Family-friendly holiday rentals in Kissimmee

4BRThemed/Pool/Near Disney/PetsOk/Free BBQ&Resort

Discover luxury and convenience at our 4-bedroom townhome in Paradise Palms Resort. Enjoy a private pool, lakeview sunsets, and themed rooms featuring Moana, Avatar, Mario Bros, and Roblox. With two elegant king suites, world-class resort amenities, and only 9 miles from Walt Disney World, it's the perfect Orlando getaway. 9 miles to Walt Disney World 🎢 16 miles to Sea World 19 miles to Universal 27 miles to MCO (Orlando International Airport) Join Us for a Disney Adventure! Learn More Below!

No Airbnb Fees! Pool/ SPA/Game Room /Resort 242661

Unable to book this house? Don't worry! Check my profile for similar homes that might suit your needs WE HAVE A 24/7 CUSTOMER SERVICE! Escape the routine of visiting the parks every day and step inside of this 3,014 sqft house with 5 bedrooms, private pool, SPA and a game room with arcades specially designed to entertain your family. You can also have some fun at the Clubhouse, which offers a bar/restaurant, a big pool with water slides, a lazy river, a spa, a gym, a playground, and mini golf.

Kids Love It More Than Disney! Pool + Games

Happy 2026 from Kissimmee! Westside Villa has just a few openings - snag it while you can! -20 minute drive to all Disney Parks -Private, heated pool; gas grill; EV charge on-site -Modern arcade: racing simulators, virtual reality, vintage games -3 king size suites with smart TVs; dedicated work space -2 pack-n-plays, highchair, strollers, wagon -Resort access: lazy river, splash pad, tiki bar, fitness center Arriving early in the day or leaving late? Ask about our half day add-on, if our cal

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!

Resort Home 3.5 miles to Disney with home theater

We welcome you to stay in our home located in the Windsor Hills community with a water park, slides, theatre and so much more! The house is just 3.5 miles from Disney’s Animal Kingdom. Our home has 6 large bedrooms including laundry in the home, an 8 seat home theatre, TVs in every room, a large swimming pool & spa with a large patio cover, plus a large kitchen fully equipped with everything you need for your stay. Please message us if you have any questions, we look forward to hosting you!

Magical Family Fun House Near Disney Luxury Villa

Experience the Magic of Disney in our Luxury Villa! BBQ Included! Tesla / EV Charging Station! Free Pool Heat! Our private 8 bedroom, 5 bathroom one of a kind pool home is meticulously clean & newly renovated. Newly remodeled kitchen and themed rooms, and richly-appointed spaces include large gathering areas, a bright, professional-grade kitchen, spectacular dining room, 2 walk-out master suites, a home theater & Tesla / EV Charging Station! Sparkling pool and spa. Only 15 miles from Disney

Free Waterpark, Fantasy World, The Mickey House

It is a beautifully decorated house located a few minutes from Disney, Universal Studios, Sea World, and other attractions. Close to restaurants, Walmart, Target, Publix, and other stores. It is a nice and fun resort, with free access to our gorgeous pool area, waterslides, lazy river, and sports courts. The pools and lazy river are heated and open all year long. Shuttle to major parks is available and must be paid separately at the front desk. Kids 3 years old and under ride free.

Heated Pool 15 Minutes to Disney PS5 l Switch

Spacious 4BR Home with a Private Heated Pool – 15 Minutes from Disney! Enjoy a large south-facing pool, Propane grill, Smart TVs with Disney+ in every room. Nintendo Switch in Living Room and an 85" screen with a PS5 in a temperature-controlled garage / game room. Fast WiFi, shuffleboard, pool table and plenty of board games. 🌴 Outdoor Fun Patio Seating for 14 + two lounge chairs. Propane Grill: $50 for length of stay Pool heat: $200 per stay (24-hour notice)

Enchanted Home Near Disney • Arcade Room

Welcome to our enchanting 3-bedroom, 3-bathroom haven, meticulously designed to embrace your family's comfort and imagination! Step into themed suites straight out of your favorite stories, including Toy Story and Mickey Mouse. With a spacious capacity for up to 10 guests, your Disney adventure begins right here! The following extra services include additional costs: Grill Early Check-in Late Check-out

Disney-Themed Home w/ Game Room & Private Hot Tub!

Welcome to our beautiful home in Solterra Resort, a new luxury gated community located in Orlando, just 22 minutes from all Disney theme parks! Enjoy a recreation-rich lifestyle with majestic amenities including a Lazy River, open daily with over four rolling acres of tropical recreational space including swimming, tennis, a jacuzzi, a big waterslide, and even a poolside restaurant!

6BR Disney Villa | Pool, Spa & Theater | Sleeps 14

Spacious 6BR home in Windsor Hills Resort—just 5 mins to Disney! Enjoy a private screened pool & spa, home theater, themed rooms, full kitchen, and smart TVs throughout. Resort perks include a water park, arcade, gym, and more. Sleeps 14 with plenty of room for the whole family. Gated community, free Wi-Fi, and 24/7 guest support. The ultimate Orlando getaway starts here!

New Themed home w/pool in Margaritaville Poco Loco

New Listing!!! Enjoy introductory rates at this beautiful luxury resort! Relax with the whole family at this peaceful and fun place to stay. Enjoy your own private pool.