Family-friendly holiday rentals in Kissimmee

4.97 out of 5 average rating, 225 reviews

A family-friendly living area is presented with a large, comfortable sectional sofa facing a flat-screen TV. Adjacent, a vibrant children's bedroom features a whimsical Moana theme with a sandy beach mural, complemented by a canopy bed adorned with tropical accents. The ceiling displays playful elements, enhancing the kid-friendly atmosphere.

Condo in Kissimmee

303_To Infinity & the Ocean Breeze Apartment

Welcome to your ultimate family getaway near Disney! This spacious 3-bedroom apartment is perfectly located just minutes from the magic of Disney. Designed with families in mind, it features two beautifully themed kids’ bedrooms—a Toy Story adventure and a Moana-inspired tropical escape—guaranteed to delight the little ones. Enjoy full access to an amazing waterpark, included free of charge, making every day feel like a vacation. Whether you're unwinding after a day at the parks or splashing th

4.9 out of 5 average rating, 126 reviews

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!

4.99 out of 5 average rating, 159 reviews

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!

4.87 out of 5 average rating, 457 reviews

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.

Villa in Kissimmee

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.

5.0 out of 5 average rating, 143 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.

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.

4.85 out of 5 average rating, 158 reviews

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!

4.9 out of 5 average rating, 177 reviews

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!

An aerial view highlights a vibrant pool area featuring a multi-loop waterslide. Surrounding the pools are shaded lounge chairs and umbrellas, with palm trees adding a tropical touch. The layout showcases a spacious lazy river and areas for relaxation.

4.83 out of 5 average rating, 137 reviews

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.

4.95 out of 5 average rating, 120 reviews

A themed bedroom features two uniquely designed sleeping areas, including a lower bunk and a spacious bed above. Vivid blue lighting enhances the space, while large windows dressed with sheer, dark curtains allow soft light to enter. A colorful wall art piece adds visual interest.

Villa in Kissimmee

Family Disney Villa | Pool + Arcade | 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!

4.95 out of 5 average rating, 194 reviews

A vibrant living area features a Super Mario-themed mural depicting iconic characters against a blue backdrop. Plush seating surrounds a coffee table styled with bright colors, while a playful rug showcases a character from the Mario universe, creating a fun and inviting atmosphere for relaxation and gaming.

Condo in Orlando

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 :)

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, 256 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.

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, 119 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!

Popular amenities for Kissimmee family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A collage showcasing various features of the property. The image highlights a themed bedroom with superhero decor, a private pool with a spa and BBQ grill, and a game room filled with colorful character designs. A water slide is also visible, inviting fun in the sun.

4.85 out of 5 average rating, 137 reviews

5BR Space to Gather with Pvt Pool/Spa & Games 4336

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.

4.99 out of 5 average rating, 190 reviews

Lake View - 5 Miles to Disney!

Aerial view of the resort showcases a large pool with lounge chairs and palm trees surrounding a tranquil pond. Colorful amenities, including slides, are visible, enhancing the outdoor recreational area.

4.99 out of 5 average rating, 123 reviews

Fabulous 2BR Home With Hot tub

4.97 out of 5 average rating, 123 reviews

Disney Pool Villa | Windsor Hills | Sleeps 8

4.92 out of 5 average rating, 131 reviews

Magical Disney Family Escape with Pool & Game Room

The image showcases a vibrant game room filled with arcade machines and billiards, accompanied by a resort-style pool featuring a lazy river and splash park. The private heated pool and spa are visible in the outdoor area, surrounded by palm trees and comfortable lounge seating.

4.95 out of 5 average rating, 241 reviews

DISNEY 🎉 Game rm, heated Pool, Spa, Lazy rvr, BBQ

4.95 out of 5 average rating, 187 reviews

Disney-Inspired Suites • Game Room • Summerville

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, 114 reviews

Kissimmee, Heated Pool, Game Room. Luxury

Family- and pet-friendly home rentals

A lush outdoor water complex showcases a winding lazy river surrounded by palm trees and landscaped greenery. Lounge chairs are positioned alongside the water, providing ample space for relaxation. In the background, a clubhouse and scenic waterfront can be seen under a bright blue sky.

4.96 out of 5 average rating, 176 reviews

Disney 5BR • Private Pool Free Heat • Pet Friendly

4.9 out of 5 average rating, 109 reviews

Aerial view of the pool area shows vibrant water slides winding through landscaped surroundings. Multiple swimming pools can be seen, complemented by palm trees and open spaces. Sun loungers are arranged around the pools, offering ample relaxation spots for guests.

Apartment in Kissimmee

Apartment in Four Corners

Superhost

A colorful bunk bed structure is featured, decorated in vibrant shades of yellow, blue, and orange. The mural backdrop depicts a jungle scene with a leopard and tropical plants, enhancing the playful atmosphere of the room. Spiral staircases offer access to the upper sleeping area.

Townhouse in Davenport

WaterPark+Arcade+KingBed+Hot Tub+NearDisney

4.94 out of 5 average rating, 143 reviews

4.85 out of 5 average rating, 142 reviews

Villa in Kissimmee

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

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.

4.88 out of 5 average rating, 110 reviews

EPIC 8BD Theme Villa, Sleeps 19, 15 min to Disney

4.88 out of 5 average rating, 130 reviews

4m Disney • Pool • Spa • Cinderella Theme, Games

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.

4.96 out of 5 average rating, 115 reviews

Amazing Friends 5BR+Private Pool+Lazy River

The image displays the Summerville Resort sign, highlighting its proximity to Disney. A comfortable bedroom is shown, featuring two spacious beds and colorful wall art. An inviting patio area with outdoor seating is visible, alongside a community pool surrounded by lounge chairs and palm trees.

4.86 out of 5 average rating, 125 reviews

Comfy Family Villa|5min->Disney!

Family-friendly home rentals with a pool

4.97 out of 5 average rating, 123 reviews

Aerial view of a resort-style pool area features winding lazy river and miniature golf course set amidst lush greenery and palm trees. Bright blue water complements the surrounding landscaping, with lounge chairs and umbrellas positioned for relaxation. A community building is visible in the background.

Condo in Kissimmee

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

5.0 out of 5 average rating, 46 reviews

Disney Theme Rooms | Private Pool | Storey Lake

5.0 out of 5 average rating, 23 reviews

4BR Disney & Universal Themed Villa Reunion Resort

Superhost

4.87 out of 5 average rating, 15 reviews

2026 Themed NEW 08 Bedrooms At Solara Resort

4.97 out of 5 average rating, 101 reviews

12BR Disney Beach house 34 ppl Pool Theater Arcade

4.98 out of 5 average rating, 58 reviews

A vibrant collage of themed spaces showcases the enchanting variety within the home. Featured are a luxurious bedroom with a grand bed, a playful winter-themed room, a themed home theater, and a pool area with a spa set against colorful lighting.

Home in Orlando

12BR Disney Luxury Retreat - Pool, Theater & Fun!

5.0 out of 5 average rating, 11 reviews

2026 NEW 7BR Pool Home Near Disney | Solara Resort