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Olaf's Endless Summer at Windsor Hills

Photo gallery for Olaf's Endless Summer at Windsor Hills

KITCHEN
Property video
A two-story house with a front driveway, a garage, and a well-maintained lawn.
An outdoor patio with a glass table and chairs, a swimming pool, and a view of the backyard.
A hot tub with a curved edge, surrounded by a brick patio.

Reviews

9.8 out of 10
Exceptional

Highlights

  • Dive into relaxation
    Unwind in the top-rated pool, your perfect spot for relaxation.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
Sleeps 13•4 bedrooms•8 beds

Popular amenities

  • Heated pool
  • Spa pool on site
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View 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

Rooms & beds

4 bedrooms (sleeps 13)

Bedroom 1 - Jr. Royal Princess Suite

2 Single Beds and 1 Double Bed

Bedroom 2 - Motu Magic Haven

1 King Bed

Bedroom 3 - Triple Moon of Endor

1 Queen Bed, 1 Single Bed and 1 Double Bed

Bedroom 4 - Princess Ana’s Crystal Opal Chamber

1 King Bed

4 bathrooms

Bathroom 1 - Jr. Royal Princess Suite Ensuite

Towels provided · Bathtub · Toilet · Shower only · Hair dryer

Bathroom 2 - Motu Magic Haven

Towels provided · Bathtub or shower · Toilet

Bathroom 3 - Triple Moon of Endor

Towels provided · Bathtub or shower · Toilet · Hair dryer

Bathroom 4 - Princess Ana’s Crystal Opal Bathing Chamber

Toilet · Shower only

Spaces

Porch or lanai
Kitchen
Separate dining area

About this property

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!

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Check-out instructions

The host requires you to 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 rubbish
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.

Important information

You need to know

Property # 1289135vb
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the area

Kissimmee

Windsor Hills, a neighbourhood in Kissimmee, is home to this villa. Mystic Dunes Golf Club and Reunion Resort Golf Course are worth checking out if an activity is on the agenda, while those wishing to experience the area's popular attractions can visit Walt Disney World® Resort and Old Town. Travelling with kids? Make time for Disney's Hollywood Studios®, or head to an event or a match at ESPN Wide World of Sports Complex.
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Map
Kissimmee, FL

What's nearby

  • Bonanza Golf & Gifts - 2 min drive - 2.4 km
  • Disney's Animal Kingdom® Theme Park - 9 min drive - 5.5 km
  • Disney's Hollywood Studios® - 11 min drive - 8.8 km
  • Disney Springs™ - 12 min drive - 15.0 km
  • Magic Kingdom® Park - 13 min drive - 15.7 km

Getting around

  • Kissimmee Station - 25 min drive
  • Kissimmee, FL (ISM-Kissimmee Gateway) - 21 min drive

Restaurants

  • ‪Wawa - ‬5 min drive
  • ‪Raising Cane's Chicken Fingers - ‬6 min drive
  • ‪McDonald's - ‬3 min drive
  • ‪Chick-fil-A - ‬5 min drive
  • ‪Satu'li Canteen - ‬7 min drive

Frequently asked questions

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

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

Is Welcome to Olaf's Endless Summer! Last-minute August cancellation Aug 14-21st. pet-friendly?

No, pets are not allowed at this property.

How much is parking at Welcome to Olaf's Endless Summer! Last-minute August cancellation Aug 14-21st.?

On-site parking is available at the property.

What time is check-in at Welcome to Olaf's Endless Summer! Last-minute August cancellation Aug 14-21st.?

Check-in begins at 4:00 PM.

What time is check-out at Welcome to Olaf's Endless Summer! Last-minute August cancellation Aug 14-21st.?

Checkout is at 10:00 AM.

Where is Welcome to Olaf's Endless Summer! Last-minute August cancellation Aug 14-21st. 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.

About the host

Hosted by Janette and Brett Gatt

Host profile image
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.

Why they chose this property

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.

What makes this property unique

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.

Languages:

English

Premier Host

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