Olaf's Endless Summer at Windsor Hills

We’re a family of seven with five kids ranging from 7 months to 17 years—so yes, we know a thing or two about chaos, snacks, and the magic of a well-timed nap. Brett and I have been visiting Florida since we were kids, and now we’re passing that pixie dust on to our own crew. Olaf’s Endless Summer is our way of sharing the joy, laughter, and occasional sunscreen mishap that comes with a great family vacation.

Over the years, we’ve stayed in all kinds of places—from “barely Belle-worthy” to “almost Cinderella’s castle”—and we’ve built our home to meet the real needs of families. With five kids, we know what matters: space, safety, and sanity. That’s why our home has four bedrooms, four bathrooms (no sharing—hallelujah!), and a single-story layout. No stairs, no elevators, just park and walk in. Whether you’re wrangling toddlers or traveling with grandparents, it’s smooth sailing from check-in to checkout.

We’ve added themed rooms that make bedtime feel like an adventure—Star Wars™, Moana™, Princesses, and Frozen. And yes, the triple-decker bunk bed is real, and yes, it’s awesome. We also stock strollers, highchairs, wagons, playpens, and a toy room so full it might just rival Andy’s from Toy Story. Plus, we’ve got a BBQ grill on the honor system—because nothing says vacation like dad flipping burgers while humming “Hakuna Matata.”

We’re not just hosts—we’re your behind-the-scenes crew. We have a great management team, but we’ll also pick up the phone if you need help registering someone at the gate, making a last-minute change, or figuring out what to do your first night. Brett’s “Dad’s First Day Check-In List” is available upon request—complete with snack stops, pool priorities, and a reminder to charge your phone before 1,000 castle pics.

We want your first trip to be magical—and your second, third, and fifteenth too. So come stay with us, make some memories, and let Olaf’s Endless Summer become part of your family’s happily ever after.

We want you to be part of our story—one filled with magic, memories, and meaningful moments. With over 20 years of hosting experience and a deep love for creating welcoming spaces, we’ve poured our hearts into making Olaf’s Endless Summer a place where families can truly relax and reconnect. Every guest receives the same care and attention we’d give if we were staying there ourselves.

Located in the renowned Windsor Hills Resort—just 2 miles from Disney World—our home offers unbeatable value, comfort, and convenience. As the closest gated vacation community to the parks, Windsor Hills features spacious rentals, private pools, and themed rooms that feel like home. Guests enjoy resort-style amenities including a heated lagoon pool, water park, movie theater, and sports courts—all with no resort fees and free parking. With 24/7 security and family-friendly features throughout, it’s a safe, stress-free haven after magical days in the parks.

Olaf’s Endless Summer is professionally decorated and designed with families in mind. You’ll find immersive themed bedrooms inspired by Star Wars™, Moana™, Disney Princesses, and Frozen—each one crafted to spark joy and imagination. After a day of adventure, unwind with a nighttime swim in your private pool while watching your favorite Disney movie under the stars. If you're lucky, you might even catch a glimpse of the nightly fireworks from the parks! And when the fun isn’t over, head to our “Under the Sea” games room for more playtime magic.

We’re always adding new touches to keep the experience fresh and exciting. Inspired by Walt Disney’s words—“Disneyland will never be completed. It will continue to grow as long as there is imagination left in the world”—we embrace that same spirit of creativity. Our latest upgrade? Custom Mickey Mouse Ear Lights over the breakfast bar, adding a playful glow guests of all ages can enjoy.

Come stay, and let your story begin.

Olaf’s Endless Summer isn’t just one of the best homes in Windsor Hills (WH)—it’s one of the smartest choices for families.

The 4-bedroom, 4-bathroom single-story layout means NO stairs, elevators, or shared bathrooms. Park right outside and walk straight in, making arrival and daily routines effortless. As a parent of five, I know how valuable that is—no worrying about toddlers climbing stairs or grandparents navigating them. Each bedroom has its own private bathroom, so whether you're traveling with another family or bringing along grandparents, everyone gets their own space and privacy.

Our themed rooms are built with flexibility in mind. The Star Wars™ room features a custom triple-decker bunk bed that sleeps several kids, while the Princess room includes a pull-out trundle for extra space. Kids can each have their own bed, and adults still enjoy their own quiet retreat.

It’s the little things that make a big difference. We provide a BBQ grill on the honor system (if it’s empty, please refill). We also stock highchairs, strollers, playpens, wagons, and a toy room full of fun, so you don’t have to pack or rent bulky gear other homes charge extra.

We don’t just want your first trip to be magical—we want to welcome you back year after year. WH is full of mini adventures: join the DJ Hula Hoop dance party (our daughter is undefeated after 15+ rounds!), shoot hoops, explore the parks, search for Sr. Winston from the lookouts, enjoy crafts in the lobby, play at the playgrounds, splash at the water park, or lounge in the heated lagoon pool. We’d be honored to be part of your story.