Family-friendly holiday rentals in Kissimmee

4.75 out of 5 average rating, 138 reviews

No Airbnb fees! Home Theater! Pvt Pool/ Spa 278291

Unable to book this house? Don't worry! Feel free to check my profile for similar homes that might suit your needs WE HAVE 24/7 CUSTOMER SERVICE Disney is just a short 8-mile drive away Tired of visiting the parks every day? Step inside this beautiful thematic 2,169 sqft house with a private pool, spa, BBQ, Star Wars themed movie theater, and a Mario Kart game room complete with arcades, pool table and foosball table all designed for family enjoyment! Make your vacation truly unforgettable!

A themed game room showcases a Batman-inspired design with a bright yellow slide leading to a two-level play area. An air hockey table is positioned prominently, surrounded by stylized dark walls, creating an immersive gaming environment.

4.99 out of 5 average rating, 154 reviews

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!

A themed movie theater room is presented with dark walls and vibrant purple lighting. Comfortable lounge seating is arranged towards a large screen, showcasing a colorful animated scene. Mario-themed decor and graphics adorn the walls, creating an engaging atmosphere for family movie nights.

5 out of 5 average rating, 105 reviews

5BR Mario& Princess Peach•Pool•Theater•Free Resort

Escape to an unforgettable Disney Adventure, just 9 miles from Walt Disney World! Perfect for Mario Bros, Moana & Princess Peach fans. Enjoy themed rooms, cozy bedding, and a private pool. Indulge in movie nights in our Mario Bros theater! Bring the whole family, including pets, and make magical memories. 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 an Unforgettable Disney Adventure! Learn More Below!

Superhost

A screened-in patio features a private swimming pool and hot tub, surrounded by a tranquil lake view. String lights create a soft illumination against a colorful sunset sky, enhancing the peaceful outdoor setting.

4.85 out of 5 average rating, 185 reviews

10 min Disney | Lakeview Hot Tub, BBQ | Game Room

Welcome to your family's next dream vacation! You'll be located only 10 minutes from Disney, 20 minutes from SeaWorld, 25 minutes from Universal, and just 30 minutes from Orlando International Airport (times vary by traffic). When you want to unwind at the house, you have a fully loaded game room (billiards, air hockey, foosball, and more!), private swimming pool and hot tub with a breathtaking lake view, BBQ grill, ultrafast Wi-Fi, and complimentary Disney+ on each of the five 4K Smart TVs.

4.86 out of 5 average rating, 110 reviews

8Bd 4K Movie Theater 155 Inch Screen Pool & Spa

A vacation home that takes your entertainment seriously! That’s our 8-bedroom villa in Emerald Island Resort at 3 miles from Disney… Ready to enjoy themed bedrooms, a premium private movie theater with a 155-inch screen, 4K projector, 5.1 surround sound, and a PS5 for gaming? Relive your favorite films in stunning quality, just like in the best movie theaters. Private Pool and Spa will make your vacation unforgettable! We’re ready for families and groups, to offer fun, comfort, and luxury.

5 out of 5 average rating, 59 reviews

An inviting outdoor area showcases a private pool and spa, surrounded by lounge chairs and colorful beach balls. A dining table and large gas grill offer options for outdoor meals. Lush greenery lines the fence, providing privacy and a vibrant backdrop against a sunny sky.

Home in Four Corners

Gorgeous 5BR at Encore Resort next to Disney - 305

Modern 3,000sf luxury home, with 5 bedrooms, at world's renowned Encore Resort at Reunion. Featuring 5 bedrooms, 5 1/2 bathrooms, a game room, a beautiful backyard, a private pool and spa. 6 Minutes away from Super Walmart and Publix supermarket 15 Minutes away from Disney Parks 15 minutes away from Disney Springs 15 Minutes away from Premium Outlets 20 Minutes away from Universal Studios 20 Minutes away from International Drive attractions *PLEASE MAKE SURE TO READ THE HOUSE RULES*

A private heated pool is set within a screened enclosure, surrounded by a patio area. Two blue chairs and a white lounge chair are positioned nearby, with lush greenery visible beyond the pool. The clear water reflects the sky, creating a serene atmosphere.

