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Last-Minute Deal! 4BR/4B Disney Villa - Pool, Themed StarWars & Princess -2mi DW

Family-friendly villa with a fitness center and a hot tub

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A heated pool
Fridge, microwave, oven, stovetop
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Fridge, microwave, oven, stovetop
Exterior
In the upscale Resort of Windsor Hills, Olaf's Endless Summer offers a family-friendly retreat less than 2.5 miles from Disney World. Relax in the screened-in pool/spa and lanai with outdoor Smart TV, or let kids unwind in the Under The Sea games room with a pool table and fooze ball.

Reviews

10 out of 10
Exceptional

Entire home

4 bedrooms4 bathroomsSleeps 10186 sq m

Popular amenities

  • Dryer
  • Washer
  • 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.

Last-Minute Deal! 4BR/4B Disney Villa - Pool, Themed StarWars & Princess -2mi DW

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 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 air hockey, foosball, and more

Family-Ready Extras (Included!):

Highchairs, strollers, playpens, wagons

Toy room stocked with fun

BBQ grill on the honor system

Smart TVs, fast Wi-Fi, and cozy living spaces

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: We’ve hosted birthdays, reunions, first-time Disney trips, and more. 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!

We also have a story that our guests shared with us that we would like to share with you!

The big vacation had finally arrived. We’d booked Olaf’s Endless Summer through VRBO several months ago, and the countdown had been on ever since. The hosts had provided everything we needed—directions, gate codes, check-in details—but what really stood out was Brett’s personal touch. I’d asked if they had any tips for the first day, and sure enough, Brett sent over a list. Not just any list—this was a “Dad’s First Day Check-In Guide,” complete with snack suggestions, pool priorities, and a reminder to charge your phone before the castle pics started piling up. We knew we were in good hands.

Grandma and Grandpa settled into the Moana-inspired king suite, grateful for the walk-in access and private ensuite. As Grandpa set down his suitcase, he chuckled, “Well, that beat the 5,000 steps I got checking into the other resort!” Everyone laughed—this trip was already off to a smoother start.

The next morning, while the adults sipped coffee poolside and admired the rising sun, the kids burst out of the toy room, declaring, “We’re hungry!” Brett’s tip from the welcome guide paid off instantly. Dad stood up and shouted, “There’s cheese pizza in the fridge!” The kids erupted in cheers—“YEAH!”—and raced inside like it was rope drop at Magic Kingdom.

After breakfast, the whole family went for a walk through Windsor Hills. Just a few minutes from the villa, they stumbled upon the massive castle playground—turrets, slides, bridges, and climbing walls that looked straight out of a fairytale. The kids were instantly enchanted, playing for over an hour while the adults relaxed nearby.

Dad watched them from a shaded bench and chuckled, “This beats the wooden tree fort I had growing up. I still remember the splinters!” Grandpa nodded knowingly, rubbing his hand like he could still feel one. The playground echoed with laughter, and for a moment, time slowed down—just long enough for everyone to feel like a kid again.

After lunch, they grabbed the pool towels—conveniently supplied in the villa—and headed to the Windsor Hills clubhouse. The kids raced to the waterslides, squealing with delight as they zipped down again and again. Meanwhile, the adults enjoyed drinks and snacks from the onsite café, soaking in the sunshine and the rare quiet. At the craft station, the kids got matching glitter tattoos—and even Mom and Grandma joined in, proudly showing off their sparkly designs. It was one of those spontaneous moments that turned into a favorite memory. Eventually, they headed back to the house to unwind.

That evening, Dad fired up the Weber BBQ on the patio. Steaks sizzled for the grown-ups while hot dogs roasted for the kids. The smell of dinner mixed with the warm Florida breeze, and everyone gathered around the outdoor table to eat, laugh, and share stories from the day. After supper, it was time for some cards and swimming. The kids picked a movie—Bluey!—and floated in the pool on intertubes, giggling and splashing as the screen glowed from inside. When Bluey ended, they begged for Moana… again. No one minded.

Suddenly, loud bangs echoed in the distance. They looked up and saw bursts of color lighting up the sky—Disney fireworks! From the pool deck, they caught a glimpse of the magic, a perfect surprise to end the night. Realizing it was late, they wrapped up the towels, turned off the lights, and called it a night.

