
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 5,830 holiday rentals in Kissimmee

Nightly prices starting at
Kissimmee holiday rentals start at $52 NZD per night before taxes and fees

Verified guest reviews
Over 251,460 verified reviews to help you choose

Pet-friendly accommodation
Find 1,020 rentals that welcome pets

Holiday rentals with a pool
5,450 properties feature pools

Rentals with dedicated workspaces
3,340 properties have a dedicated workspace

Wi-Fi availability
5,800 of Kissimmee holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi 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.

Top Floor, 3bd, FREE Clubhouse, Kids Room, Disney
*BRAND NEW CONDO* This penthouse vacation condo offers stunning pool views, accessible via an elevator, is ideally situated just moments away from Walt Disney World, restaurants and shops. Boasting 2 bedrooms, 1 KidsRoom and 2 bathrooms, it's the ultimate family retreat, ensuring a magical vacation. Inside, you'll find a dedicated Kids' Room and an exciting Arcade, while the kitchen adds to the fun with its unique features, including a Waffle bar and Popcorn corner for the whole family to enjoy!
4.97 out of 5 average rating, 122 reviews
WaterPark+Arcade+KingBed+Hot Tub+NearDisney
Family-Friendly Orlando Vacation Home Near Disney & Universal ✨ Welcome to your dream getaway! This spacious 4-bedroom, 3-bathroom villa is perfectly located just 25 minutes from top attractions. With themed bedrooms, first floor bedroom and bathroom and access to resort-style amenities, our home is designed for unforgettable family vacations.🌟 Why Guests Love It: •Themed Bedrooms: Lion King mu •Resort-Style Amenities: Relax in the tropical pool, hot tub, fitness center, clubhouse, and arcade.
4.94 out of 5 average rating, 142 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!
4.9 out of 5 average rating, 126 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!
4.99 out of 5 average rating, 158 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.
4.87 out of 5 average rating, 457 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.
5.0 out of 5 average rating, 143 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!
4.9 out of 5 average rating, 177 reviews
Apartment in Four Corners
Escape to this stylish 2-bedroom, 2-bathroom condo, perfect for families or friends seeking a memorable getaway. Enjoy spacious living area, complete with a comfortable sofa bed, and a fully-equipped kitchen. Relax in luxury with a king-size bed and en-suite bathroom. Access at NO ADDITIONAL cost to world-class pools, a lazy river, and a fitness center . Enjoy complimentary Wi-Fi and parking Located in the heart of Champions Gate, Aprox. 15 mins to Disney Parks & 30mins to Universal
4.9 out of 5 average rating, 108 reviews
Dream Vacation | Sleeps 18 | Themed Arcade & Rooms
Experience the magic of Disney World, Universal Studios, and the very best of Orlando from the comfort of this luxury private resort! Conveniently located in Storey Lake Resort, enjoy the the resort style amenities or explore the world class attractions in Orlando and Kissimmee. Minutes from Disney World, Universal Studios, Sea World, Premium Outlet Malls, and beyond! This modern property is focused on providing an unforgettable and exceptional family centric vacation experience!
4.99 out of 5 average rating, 134 reviews
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 :)
4.95 out of 5 average rating, 194 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.
4.99 out of 5 average rating, 255 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!
4.96 out of 5 average rating, 118 reviewsPopular amenities for Kissimmee family-friendly rentals
Family-friendly home rentals with a hot tub

6BR Family Fun Starts Here with Pool & Games 4354!
4.88 out of 5 average rating, 140 reviews
Minutes to Disney: Resort Home w/ Private Pool,
4.81 out of 5 average rating, 187 reviews
5BR Disney Pool Villa | Arcade + Spa | Sleeps 11
4.95 out of 5 average rating, 119 reviews
Mickey Fantasia Family Friendly w/accessibility
4.99 out of 5 average rating, 150 reviews
Mickey Pool • Frozen • Waterpark • Near Disney
4.96 out of 5 average rating, 220 reviews
Andy's Toy Chest at Resort Minutes from Disney!
4.94 out of 5 average rating, 248 reviews
Free Waterpark, Fantasy World, The Mickey House
4.83 out of 5 average rating, 137 reviews
Resort Home 3.5 miles to Disney with home theater
4.85 out of 5 average rating, 157 reviewsFamily- and pet-friendly home rentals

