Family-friendly holiday rentals in Kissimmee

Sleeps 21|Free Pool Heat|15 min to Disney|Hot Tub

Make memories to last a lifetime in our luxurious seven-bedroom home (sleeps 21) at Orlando's premier vacation community. Enjoy your own Batman cave game room, private pool (heated at no extra charge*), and hot tub. Our 100% Five-Star rating from previous guests and our generous cancellation policy means you can book with confidence. Only 15 minutes to Disney and a short walk to a fabulous resort clubhouse with free access to a lavish pool, kids waterpark, restaurant, playground, gym, and more!

Game & Theater Room, Castle Bunks, Pool & Spa

Vacation at Windsor’s Best located in Windsor Hills Resort just 2 miles from Walt Disney World. This one-story 4 bed, 4 bath vacation villa has everything you need for a wonderful getaway with family or friends. Situated on an elevated corner lot, this spacious villa with it's private pool and spillover spa offers a beautiful view overlooking the resort community. Plus, guests have access to the family-friendly Windsor Hills Resort amenities, including the water park, playgrounds, gym and more.

Winter Sale*Free Pool Heat/WaterPark/Parkings

Welcome home! Spacious and clean 4 bedrooms Townhouse with private pool, located in Storey Lake vacation resort. Free wifi, parking, resort amenities. 15mins drive to Walt Disney Parks, 20mins to Universal Studio, 10mins to Sea World, Water Parks, 25 mins to Orlando Airport, and many shops & retaurants around. This home is degined for funs. The resort offers best in class amenities, including pool, hot tub, water slides, lazy river, splash pad, poolside bar, gym, etc. Enjoy your stay with us!

Experience the Magic of Disney in 8bd/5ba Luxury Villa

New! Experience the Magic of Disney in this 8bd/5ba Luxury Villa! Our 8 bedroom, 5 bathroom pool home is meticulously clean and newly renovated. It offers luxurious & spacious living for families visiting the Orlando area theme parks - it's only a short, 12 mile drive away from Mickey & all his friends, located on the fabulous Champions Gate Resort. Two impressive King Suites, Six awesome themed bedrooms, a home theater, game room and a heated pool await the fun seeking members of your family.

Neverland Found-Minutes from Disney Free Waterpark

Welcome to Neverland Found! This unique property inspires us to never grow up with themed rooms of Peter Pan, The Lost Boys, and Tinkerbell. Our home has 2 Master Suites, a fully equipped kitchen, 5 bedrooms, 5 baths, pool and spa, Pirates of the Caribbean game room, and loft area. Our home is located in the resort community of Storey Lake with access to multiple clubhouses and pools and all of it's amenities. Located within minutes of the theme parks & attractions that Orlando has to offer.

Resort Home| Disney| Solara Resort| w/Pool & Spa

Create unforgettable memories of a lifetime and enjoy a vacation you’ll remember for years to come. This spectacular home is ideally located within the Solara Resort and only 8 miles to Disney, and within a short drive to Universal, Disney Springs, and many beaches! With 4000sqft of luxury living space, a private pool/spa, and a game room for the kids, your family can enjoy the relaxing and fun atmosphere together! Book with us now and give you and your family the vacation you all deserve.

Magical Hideaway - 15 min to Disney - Storey Lake

Welcome to The Magical Hideaway! Bring your family an immersive experience into our Disney-themed vacation home in Storey Lake community. Our home includes a specially themed Princess and Superhero rooms. Dive into fun at the resort pool with a lazy river and water slides. Enjoy your own plunge pool and our photo-op green wall. Entertainment includes 4 Roku TVs, Disney board games, and puzzles. We've also got you covered with a stroller, crib, and highchair provided.

No Airbnb Fee | Newly Renovated 4BR w/ Pool!

**We offer EV Charger for FREE!!! The magic of Orlando starts at home! This incredible house has much more than you need; it has everything you WANT! We offer guests comfort, convenience and an amazing experience!! Transparency and communication is very important to us! We want to make it clear, that we are here at your disposal for any doubts or suggestions. We can't wait to have you here enjoying peace and quiet and having lots of fun!

Storey Lake 5BR Villa w. Pool&Spa & Water Park

Enjoy comfort, style, and location at this 5-Bedroom / 5-Bathroom single-family resort pool home in Storey Lake. Features 2 King en-suites, 1 King bedroom, Star Wars and Mickey themed bedrooms, fully stocked kitchen, open living area, and private pool and spa (hot tub). Resort amenities include pools, lazy river, slides, splash pad, fitness center, and sports courts—all minutes from Disney, Universal, and shopping.

Home 6 BDR at Solara Resort/Private Pool LED

The Space * Accommodates: 16 * Bedrooms: 6 * Bathrooms: 4.5 * Property type: Luxury Villa * Location: Solara Resort * ONLY 0.2 miles away from The Clubhouse! * 12 miles from Magic Kingdom * 8 miles from Animal Kingdom * 16 miles from SeaWorld * 21 miles from Universal Studios * Property and resort close to the US 27 highway where some restaurants, market, gas station, pharmacies are located.

5BD Windsor Westside Private Pool (WW 8920)

We invite you to our Beautiful 5 Bedroom / 5.5 Bathroom with private swimming pool home and all the amenities necessary for your family and friends to spend a precious and memorable vacation in Orlando. House is part of the newest phase (3) of the Luxurious Windsor at Westside Resort. Guests will have full access to club house amenities.

202_Magical and Cozy 2BR minutes from Disney

The ultimate choice for your Orlando getaway! Our cozy apartment is thoughtfully designed to make you feel right at home, with all the comforts and amenities you need. Plus, enjoy complimentary access to the waterpark – the perfect way to relax and have fun after a day of exploring the parks or shopping in Orlando!