Family-friendly holiday rentals in Kissimmee

4.95 out of 5 average rating, 40 reviews

New! Epic Dream House with Pool

Enjoy epic opening rates! Make some memories at this uniquefamily-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 away from Disney's exit & parks.

5.0 out of 5 average rating, 138 reviews

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.

4.98 out of 5 average rating, 199 reviews

*Modern Luxury Reunion Oasis | Pool, Spa & Cinema

Wow-factor luxury meets unforgettable family fun, just minutes to Disney, at this show-stopping home in the exclusive Reunion Resort. Step outside to a massive 2,400-sq-ft southwest-facing pool deck with outdoor kitchen, private pool, overflow spa, and no rear neighbors—perfect for all-day sun and sunset swims. Inside: private movie theater, billiards game room, and spectacular Star Wars & Frozen II theme bedrooms with tube slide, plus Xbox and PlayStation for nonstop entertainment.

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.

4.98 out of 5 average rating, 110 reviews

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!

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, 254 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.

5.0 out of 5 average rating, 19 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.

A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.

4.96 out of 5 average rating, 114 reviews

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!

5.0 out of 5 average rating, 34 reviews

6BR Themed-Pool&Theater, Walk to StoreyLake Resort

✨ Create unforgettable memories at our renovated 6BR villa in Storey Lake Resort, just 6 miles from Walt Disney World 🎢! Relax by your private pool & spa 🏖️, enjoy a Star Wars theater 🎬, and themed bedrooms inspired by Inside Out, Harry Potter, Avatar, Mickey & Moana 🧙‍♂️🌊. Cook in a chef-ready kitchen 🍳, stay connected with fast WiFi ⚡, and explore resort pools, lazy river & gym 🌴. Family perks 👶 + free parking 🚗—your magical escape starts here!

5.0 out of 5 average rating, 5 reviews

10 Mi Disney 5BR Sleeps 18 Mario Arcade Pool

Disney closes. The vacation doesn’t. Your family playground is waiting when you get home. 🛏️ Room for the whole crew • Sleeps 18 👑 3 King bedrooms • 2 on main floor 🏰 Star Wars & Candy Kingdom bedrooms 🛝 Interactive kids loft with indoor slides 🏊 Private heated pool & spa ⭐ 5-minute walk to Storey Lake’s lazy river & clubhouse 🎢 Disney 10 miles • Universal 14 miles

New place to stay

Remodeled 5BR | Pool, Theater & Themed Rooms

Welcome to a vacation home designed to make every day feel like part of the adventure. Beautifully remodeled and located inside the sought-after Solterra Resort, this spacious 5-bedroom, 5.5 bathroom retreat brings together contemporary comfort, playful themed spaces and resort-style fun, all within easy reach of Walt Disney World and Orlando’s most popular attractions.

4.92 out of 5 average rating, 128 reviews

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

An arcade room is illuminated by vibrant wall murals featuring superhero and cartoon characters. An air hockey table occupies the center, with the blue walls creating a playful atmosphere. Neon accents give the space a lively feel, enhanced by overhead lighting.

4.95 out of 5 average rating, 115 reviews

Villa Near Parks | No Cleaning Fee | Pool & Arcade

• Near Disney • Near Universal • No Cleaning Fee • Hand-Painted Murals • Super Villa • Resort Amenities • Super Fast WiFi • Private Pool & Arcade • Corner Property • 2 King Beds • Stocked Kitchen • Comfortably Sleeps 11

Popular amenities for Kissimmee family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

4.96 out of 5 average rating, 165 reviews

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

4.99 out of 5 average rating, 136 reviews

Lux Disney Villa | Pool, Theater/games | Sleeps 22

A vibrant game room is showcased with neon accents and colorful lighting. Three black gaming chairs are positioned in front of a large screen, while a foosball table and a multi-game table are placed nearby. A netted structure adds a unique element to the playful environment.

