Family-friendly holiday rentals in Kissimmee

Top Floor, 3bd, FREE Clubhouse, Kids Room, Disney

*BRAND NEW CONDO* This penthouse vacation condo offers stunning pool views, accessible via an elevator, is ideally situated just moments away from Walt Disney World, restaurants and shops. Boasting 2 bedrooms, 1 KidsRoom and 2 bathrooms, it's the ultimate family retreat, ensuring a magical vacation. Inside, you'll find a dedicated Kids' Room and an exciting Arcade, while the kitchen adds to the fun with its unique features, including a Waffle bar and Popcorn corner for the whole family to enjoy!

Indoor spaces · Family · Bathroom

WaterPark+Arcade+KingBed+Hot Tub+NearDisney

Family-Friendly Orlando Vacation Home Near Disney & Universal ✨ Welcome to your dream getaway! This spacious 4-bedroom, 3-bathroom villa is perfectly located just 25 minutes from top attractions. With themed bedrooms, first floor bedroom and bathroom and access to resort-style amenities, our home is designed for unforgettable family vacations.🌟 Why Guests Love It: •Themed Bedrooms: Lion King mu •Resort-Style Amenities: Relax in the tropical pool, hot tub, fitness center, clubhouse, and arcade.

Family · Indoor spaces · TV

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 · Parks

10 Minutes to Disney | Heated Pool, Arcade, Kings

🏡 Tucked inside a gated community near Kissimmee’s top attractions, this bright, themed home is made for memorable family getaways. Enjoy friendly competition in the game room, unwind in the heated private pool (available upon request), or relax on the covered patio beneath the Florida sun. Just 11 minutes to Fun Spot America, 11 minutes to Old Town, and 12 minutes to Disney World, it’s the perfect home base for your Florida adventure. Book now and start creating unforgettable memories!

Indoor spaces · Family · Bathroom

OMG! Disney Area, Movie Theater, Game Room & Pool!

"Guest favorite" - This home is in the top 5% of eligible listings based on ratings, reviews, and reliability. Comfort and Space in an Elegant home with a lot of amenities, 4Bed/3Bath. Private Movie Theater, Game Room, Pool and Themed Rooms. A well equipped Kitchen, Laundry, 3 parking spaces, WiFi, Smart TVs. Located at Crystal Cove Resort, a gated community, close to Disney. Few minutes to Walmart, Target, Sams Club, Publix, Outlets, Restaurants, Disney, Sea World, OCCC, EPIC and Universal.

Kitchen · Indoor spaces · Parking

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!

Kitchen · Family · Cleanliness

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.

Kitchen · Indoor spaces · Value

Magical Pool Villa-close to Disney Game/movie Room

The magic starts the moment you walk through the door—and the memories will last a lifetime! ✨ Our themed vacation home features Mickey Mouse, Toy Story, Frozen, Star Wars and Minion rooms with motion-activated songs, UV artwork, and LED lighting. Enjoy a private pool with color-changing lights, BBQ area, sun loungers, and a fun-filled game room with air hockey and arcade games. Designed to delight kids and adults alike with immersive sights, sounds, and magical details throughout the home!

Indoor spaces · Family · Condition

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.

Family · Kitchen · Parking

5BR Disney Pool Villa | Arcade + Spa | Sleeps 11

Make your Disney vacation part of the adventure! 🏰✨ Our spacious 5BR villa sleeps 11 and is made for family fun. Enjoy your own private pool & jetted spa, an air-conditioned private arcade, and themed bedrooms with hand-painted murals. 🐭 Near Disney & Universal 🏊 Private Pool + Jetted Spa 🕹️ Private Arcade 🛏️ 5BR | 2 Kings | Sleeps 11 🏝️ Resort Amenities 👨‍🍳 Stocked Kitchen 🛜 Fast WiFi 🧹 No Cleaning Fee The perfect home base for park days, pool days & family memories!

Kitchen · Family · Getting around

Super Mario's Sky Suite - Epic Universe 3 BD SUITE

Welcome to your ultimate Nintendo getaway where every room is artfully and thoughtfully designed with a unique Super Mario theme. From custom decor to playful details, every corner is a tribute to the beloved world of Mario and friends. With classic Nintendo consoles at your fingertips, you’ll have everything you need to relive your favorite gaming memories in style. Unwind, play, and immerse yourself in the colorful world of Nintendo - TRUE SUPER MARIO ENTHUSIASTS ONLY :)

Indoor spaces · Family · Parks

Royal Retreat Disney Themed Pool Home, Arcade, Theater

Welcome to The Royal Retreat. Located just 10 miles away from the entrance of WDW, our rental is the perfect place to stay for your Disney vacation. Our 5 star home features 8 themed bedrooms and 5 bathrooms, a fully-equipped kitchen, private heated pool, private arcade, home theater & BBQ! Free Pool heat & the 1st tank of propane for the BBQ are included. Booking with us includes full access to the Champions Gate Clubhouse, Oasis Resort and Retreat Club!

Family · Kitchen · Access