4.99 out of 5 average rating, 160 reviews

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)

4.96 out of 5 average rating, 127 reviews

Home in Davenport

Magical 2 pool-Spa & Game Room Villa near “Disney”

Looking for stay away from the crowd but yet close to Disney ? This private pool themed home is perfect to complete your Dream Disney family vacation you always wanted. 15 miles /Magic kingdom -13 miles from Disney springs -15 miles from Epcot center -25 miles / 30 Universal Studios Make your stay Magical with our custom made themed rooms Star Wars play area and kitchen Romantic master Arabian night Avatar pandora Moana bedroom Just less than 2 miles from I4 hw

5 out of 5 average rating, 61 reviews

An engaging kids' bedroom is displayed, featuring a jungle-themed design with a playhouse and a slide. The room showcases vibrant wall art, while colorful bedding and fun decor invite imaginative play. A covered sleeping area offers cozy bunks, completing the adventurous atmosphere.

Home in Osceola County

Your Dream Vacation—Disney Magic Brought to You!

Welcome to Your Custom-Crafted Dream Vacation! Among countless vacation rentals, our uniquely designed home offers an unparalleled experience perfect for your family's ultimate getaway. Every detail is thoughtfully curated to create a relaxing haven for you, while your kids discover excitement around every corner, keeping them entertained throughout your stay. We've brought the magic of Disney to you, ensuring unforgettable family memories that will last a lifetime!

A vibrant games room is equipped with various arcade machines, including SpongeBob Racing. A massage chair is positioned nearby, while a theater room features plush seating. An outdoor space highlights a screened-in pool area surrounded by palm trees, visible through large windows.

4.99 out of 5 average rating, 247 reviews

Windsor Orlando Private Arcades,Theater,Pool-Spa

Orlando, Disney, Arcade, Movie Theater, Massage Chair, Pool, Hot Tub, 2 King Beds, Kids Bunk Bed, Kissimmee. Upgraded games room IN the private home, theater for evenings home and your private lanai with pool and hot tub. Choose from including Pump It Up dance, Sponge Bob Racing, NASCAR racing, Legends 3, Pac-Man's Arcade Party, an 80-inch TV, and an Xbox 360. Watch your favorite movies on the 92-Inch projection screen, surround sound, and stadium style seating.

5 out of 5 average rating, 5 reviews

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.

4.99 out of 5 average rating, 139 reviews

A vibrant hallway is adorned with deep blue walls, featuring golden stars and a playful Mickey Mouse theme. A picture of Mickey Mouse in a wizard hat is displayed on the wall, complementing the themed decor. A stylish side table is positioned against the wall.

Villa in Four Corners

Mickey Fantasia Family Friendly w/accessibility

This home was designed with the idea of imagination in mind. Imagination can take you to places you otherwise could have only dreamt of being in; Walt Disney himself said, "If you can dream it, you can do it". The vibrancy and life that fills this house represents imagination. When you set foot in this house, the real world fades away. Here, life can be a rainbow. People of all abilities are welcome to sing, dance, and have fun here.

Popular amenities for Kissimmee family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

The single-story home features a welcoming façade with a brick accent. Lush palm trees frame the entrance, which is highlighted by large windows allowing natural light to filter inside. A manicured lawn and a decorative white planter add charm to the front yard.

4.95 out of 5 average rating, 243 reviews

Disney Orlando vacation home with private pool 2

A screened-in pool area features a clear blue pool with floatation devices, surrounded by a sunlit deck. A Tiki bar with seating stands to one side, while lounge chairs are arranged along the edge. Lush greenery is visible beyond the enclosure.

4.95 out of 5 average rating, 122 reviews

Disney Retreat | Huge Pool with Spa | 2 King beds

4.93 out of 5 average rating, 105 reviews

Lakeside Paradise, 15 min Disney + Saltwater Pool

4.99 out of 5 average rating, 164 reviews

The collage showcases various areas of the lakeside home. Highlights include a private patio dining set, a resort-style pool, a comfortable living space with a dining table, and vibrant bedrooms featuring bunk beds and colorful decor. The picturesque lake view complements the outdoor spaces.

Townhouse in Kissimmee

Lake View - 5 Miles to Disney!

A vibrant outdoor area features a sparkling saltwater pool with fountain jets and colorful LED lighting. A large screen displays a movie, surrounded by lounge chairs. The area is enhanced by string lights and a cozy seating arrangement, creating an inviting space for relaxation and entertainment.

4.87 out of 5 average rating, 243 reviews

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

A game room features various entertainment options, including a treadmill, exercise bike, and classic arcade machines. The decor showcases a 'Star Wars' theme with vibrant blue lighting and dark walls, creating an inviting atmosphere for guests to enjoy recreational activities.