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

  • Living room
  • 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 accessible parking space
  • 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

Similar properties

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

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

Pets not 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
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

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

About the neighborhood

Windsor Hills, a neighborhood in Kissimmee, is home to this villa. 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®. Traveling with kids? Don't miss Disney's Blizzard Beach Water Park and Disney's Animal Kingdom® Theme Park.
Map
FL, Kissimmee

What's nearby

  • Mystic Dunes Golf Club - 3 min drive - 2.0 km
  • Disney's Animal Kingdom® Theme Park - 6 min drive - 4.1 km
  • Disney's Blizzard Beach Water Park - 7 min drive - 6.5 km
  • ESPN Wide World of Sports Complex - 7 min drive - 6.4 km
  • Disney's Hollywood Studios® - 8 min drive - 7.8 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
  • ‪Del Taco - ‬3 min drive
  • ‪Drafts Sports Bar & Grill - ‬13 min walk
  • ‪Sickies Garage Burgers & Brews - ‬3 min drive

Frequently asked questions

Does Last-Minute Deal! 4BR/4B Disney Villa - Pool, Themed StarWars & Princess -2mi DW have a pool?

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

Is Last-Minute Deal! 4BR/4B Disney Villa - Pool, Themed StarWars & Princess -2mi DW pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Last-Minute Deal! 4BR/4B Disney Villa - Pool, Themed StarWars & Princess -2mi DW?

Check-in begins at 4:00 PM.

What time is check-out at Last-Minute Deal! 4BR/4B Disney Villa - Pool, Themed StarWars & Princess -2mi DW?

Check-out is at 10:00 AM.

Where is Last-Minute Deal! 4BR/4B Disney Villa - Pool, Themed StarWars & Princess -2mi DW located?

This family-friendly Kissimmee villa is located in Windsor Hills, within 3 mi (5 km) of Island H2O Live! and Walt Disney World® Resort. Mystic Dunes Golf Club is 2.3 mi (3.7 km) away.

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Last-Minute Deal! 4BR/4B Disney Villa - Pool, Themed StarWars & Princess -2mi DW Reviews

Reviews

10

Exceptional

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

10/10

Cleanliness

Reviews

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

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

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

10/10 Excellent

Sean K., Joliet

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

Best place

Really nice place to stay...all the amenities made it easy to travel. Great location to get to where ever you want!! Highly recommended and will stay there again!!
Stayed 5 nights in Jul 2023

10/10 Excellent

Kevin W.

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

Family Vacation

Amazing place to stay! Great location - close to the parks and a short drive to the beach. The house had everything we needed and more. The kids loved the pool! The neighborhood pool / water park was a nice perk as well. Janette was a great host and extremely responsive. We will definitely be back.
Stayed 7 nights in Jun 2023

10/10 Excellent

Jen B.

Perfect family vacation in a lovely home and resort

This property has everything needed for a family vacation. Loved the decor - the house was very clean kitchen has all you need to cook and a blender for family milkshakes at night!!!! The owners were very responsive to my questions and were very prompt and nice. We’ve been to Windsor Hills Resort before and love the resort. A perfect vacation!!!! Thank you for the wonderful stay in your home.
Stayed 9 nights in Jul 2018

6/10 Okay

Cynthia H.

Liked: Check-in, communication, location, listing accuracy

Good stay 3 to 4 stars depending on the issue

We had a pleasant stay on the property and everything stated on the website regarding the property is true. Unfortunately, the place is not clean thoroughly as we found broken pieces of chocolate in one of the children’s bedroom. I do believe this issue is not specific to the owner but the cleaning service they utilized. The sheets had a heavy body spray odor - again a cleaning issue.
Stayed 4 nights in Feb 2020

8/10 Good

Zach D.

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

Great family place to stay and close to Disney

The property was clean, new and had plenty of space for 8 guests. It was very close to the Disney parks and the drive there from the airport was not bad at all. The community was quiet, safe and kept up very well. A couple of complaints and or negative aspects: The pool was unavailable for most of the day on a Saturday. I talked to the management company and they told me that it gets cleaned on Saturdays, which I did not know about prior to booking (so keep that in mind). The mattress in the master bedroom off the pool was very soft and the sheets were silky, so they kept coming off the bed. From my understanding the other bedroom towards the front of the home has a more firm mattress. The kids said the beds were fine for them in the other rooms. If you are going to go to the Walmart in Kissimmee I recommend only going very early in the morning, or else it is a just a complete nightmare. I chose to drive the extra 10 to 15 minutes to the Publix after one trip to the Walmart. Overall, the pool area was very nice (cool lights and patio, tv), all the TVs worked well in the home. Keep in mind there are strollers, some ponchos left behind and beach towels there in case someone had that question. The washer and dryer worked awesome as well. I would most definitely stay here again.
Stayed 5 nights in Mar 2024

10/10 Excellent

Rich T., Roanoke, VA

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

A very much needed trip to Disney with a nice home to relax at!

