Villa in Windsor Hills, FL
13 guests · 4 bedrooms · 4 baths
Reasons to book
Guests love it hereGuests give this property a top rating
Well priced for this locationPriced under area average
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental
About this villa rental
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!
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!
Amenities at Olaf's Endless Summer at Windsor Hills
Non-smoking
No pets allowed
Family friendly
Map of Windsor Hills, FL
Ratings and reviews
10 / 10Outstanding·Jun 2026
Amazing home. Amazing host. Amazing trip. We have stayed at Windsor Hills homes, townhouses, and condos for every WDW our family has had since 2005 and this was one of our best experiences! :)
10 / 10Outstanding·Jun 2026
We enjoyed our stay immensely from start to finish.......house contained everything a family could need for an excellent relaxing stay and we would therefore recommend it to future clients who may be considering staying.The clubhouse with slides, pools, etc just down the road, a very short distance was extremely pleasant, as was the games room in the garage and for some, the large TV under the lanai by the pool.We couldn't fault anything on our visit but we would recommend a change of sun beds by the pool as the present ones are a mite uncomfortable with no padding or cushions.Thanks for the stay .....we would definitely recommend it to our friends and family
10 / 10Outstanding·Jun 2026
It was a wonderful house and a perfect stay!
6 / 10Average·Jul 2026
The biggest area for improvement is the cleaning. While the surfaces appeared clean, it didn't seem like the home receives regular deep cleaning. The ceiling fans were so dusty that dust flew off when we turned them on, making them unusable. We also found a dead cockroach in one of the front bedrooms that should have been caught during cleaning. With frequent guest turnover, deeper cleaning should be a priority. The welcome packet also needs updating. It stated there was only a standard coffee maker, so we bought a small Keurig, only to find the coffee maker actually has a Keurig attachment built in. Having accurate information would have saved us the unnecessary purchase. Another suggestion is to provide more guidance for guests who are not traveling with a car. The welcome information seems to assume everyone will have their own vehicle. We arrived by Uber and planned to spend some time at the clubhouse before check-in, only to learn that the clubhouse does not assist with luggage storage or transportation. We had to keep our luggage with us until 4:00 p.m. and then arrange our own way to get it to the house, which is not within easy walking distance. The host did have the property managers assist us, which we appreciated, but knowing this information ahead of time would have allowed us to plan differently Overall we enjoyed our stay, but with improved deep cleaning and more up-to date, detailed guest information, this would be an even better experience.
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Top rated by guests
9.6Outstanding
(27 Ratings)
"Amazing home. Amazing host. Amazing trip. We have stayed at Windsor Hills homes, townhouses, and condos for every WDW our family has had since 2005 and this was one of our best experiences! :)"
Kristie D.Don't miss out! Price and availability may change