Disney 5BR • Private Pool Free Heat • Pet Friendly
4.96 out of 5 average rating, 175 reviews
8Bd 4K Movie Theater 155 Inch Screen Pool & Spa
4.85 out of 5 average rating, 142 reviews
4BRThemed/Pool/Near Disney/PetsOk/Free BBQ&Resort
4.95 out of 5 average rating, 104 reviews
Themed Illusion House •Waterfront •Private Pool
4.99 out of 5 average rating, 174 reviews
Amazing Friends 5BR+Private Pool+Lazy River
4.96 out of 5 average rating, 115 reviews
4BD Deluxe nxt to Mickey
4.85 out of 5 average rating, 178 reviews
*Plumeria Place* Minutes to Disney+Free Resort!
4.95 out of 5 average rating, 206 reviews
Pet-Friendly Disney Theme 4BR•Heated Pool•Game Rm
4.99 out of 5 average rating, 161 reviewsFamily-friendly home rentals with a pool

Magic Condo at a Resort Near Disney
4.97 out of 5 average rating, 199 reviews
WH Condo. Pool/Waterpark and close to Disney!
4.85 out of 5 average rating, 189 reviews
Disney Theme Rooms | Private Pool | Storey Lake
5.0 out of 5 average rating, 45 reviews
4BR Disney & Universal Themed Villa Reunion Resort
5.0 out of 5 average rating, 23 reviews
2026 Themed NEW 08 Bedrooms At Solara Resort
4.86 out of 5 average rating, 14 reviews
Amazing Themed 07 Bedrooms at Solara Resort
4.93 out of 5 average rating, 14 reviews
12BR Disney Luxury Retreat - Pool, Theater & Fun!
4.98 out of 5 average rating, 58 reviews
2319 7BD Beautiful Family Home with Private Cinema
4.89 out of 5 average rating, 55 reviewsWhen is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $276 NZD | $290 NZD | $307 NZD | $314 NZD | $271 NZD | $279 NZD | $276 NZD | $243 NZD | $218 NZD | $229 NZD | $257 NZD | $307 NZD |
| 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
- Miami Holiday rentals
- Four Corners Holiday rentals
- Miami Beach Holiday rentals
- Orlando Holiday rentals
- Fort Lauderdale Holiday rentals
- Tampa Holiday rentals
- Hollywood Holiday rentals
- Savannah Holiday rentals
- Jacksonville Holiday rentals
- Hilton Head Island Holiday rentals
- Key West Holiday rentals
- Cape Coral Holiday rentals
- Mansion rentals Kissimmee
- Luxury rentals Kissimmee
- Beachfront rentals Kissimmee
- Rentals with a sauna Kissimmee
- Lakehouse rentals Kissimmee
- Rentals with breakfast Kissimmee
- Resort rentals Kissimmee
- Cottage rentals Kissimmee
- Rentals with pools Kissimmee
- Waterfront rentals Kissimmee
- Townhouse rentals Kissimmee
- Villa rentals Kissimmee
- Beach house rentals Kissimmee
- Rentals with a hot tub Kissimmee
- Rentals with a kayak Kissimmee
- Apartment rentals Kissimmee
- Cabin rentals Kissimmee
- House rentals Kissimmee
- Ski-in/ski-out rentals Kissimmee
- Rentals with beach access Kissimmee
- Hotel rooms Kissimmee
- Pet-friendly rentals Kissimmee
- Serviced apartment rentals Kissimmee
- Tiny house rentals Kissimmee
- Holiday home rentals Kissimmee
- Private suite rentals Kissimmee
- Guesthouse rentals Kissimmee
- Condo rentals Kissimmee
- Rentals with an accessible height toilet Kissimmee
- Rentals with an accessible height bed Kissimmee
- Rentals with lake access 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
- Disney Springs
- SeaWorld Orlando
- Orange County Convention Center
- Orlando / Kissimmee KOA
- Epcot
- Universal's Volcano Bay
- Kia Center
- Camping World Stadium
- University of Central Florida
- Disney's Animal Kingdom Theme Park
- Tinker Field
- Discovery Cove
- Reunion Resort Golf Courses - Palmer & Watson
- Old Town
- LEGOLAND Florida Resort
- ChampionsGate Golf Club
- ICON Park
- Disney's Hollywood Studios
- Aquatica
- Southern Dunes Golf and Country Club
- Universal's Islands of Adventure