4.88 out of 5 average rating, 121 reviews

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

4.97 out of 5 average rating, 143 reviews

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

An expansive backyard is featured, showcasing a striped hammock stretched between two posts. Lounge chairs are arranged nearby, with a swing set positioned to one side. The heated pool is enclosed within a screened area, providing a view of the clear, blue sky.

4.92 out of 5 average rating, 107 reviews

Kissimmee, Heated Pool, Game Room. Luxury

4.85 out of 5 average rating, 154 reviews

No Airbnb fees!Themed Home Pool/Spa/Gameroom 21811

A spacious themed room is depicted, featuring an imaginative design with a dark, cosmic ceiling. The room includes a large blue slide and a staircase, adjacent to cozy bean bag chairs for seating. Colorful space-themed murals enhance the playful atmosphere.

4.98 out of 5 average rating, 130 reviews

4mi to Disney | Games | Private Pool

4.99 out of 5 average rating, 149 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

Family- and pet-friendly home rentals

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.

4.87 out of 5 average rating, 455 reviews

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

4.95 out of 5 average rating, 112 reviews

Pool | Themes | Game Room

A private outdoor area features a pool with a spa, surrounded by a spacious deck. A basketball hoop is positioned nearby. A large inflatable swan floats in the water, while a hammock provides a cozy spot for relaxation. Lush greenery frames the scene under a colorful sky.

4.94 out of 5 average rating, 163 reviews

Luxury Encore Pool Spa Pets Game Rm Theater Gym

The themed bedroom features twin beds, designed to resemble spaceships, with bold, illuminated accents. A wall mural depicts a starry sky, while nearby, a gaming machine displays a classic arcade setup, creating an immersive atmosphere for guests.

4.95 out of 5 average rating, 109 reviews

Amazing Friends 5BR+Private Pool+Lazy River

4.85 out of 5 average rating, 314 reviews

Townhouse in Kissimmee

6 miles from Disney ! Private pool

Home in Buenaventura Lakes

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.

4.88 out of 5 average rating, 168 reviews

Villa Resort Club

4.92 out of 5 average rating, 133 reviews

A spacious outdoor seating area features a modern grey sofa set surrounded by lush green walls, with a ceiling fan above. The large pool area showcases palm trees and lounge chairs under a clear blue sky. The entertainment room includes vibrant murals and a slide, while the game area contains stylish bunk beds and a movie theater setup with colorful lighting.

Townhouse in Kissimmee

1.4 miles to Disney Luxury resort home by Walmart

An outdoor dining area features a large blue farmhouse table surrounded by matching turquoise chairs. The setting includes tableware arranged neatly, with the private pool visible in the background. A grill and greenery are also present, providing a relaxed atmosphere for outdoor meals.

4.92 out of 5 average rating, 166 reviews

*Coral Cove* Minutes to Disney+Free Resort!

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 21 reviews

Home in Clermont

5 Bd/ 5.5 Ba/ Windsor Cay (15839 Cc)

5.0 out of 5 average rating, 6 reviews

New and Unique Disney Airbnb!

A vibrant game room is filled with Mario-themed arcade machines featuring colorful graphics and interactive screens. Brightly colored carpet adds a playful touch, while a basketball game and other activities occupy the space. The walls are adorned with mural artwork inspired by popular video games.

4.93 out of 5 average rating, 94 reviews

Dazzling 9 BR+Brand New MARIO KART @ Champion Gate

New place to stay

Pool Movies|Game Room|Movie Theater|Private Lot

4.94 out of 5 average rating, 32 reviews

Luxury 7BR Orlando Villa | Pool, Spa & Game Room

A themed room featuring bright yellow and black décor inspired by popular characters. A large TV is mounted on a wall with playful eye designs above it. A life-sized figure of a Minion stands beside a colorful, circular rug, creating a fun environment for guests.

4.92 out of 5 average rating, 36 reviews

10 min to Disney| Themed | Sauna | Pool | Golf Sim

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.

4.92 out of 5 average rating, 59 reviews

House Resort at Encore Reunion - Disney