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.
