched the physical appearance of the main pool which was very much enjoyed by all.

  • Katie S.

    Submitted Nov 22, 2024

    Stayed Nov 15, 2024

    The house was nice, clean, it was easy to communicate with the owners and the community is awesome, it’s actually our 2nd time staying in this gated community. That being said it is basic - do not expect anything to be left behind from other renters, the house is VERY cleaned out and missing things that I didn’t need to bring/purchase for other vacation rentals such as general cleaning products. There were remotes missing batteries, the grill definitely could use some general maintenance, we weren’t able to use it because it needed a deep cleaning and the propane valve was stuck. The pillows were also pretty rough. We just did not get that home away from home feeling with this house. That being said I would recommend it to a busy family not planning on spending a ton of time in the home which is thankfully what we were. Overall a very nice home.

  • Shana S.

    Submitted Aug 3, 2024

    Stayed Jul 25, 2024

    The place was exactly as described. We very much enjoyed our stay. The host was attentive and responded quickly. The house had everything we needed to vacation like we were at home. Thank you.

  • Brandon K.

    Submitted Jul 9, 2024

    Stayed Jun 11, 2024

    Great house in nice neighborhood very close to the Disney parks. Couldn't ask for more

  • Nathaniel C.

    Submitted Jun 22, 2024

    Stayed Jun 15, 2024

    Enjoyed the property so much we made a return visit.

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Total

Includes taxes and fees
$299+
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