4.93 out of 5 average rating, 108 reviews

Luxury Villa! /Game Room/ Pool Heater

A home theater room is equipped with red stadium seating for eight, positioned toward a large screen displaying vibrant visuals. An arcade game machine is set beside the screen, with ambient blue lighting accentuating the dark walls, creating an engaging entertainment space.

4.87 out of 5 average rating, 144 reviews

Resort Home 3.5 miles to Disney with home theater

5 out of 5 average rating, 115 reviews

The image features a private pool surrounded by lounge chairs, with a basketball hoop and a lush green backdrop. An entertainment area is visible in the foreground, showcasing a game table, a digital pinball machine, and a large screen for movies and games, including a fun tube slide.

Home in Four Corners

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5

Family- and pet-friendly home rentals

A modern two-story house is showcased, featuring a bright exterior and a spacious driveway. Lush green grass surrounds the property, while palm trees add a tropical touch. Large windows on the upper level allow for ample natural light, highlighting the clean lines of the architecture.

4.96 out of 5 average rating, 127 reviews

Villa Resort Club

The exterior of a single-story home is presented, featuring a paved driveway leading to a two-car garage. Lush green grass surrounds the house, and palm trees are positioned near the entrance. A colorful sunset sky provides a picturesque backdrop.

4.99 out of 5 average rating, 149 reviews

Beautiful home. Private pool. Close to Disney!

A game room is showcased with a blue pool table at the center. Colorful wall murals feature animated scenes, including boats and castles. Comfortable seating is arranged nearby, and multiple screens display entertainment options. The space is designed for both relaxation and fun.

4.87 out of 5 average rating, 100 reviews

EPIC 8BR Theme Villa ~ Sleeps 19 ~ Close to Disney

A home cinema room features a large flat-screen TV displaying a film scene. The walls are painted blue and red, and plush seating is arranged in front of the screen. Decor includes framed posters and a Mickey Mouse silhouette, creating an engaging entertainment space.

4.86 out of 5 average rating, 441 reviews

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

An outdoor dining area features a large, custom-built farmhouse table surrounded by benches. Refreshments and fruit are displayed on the table, with a private pool visible in the background, enclosed by a screened lanai. Lush green grass complements the serene atmosphere.

4.96 out of 5 average rating, 227 reviews

★Completely Renovated★ 3 mi to Disney+Free Resort!

4.86 out of 5 average rating, 102 reviews

4m Disney Sun, Free Snacks, Golf, Pool• Spa• Games

A vibrant children's bedroom is adorned with a whimsical mural depicting fairytale scenes. Two beds with elegant metal canopies frame the room, each dressed in colorful bedding featuring princess themes. Natural light filters in through a window, complementing the playful decor.

4.95 out of 5 average rating, 172 reviews

🏰 Disney Princess Crownhouse! Closest to Disney!

4.99 out of 5 average rating, 108 reviews

Villa in Davenport

Amazing Villa near DisneyWorld FREE heated-pool

Family-friendly home rentals with a pool

A sparkling private pool is surrounded by lounge chairs and tropical landscaping, providing a relaxing outdoor space. A gaming room features vibrant blue lighting, a pool table, and arcade games. A colorful playroom, equipped with a slide and play equipment, invites children to enjoy indoor activities. A movie theater room displays plush seating and a large screen for film viewing.

4.9 out of 5 average rating, 50 reviews

House Resort at Encore Reunion - Disney

5 out of 5 average rating, 17 reviews

Luxory/Championsgate/private Pool/2 gulf courses

5 out of 5 average rating, 12 reviews

House located 10 minutes from the parks.

An open-concept living area features a large sectional sofa in soft gray, arranged around a circular coffee table. A contemporary fireplace is integrated into the wall, providing a focal point. Glass doors lead to the outdoor pool area, enhancing natural light throughout the space.

5 out of 5 average rating, 71 reviews

Luxury Home w/ Pool & 6 Beds near Disney

5 out of 5 average rating, 25 reviews

2602SN - Stunning Home 5 Ensuites Near Disney

Superhost

Townhouse in Kissimmee

5 out of 5 average rating, 6 reviews

4 Bd / 3 Ba / Sleeps 11/ Storey Lake Resort

4.97 out of 5 average rating, 90 reviews

Home in Davenport

LOOK! 8BR Super Nintendo Escape – 4469

A well-maintained exterior showcases a single-story house with a blue garage door and driveway, framed by a lush lawn and shaded trees. Inside, a bright living area is highlighted by modern decor and a large smart TV. A private screened pool is visible, surrounded by seating.