
Family-friendly holiday rentals in Kissimmee
Find and book unique family-friendly homes on Airbnb
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 $42 AUD per night before taxes and fees

Verified guest reviews
Over 241,480 verified reviews to help you choose

Pet-friendly accommodation
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

Wi-Fi availability
5,820 of Kissimmee holiday rentals include Wi-Fi 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
Top-rated family-friendly rentals in Kissimmee
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Magical Pool Villa-close to Disney Game/movie Room
The whole family will have fun in our Magical Disney Home where the Magic of Mickey Mouse,Toy Story, Frozen and Minion bedrooms with Sensor Songs when you walk in each room, uv and Led lights.Color changing Led lights in pool + bbq area, loungers for sun tanning.This Villa has Disney Hand UV light Painted by a local artist and a Game room with air hockey arcade, your children will feel the Magic as soon as they walk in the home, from smell to sound to sight This is it!Your Magical Dream Vacation

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!

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.

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!

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.

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)

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.

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.

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5
Stylish Design, Luxurious Comfort & Endless Entertainment, with a sprawling 2200 ft2 southwest facing pool deck & outdoor kitchen, no rear neighbors on a beautiful forest in the stunning 3.5 square mile Reunion Resort. You will have your own private pool with overflow spa, movie room, billiards - game room, 4 theme rooms: OUTER SPACE, MARVEL SUPERHEROES with a TUBE SLIDE, FROZEN II, HARRY POTTER CUPBOARD, PS5, within minutes to Disney.

Fully Themed | Pool | SPA | Game Room | Water Park
Welcome to your private resort escape at Windsor Island Resort! This beautifully designed villa offers the perfect blend of comfort, space, and resort-style fun — ideal for large families and group getaways. Located in a prime gated community just minutes from Orlando’s top attractions, this home is designed to help you relax, reconnect, and make unforgettable memories.

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

Cozy family home w/ heated pool 15 min. to Disney
Modern family home in a gated community (very quiet neighborhood). 2391 sq ft with 5 bedrooms, 4.5 bathrooms, heated pool*, BBQ*, gaming room, 60'' Full HD TV, free unlimited high-speed wi-fi, central AC/Heating. 15 minutes driving to Disney.
Popular amenities for Kissimmee family-friendly rentals
Family-friendly home rentals with a hot tub

Disney Orlando vacation home with private pool 2

Disney Retreat | Huge Pool with Spa | 2 King beds

Lakeside Paradise, 15 min Disney + Saltwater Pool

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

Mickey Fantasia Family Friendly w/accessibility

Game & Theater Room, Castle Bunks, Pool & Spa

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

4m Disney Sun, Free Snacks, Golf, Pool• Spa• Games
Family- and pet-friendly home rentals

Villa Resort Club

Beautiful home. Private pool. Close to Disney!

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

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

🏰 Disney Princess Crownhouse! Closest to Disney!

Amazing Villa near DisneyWorld FREE heated-pool

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

Disney Themed home with Private Pool & Lazy River!
Family-friendly home rentals with a pool

House located 10 minutes from the parks.

7BD Villa w/ Pool, Spa & Game Room

Breathtaking 4BD w/ Free Resort Amenities!

10BR Theater Pool Little Mermaid Alice 16295

Luxury Home w/ Pool & 6 Beds near Disney

New! Eights Mansion Themed House w/pool by Disney

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

New 5BR Home w/ Pool, Game Room & Themed Rooms
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $210 AUD | $213 AUD | $224 AUD | $218 AUD | $192 AUD | $208 AUD | $221 AUD | $194 AUD | $175 AUD | $183 AUD | $206 AUD | $246 AUD |
| Avg. temp | 16°C | 18°C | 20°C | 22°C | 25°C | 27°C | 28°C | 28°C | 27°C | 24°C | 20°C | 17°C |
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Four Corners Holiday rentals
- Key West Holiday rentals
- Tampa Bay Holiday rentals
- Resort rentals Kissimmee
- Rentals with an accessible height bed Kissimmee
- Cottage rentals Kissimmee
- Villa rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Rentals with pools Kissimmee
- Lakehouse rentals Kissimmee
- Rentals with a kayak Kissimmee
- Beachfront rentals Kissimmee
- Apartment rentals Kissimmee
- Mansion rentals Kissimmee
- Rentals with breakfast Kissimmee
- Beach house rentals Kissimmee
- Rentals with a hot tub Kissimmee
- House rentals Kissimmee
- Fitness-friendly rentals Kissimmee
- Rentals with a sauna Kissimmee
- Rentals with lake access Kissimmee
- Rentals with a fire pit Kissimmee
- Townhouse rentals Kissimmee
- Condo rentals Kissimmee
- Holiday home rentals Kissimmee
- Cabin rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Rentals with beach access Kissimmee
- Rentals with an EV charger Kissimmee
- Private suite rentals Kissimmee
- Guesthouse rentals Kissimmee
- Rentals with a fireplace Kissimmee
- Rentals with a patio Kissimmee
- Smoking-friendly rentals Kissimmee
- Rentals with a washing machine and dryer Kissimmee
- Pet-friendly rentals Kissimmee
- Waterfront rentals Kissimmee
- Rentals with an accessible height toilet Kissimmee
- Tiny house rentals Kissimmee
- Hotel rooms Kissimmee
- Rentals with a home theatre Kissimmee
- Rentals with outdoor seating Kissimmee
- Family-friendly rentals Osceola County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Walt Disney World Resort
- Universal Studios Florida
- Universal Orlando Resort
- Walt Disney World Resort Golf
- Orange County Convention Center
- Disney Springs
- Magic Kingdom Park
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Discovery Cove
- Epcot
- ESPN Wide World of Sports
- Disney's Animal Kingdom Theme Park
- Kia Center
- Old Town
- Reunion Resort Golf Courses - Palmer & Watson
- Camping World Stadium
- Aquatica
- Disney's Hollywood Studios
- ICON Park
- Island H2O Live!
- Southern Dunes Golf and Country Club
- University of Central Florida






