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Olaf's Endless Summer at Windsor Hills

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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 table and chairs, a swimming pool, and a view of the backyard.
Coffee/tea maker, fridge, microwave, oven
A hot tub with a curved edge, surrounded by a brick patio.

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms4 bathroomsSleeps 132000 sq ft

Popular amenities

  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

View in a map
Kissimmee, FL
  • Place, Bonanza Golf & Gifts
    ‪2 min drive‬
  • Place, Disney's Animal Kingdom® Theme Park
    ‪9 min drive‬
  • Place, Disney Springs™
    ‪12 min drive‬
  • Airport, Orlando, FL (MCO-Orlando Intl.)
    ‪31 min drive‬

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About the neighborhood

Kissimmee

Located in Windsor Hills, this villa is within a few miles (5 km) of sights such as Walt Disney World® Resort and Island H2O Live!. The villa includes a kitchen, a dining area, and a refrigerator.
View more Villas in OrlandoOpens in a new window

What's nearby

  • Bonanza Golf & Gifts - 2 min drive - 1.5 miles
  • Disney's Animal Kingdom® Theme Park - 9 min drive - 3.4 miles
  • ESPN Wide World of Sports Complex - 9 min drive - 4.2 miles
  • Disney Springs™ - 12 min drive - 9.3 miles
  • Magic Kingdom® Park - 13 min drive - 9.7 miles

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.

Olaf's Endless Summer at Windsor Hills

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, and make 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!
The villa is air-conditioned and features a kitchen and 4 bathrooms, and there's space to spread out with 4 bedrooms and a dining area. Guests can enjoy a Smart TV and stay connected with free WiFi. Other standard amenities include a washing machine, a coffee maker, and an ironing board.

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  • Kitchen
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Property amenities

Pool/Spa

  • Heated pool
  • Hot tub

Internet

  • Available in the villa: Free WiFi

Parking and transportation

  • Wheelchair-accessible parking available

Kitchen

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

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 4 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Shower

Living spaces

  • Separate dining area

Entertainment

  • Smart TV with cable/satellite channels

Outdoor areas

  • Barbecue grill
  • Porch/lanai

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.
  • 1"on-site accessible parking spaces 1", on-site accessible parking spaces
  • No elevator (single-level property)
  • Wheelchair-accessible parking
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Things to do

  • Arcade/game room
  • Gym
  • Heated pool

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

  • 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 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 complete the following before checking out:

Load and start the dishwasher

Strip any used beds and gather used towels

Remove personal items, remove leftover food and drinks, and take out the trash

Turn off the lights and lock the doors

Please refer to your check-in information.

Failure to complete these may result in a negative review from the host.

Pets

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 25

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a private host, not a professional engaged in trade or business.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.

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

Frequently asked questions

What can I see near this villa?

This villa is situated in Windsor Hills, close to Disney's Animal Kingdom® Theme Park, ESPN Wide World of Sports Complex, and Disney's Hollywood Studios®. You'll also find Walt Disney World® Resort and Mystic Dunes Golf Club within a short drive.

Is parking available on site at Welcome to Olaf's Endless Summer! Last-minute August cancellation Aug 14-21st.?

Yes, there is wheelchair-accessible parking available.

Is this villa next to a casino?

No, this villa is not connected to a casino.

Will I find an indoor pool at this villa?

No, this villa doesn't have an indoor pool; however, there is a hot tub.

What do couples enjoy most about Welcome to Olaf's Endless Summer! Last-minute August cancellation Aug 14-21st.?

Couples staying at this villa will appreciate amenities like a kitchen and a smart TV as well as a hot tub.

Does Welcome to Olaf's Endless Summer! Last-minute August cancellation Aug 14-21st. have a hot tub?

No, but guests can enjoy a heated pool at this villa.

Does this villa include breakfast service?

No, this villa doesn't offer breakfast.

Will this villa allow pets to stay for free?

No, pets aren't allowed at this villa.

Does Welcome to Olaf's Endless Summer! Last-minute August cancellation Aug 14-21st. have connecting rooms available?

No, there aren't connecting guestrooms at this villa.

How far is the airport from this villa?

The closest major airport to this villa is Kissimmee, FL (ISM-Kissimmee Gateway), which is 12.4 mi away (21 minutes by car). Another top airport is Orlando Intl. Airport (MCO), which is located 25.7 mi away (31-minute drive).

Are there rooms with balconies that I can book at Welcome to Olaf's Endless Summer! Last-minute August cancellation Aug 14-21st.?

Yes, every villa at Welcome to Olaf's Endless Summer! Last-minute August cancellation Aug 14-21st. comes with a porch/lanai.

Olaf's Endless Summer at Windsor Hills Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 21 out of 24 reviews
Rating 8 - Good. 2 out of 24 reviews
Rating 6 - Okay. 1 out of 24 reviews
Rating 4 - Poor. 0 out of 24 reviews
Rating 2 - Terrible. 0 out of 24 reviews

9.4/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Sharon K.

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

Erin L.

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

8/10 Good

Toni S.

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

Vanessa M.

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

Chris B.

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

Matthew M.

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

Burr W.

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

Jignesh P.

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

10/10 Excellent

Karen M.

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

Kendra P.

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

Erin L.

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

Destin C.

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

Madeline S.

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

Miriam M.

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

Ashlee C.

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

Karen D.

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

Jorge C.

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

10/10 Excellent

erik d.

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