Family-friendly vacation rentals in Kissimmee

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

House for rent next to DISNEY Windsor at Westside features a grand 10,000 square foot resort clubhouse FREE FOR GUEST USE filled with amenities for active families that include multiple sports courts, children's playgrounds as well as a resort-style swimming pool and lazy river with splash water park. Tu Casa is an onsite restaurant and bar and there's even an ice cream shop to refresh yourself with some sweet treats. GAME ROOM- air hockey, basketball, themed rooms, billiards, designer bedrooms!

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!

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, 457 reviews

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.

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

Unable to book this house? Don't worry! Check my profile for similar homes that might suit your needs. WE HAVE A 24/7 CUSTOMER SERVICE! Escape the routine of visiting the parks every day and step inside of this brand-new house with 5 bedrooms, private pool, SPA, BBQ grill and a game room specially designed to entertain your family. You can also have some fun at the Clubhouse, which offers a bar/restaurant, a big pool with water slides, a lazy river, a spa, a gym, a playground, and mini golf.

5.0 out of 5 average rating, 143 reviews

Home in Davenport

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

Home in Davenport

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, 136 reviews

Storey Lake 10BR Villa Near Disney, Pool Waterpark

✨ Step into your own Disney adventure! Once an NBA star’s vacation home, this villa sleeps 23 and blends luxury with fun: • 🛏 Themed Bedrooms (Frozen, Cars, Harry Potter, Star Wars & more) • 🎬 Galactic Theater w/ 86” Screen, Surround Sound, Arcade, Xbox & Nintendo • 💦 Heated Pool & Spa w/ Lounge Seating + Peaceful Forest Views • 🎢 Resort Water Parks w/ Lazy River, Pirate Ship, Water Slides & Mini Golf • 📍 Prime Location: Only 7 Miles to Disney & 19 Miles to MCO attractions

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.

4.95 out of 5 average rating, 120 reviews

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 :)

Popular amenities for Kissimmee family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 150 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

4.92 out of 5 average rating, 131 reviews

Magical Disney Family Escape with Pool & Game Room

5.0 out of 5 average rating, 46 reviews

Disney Theme Rooms | Private Pool | Storey Lake

Superhost

4.87 out of 5 average rating, 15 reviews

2026 Themed NEW 08 Bedrooms At Solara Resort

5.0 out of 5 average rating, 23 reviews

4BR Disney & Universal Themed Villa Reunion Resort

4.97 out of 5 average rating, 101 reviews

12BR Disney Beach house 34 ppl Pool Theater Arcade

Superhost

4.85 out of 5 average rating, 62 reviews

Amazing Themed 05 BRD/Pool at Windsor Westside

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!

Family-friendly home rentals with air conditioning

5.0 out of 5 average rating, 72 reviews

Home in Osceola County

Your Dream Vacation—Disney Magic Brought to You!

Superhost

5.0 out of 5 average rating, 3 reviews

Themed Stay with PS5 + Poolside TV | W. Westside

A vibrant game room is highlighted by colorful Mario-themed wall art, featuring interactive gaming stations equipped with racing chairs. Adjacent, a home theater is presented with luxurious seating and a large screen, surrounded by atmospheric LED lighting. A resort-style pool and relaxing outdoor space are seen, complemented by poolside lounge chairs.

4.98 out of 5 average rating, 42 reviews

NEW Modern Villa Near Disney w/ Pool & Spa!

4.87 out of 5 average rating, 30 reviews

Mario Loft+Slide·Sleeps 26·Disney & Epic·Free Pool

4.89 out of 5 average rating, 62 reviews

The Disney House • Immersive Rooms • Gaming Lounge

4.95 out of 5 average rating, 21 reviews

Condo in Kissimmee

3121 Modern Condo Near Disney | Storey Lake Resort

4.98 out of 5 average rating, 45 reviews

Frozen/StarWars, FREE Waterpark, 10 min to Disney

5.0 out of 5 average rating, 24 reviews

Home in Clermont

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

Family-friendly home rentals with a hot tub

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!

4.9 out of 5 average rating, 127 reviews

Home in Davenport

PrivatePool•WaterPark•2 KingBeds•NearDisney•HotTub

4.95 out of 5 average rating, 104 reviews

4BRThemed/Pool/Near Disney/PetsOk/Free BBQ&Resort

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

4.97 out of 5 average rating, 123 reviews

Disney Pool Villa | Windsor Hills | Sleeps 8

4.94 out of 5 average rating, 249 reviews

Condo in Kissimmee

Andy's Toy Chest at Resort Minutes from 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

A private pool area is surrounded by a screened enclosure, featuring a jacuzzi spa and lounge chairs. The pool is inviting, with light blue water reflecting the sky's pink and purple hues. A serene lake is visible beyond the pool, adding to the tranquil setting.