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Family-friendly holiday rentals in Kissimmee

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Kissimmee

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite
Home in Kissimmee
4.77 out of 5 average rating, 147 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!

Top guest favourite
Home in Kissimmee
4.97 out of 5 average rating, 120 reviews

Kids Love It More Than Disney! Pool + Games

Happy 2026 from Kissimmee! Westside Villa has just a few openings - snag it while you can! -20 minute drive to all Disney Parks -Private, heated pool; gas grill; EV charge on-site -Modern arcade: racing simulators, virtual reality, vintage games -3 king size suites with smart TVs; dedicated work space -2 pack-n-plays, highchair, strollers, wagon -Resort access: lazy river, splash pad, tiki bar, fitness center Arriving early in the day or leaving late? Ask about our half day add-on, if our cal

Top guest favourite
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.
Villa in Kissimmee
4.99 out of 5 average rating, 157 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!

Superhost
Home in Kissimmee
5 out of 5 average rating, 4 reviews

Aurora Lux| Heated Pool| Games Room| Mini Golf|BBQ

Welcome to Aurora Lux Villa, a luxury home in Kissimmee! - Pool - 15 mins to Orlando Airport - 25 mins to Epic Universe - 25 mins to Volcano Bay - 25 mins to Disney Springs - Outdoor Playground for kids & Climbing Dome - Mini Golf - BBQ, Fire Pit & Outside furniture - 12 PPL (2 KING, 1 QUEEN, 2 TWIN & 2 SOFA BEDS) - Washer & Dryer - Kids friendly & Travel Crib - Private Patio & Terrace - WIFI - Fully equipped kitchen - Free parking - Safe neighborhood - Self-check in - Hosts available 24/7

Top guest favourite
Home in Davenport
5 out of 5 average rating, 132 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.

Guest favourite
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.
Villa in Kissimmee
4.88 out of 5 average rating, 249 reviews

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

AMAZING Pool Deck Extension cira 2023! Its the BIGGEST pool deck at the resort! Plus JAW DROPPING, Fancy, Fun, Fountain Jets w/ LED lighting, high-end glass tile & a Mickey Mosaic giving you an ULTIMATE luxury pool experience. This SALT WATER POOL/SPA will leave your skin feeling soft w/ no eye-sting & it has botanical qualities for your muscles after long days at the parks! Enjoy all this plus our unique OUTDOOR MOVIE EXPERIENCE & FIRE-PIT for the BEST vacay ever only 6 miles to Disney!

Guest favourite
A whimsical children's bedroom features a castle-themed bed with a slide and light blue walls. The room is adorned with soft carpeting and a chandelier, providing ample space for play. Two doors lead to additional areas, completing the enchanting atmosphere.
Home in Kissimmee
4.88 out of 5 average rating, 58 reviews

Baby Safe w *Indoor PlayGround*

**Property Requires refundable Security Deposit**Close to Disney Parks! Home equipped for baby! Full nursery, double stroller, highchair, packnplay, outlet covers, baby gates, toys, books, bouncy, and more. Kids love the Toy Story indoor playground with ball-pit, trampoline & slide, the fun doesn't stop at Disney! 6 themed bedrooms (3 Kids & 3 Adult themes), 5 baths, appliance stocked kitchen, a movie/game loft w/ 2 queen sofa sleepers, in-ground pool and Jacuzzi with BABY GATE!

Top guest favourite
Home in Osceola County
5 out of 5 average rating, 64 reviews

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!

Top guest favourite
Home in Kissimmee
5 out of 5 average rating, 11 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.

Top guest favourite
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.
Home in Davenport
4.95 out of 5 average rating, 104 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!

Top guest favourite
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
4.99 out of 5 average rating, 142 reviews

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.

Guest favourite
A spacious water park area is showcased, featuring a pair of large water slides in green and blue spiraling down into a clear pool. Palm trees are visible in the background, with seating areas and safety features surrounding the pool.
Home in Kissimmee
4.95 out of 5 average rating, 118 reviews

Private Pool/Grill-Free Water Park-15Min to Disney

We have made sure that you and your family have the best nights and the greatest times during the day, where distances will not be a problem since the house is located near the most emblematic sites to visit in Orlando Florida, 17 minutes from Disney, 23 minutes from Universal, the house features a private pool and barbecue grill, Unlimited parking, and a gorgeous clubhouse.

Popular amenities for Kissimmee family-friendly rentals

When is the best time to visit Kissimmee?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$203 SGD$213 SGD$226 SGD$200 SGD$176 SGD$191 SGD$203 SGD$178 SGD$160 SGD$168 SGD$189 SGD$226 SGD
Avg. temp16°C18°C20°C22°C25°C27°C28°C28°C27°C24°C20°C17°C

Quick stats about holiday rentals that are family-friendly in Kissimmee

  • Total holiday rentals

    Explore 5,840 holiday rentals in Kissimmee

  • Nightly prices starting at

    Kissimmee holiday rentals start at $38 SGD per night before taxes and fees

  • Verified guest reviews

    Over 241,480 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 1,040 rentals that welcome pets

  • Holiday rentals with a pool

    5,500 properties feature pools

  • Rentals with dedicated workspaces

    3,330 properties have a dedicated workspace

  • Wifi availability

    5,820 of Kissimmee holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Kissimmee rentals

  • 4.7 Average rating

    Kissimmee stays receive an average rating of 4.7 out of 5 from guests

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