I have stayed multiple times at Windsor Hills on previous trips to Disney. This year, due to COVID-19, I was unable to use my DVC points due to banking them for next year. Windsor Hills properties are my next best backup to staying onsite at Disney. The property owners were friendly and responsive throughout the process. Check-in was smooth, we literally gave our license at the front gate and used the door code to open the front door of the home. This is a very nice property overall with only minor cosmetic wear, certainly better than many of the other rental properties I have stayed at. Our first impressions upon entering is that the photos don't quite do justice to how spacious the main area is. The game room was also a hit with our kids. I was pleasantly surprised to find the pool table in good condition as well (this is the first property I stayed at that had a pool table in a usable condition). The included high chair and double stroller were also huge wins for us. I found the kitchen utilities and utensils to be functional and complete. My favorite part of staying here was definitely using the heated pool. The fact that pool heat is included is amazing. It was a cool week by Florida standards and being able to use the heated pool and hot tub really helped soothe the muscles after walking 7-10 miles daily in the parks. We did have issues with the internet not working for a couple days while we were there, which was due to Spectrum Cable. I had some issues reaching the property manager (their voice mail was full) however the owners were responsive within a couple minutes and worked hard to remedy the situation remotely. I also received a pleasant follow up call the following day from the property manager to ensure our needs were met. Cable TV worked perfectly and had an abundance of channels, though it stayed on Disney Jr. HD pretty much the entire time. :) My daughter LOVED the princess bedroom and talks about how awesome it was to have a bunk bed she could sleep on. The Star Wars room is even better in person. Kudos on the creativity involved in decorating these rooms. Overall we really enjoyed our time here at this property and would book it again in the future. This is great value for the money spent, especially with the inclusion of pool heat for the winter months. I wish the Gatt family well with their rental journey and encourage you to smash that Book button if you are on the fence. Have a magical day!
Stayed 10 nights in Dec 2020

10/10 Excellent

erik d.

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

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

10/10 Excellent

Diana P.

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

Great House

We enjoyed our stay here! The house was perfect for me and my family. My girls loved the princess bedroom and the playroom. The pool was very nice and a perfect temperature. It was great to have the floaties for the kids and the fence around the pool. We enjoyed the amenities in the neighborhood as well. This house had everything we needed and more!
Stayed 5 nights in Apr 2022

10/10 Excellent

Verified traveler

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

Amazing stay!!!

Our stay was amazing! The kids loved the pool and the adults loved the hot tub after a long day at the parks. Everything we needed was right there. House was immaculate. We loved the close proximity and quick drive to Disney World. Janette and Brett always responded quickly to any questions and we would definitely stay here again.
Stayed 6 nights in Oct 2021

10/10 Excellent

Zoe W.

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

Your Kids Will Be in Heaven!!

We had such a wonderful stay in this house, and if we go back to Disney anytime soon we will absolutely stay here again! The kids kept whining to leave the parks and go back to the house because it was so much fun! The themed bedrooms are adorable and the playroom is a great bonus. It’s well-stocked with toys for all ages, from baby equipment and toddler toys to X-boxes, foosball, and pool for teens and adults. The pool was great and the hot tub actually got hot quickly, unlike the last house we rented. Everything was very clean and we had everything we needed. We were all sad to leave, and when we drove up to our own house, my 2-year-old started crying and said he wanted to go back!
Stayed 5 nights in May 2021

10/10 Excellent

Maria C.

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

Great Place for a family

I would like to give an extra 5 stars ⭐️ To Janette for a reasonable price and does not charge extra fees for the bbq grill and heating the pool as well not requiring an extra holding deposit. The house was very spacious and the kids loved the themed room and the playroom. Kitchen had everything we needed, all appliances were in good condition. Janette was always available and very attentive. I would go back again.
Stayed 7 nights in Jul 2020

10/10 Excellent

Sawyer H., Michigan

acccurate description, great amenities

We have stayed in some really nice places in Kissimmee, this one was also a winner. We will miss this house and would book it again - it feels like a home. The kids loved their rooms and beds were really comfortable - good mattresses. The kitchen has everything we needed and has new appliances. (we cooked a lot of meals there). Unfortunately, the waterpark wasn't open at the clubhouse but next time!