Family-friendly vacation rentals in Kissimmee

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

Indoor spaces · Family · Layout

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!

Kitchen · Family · Comfort

Encanto at Emerald Island-Pool House by Disney

POOL HEATER OPTION!! Make some memories at this unique and family-friendly place. A guarded Resort- neighborhood awaits! As you enter this magical place you will fall in love with the unique landscaping full of palm trees surrounding the neighborhood. This secluded place has everything you need! 5 star location, security, private pool, and also a clubhouse with many activities for the young ones. You will be next to restaurants, shopping and more. Only 3 miles aways from Disney's exit & parks!

Kitchen · Family · Layout

Themed Disney Villa | Pool | Arcade | Resort ºoº

Stay in a luxury Disney-themed home just minutes from the parks. Perfect for large families and groups, this spacious retreat features a private heated pool and spa, outdoor kitchen with free propane, Mario Kart arcade game room, themed bedrooms, gourmet coffee, fast WiFi, smart TVs, and premium streaming. Enjoy full Windsor Island Resort access with a water park, lazy river, slides, and clubhouse. Loved by guests with over 100 5-star reviews. Let us give you a vacation within your vacation.

Indoor spaces · Family · Cleanliness

Brand New - 12br - Sleeps 34 - Theatre/Arcade/Pool

**Experience the ultimate Disney vacation in this spacious 12-bedroom home that sleeps up to 34, just minutes from the parks. Perfect for large groups, it features themed kids’ rooms, a private pool, hot tub, and outdoor kitchen. Enjoy a Transformers game room, private movie theater with reclining seats, and a professional poker table. With cozy bedrooms and fun themes like Minions and Scooby-Doo, this home is perfect for unforgettable family vacations and group getaways.

Kitchen · Indoor spaces · Value

10 Min to Disney | Kings | Heated Pool | Games

✨ Perfect family getaway just minutes from Disney magic! ✨ This spacious 4-bedroom home sleeps 9 and features 2 king beds, 4 full beds, and 1 twin, plus fun Mickey Mouse & Minion themed rooms kids love. Unwind in your private screened pool, enjoy the game room with arcade games, ping pong, foosball & pool table, or relax with cozy board-game nights. 🏰 Animal Kingdom 10 mins Epcot & Hollywood Studios 15 mins Book now and start making unforgettable family memories!

Family · Indoor spaces · Layout

9 Themed Bedrooms, Pool & Jurassic Theater

Pool, fire pit, and nine themed bedrooms, from the Dragon Cave and Avatar Forest to Moana Island, bring the whole group together under one roof. Kids can dive into the Jurassic theater, Cars game room, and resort access, while adults enjoy a stay that feels easy and relaxing. Perfectly set up for days at the theme parks and evenings everyone will actually enjoy, this home makes every moment count. Book your stay and turn Disney days into lasting family memories.

Kitchen · Family · Outdoor spaces

4BR Disney & Universal Themed Villa Reunion Resort

Welcome to our newly remodeled 4BR/4BA luxury villa in Reunion, designed for families and groups seeking comfort, style, and a magical Orlando escape. Enjoy brand-new furnishings, modern finishes, Toy Story and Mickey themed bedrooms, a spacious open living area with massage chair, and a fully equipped game room featuring air hockey, arcade basketball, and PlayStation. Relax in your private screened pool with optional heating after unforgettable park days.

Indoor spaces · Family · Cleanliness

Pixie Palace Near Disney Home Arcade Private Pool

Experience the magic at Pixie Palace! Luxury Disney Villa with FREE Pool Heat, BBQ & Tesla/EV Charging! This immaculate 8-bedroom, 5-bath retreat is newly renovated with beautifully themed rooms, a gourmet kitchen, spacious gathering areas, two walk-out master suites, a private home theater, and a sparkling pool & spa. Perfect for large families and groups, just 15 miles from Walt Disney World. Create magical memories that will last a lifetime!

Family · Indoor spaces · Comfort

No Airbnb Fee | Luxury 7BR w/ Cinema & EV Charger!

**We offer a FREE EV Charger! We know that this may be a lot to read, but we suggest that you read everything and ask any questions you may have to see if it really is the right place for you and your group! :) Transparency and communication is very important to us! We want to make it clear, that we are here available, for any questions or suggestions.

Kitchen · Indoor spaces · Backyard

2026 Themed NEW 08 Bedrooms At Solara Resort

Our vacation homes will bring you to experience beyond a simple stay. You will be near the most famous themed parks in the world while feeling the comfort of your home, plus having the highest standard of luxury and modernity, with everything a vacation home in Orlando can offer you.

Family · Indoor spaces · Cleanliness

Magical Disney Family Escape with Pool & Game Room

OpenAGetaway Properties invites you to experience an immersive, family-friendly getaway at Mickey House. *Newly remodeled villa *Private villa pool *Superhero-themed arcade room *Desirable Windsor Resort Neighborhood *5 minute walk to the full-service resort & clubhouse

Indoor spaces · Family · Amenities