
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 $50 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, 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.

4BRThemed/Pool/Near Disney/PetsOk/Free BBQ&Resort
Discover luxury and convenience at our 4-bedroom townhome in Paradise Palms Resort. Enjoy a private pool, lakeview sunsets, and themed rooms featuring Moana, Avatar, Mario Bros, and Roblox. With two elegant king suites, world-class resort amenities, and only 9 miles from Walt Disney World, it's the perfect Orlando getaway. 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 a Disney Adventure! Learn More Below!

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!

New! Epic Dream House with Pool
Enjoy epic opening rates! Make some memories at this uniquefamily-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 away from Disney's exit & parks.

Magical 2 pool-Spa & Game Room Villa near “Disney”
Looking for stay away from the crowd but yet close to Disney ? This private pool themed home is perfect to complete your Dream Disney family vacation you always wanted. 15 miles /Magic kingdom -13 miles from Disney springs -15 miles from Epcot center -25 miles / 30 Universal Studios Make your stay Magical with our custom made themed rooms Star Wars play area and kitchen Romantic master Arabian night Avatar pandora Moana bedroom Just less than 2 miles from I4 hw

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)

10 Min to Disney | Kings | Heated Pool | Games
✨ Perfect family getaway just minutes from Disney magic! ✨ This spacious 4-bedroom home sleeps 9 and features 2 king beds, 4 full beds, and 1 twin, plus fun Mickey Mouse & Minion themed rooms kids love. Unwind in your private screened pool, enjoy the game room with arcade games, ping pong, foosball & pool table, or relax with cozy board-game nights. 🏰 Animal Kingdom 10 mins Epcot & Hollywood Studios 15 mins Book now and start making unforgettable family memories!

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.

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!

Montego Bay Retreat | 15 Min to Disney
Enjoy a stylish stay in this newly renovated 3-bedroom, 2-bath home, perfect for families and groups of up to 9 guests. Located only 15 minutes (8 miles) from Disney and close to Orlando’s top attractions, restaurants, and shopping. Relax in modern, comfortable spaces after a fun day at the parks. Outdoor grill available for $30/day (gas included). The perfect mix of location, comfort, and convenience for your Florida vacation! ✨

Lux Disney Villa | Pool, Theater/games | Sleeps 22
Epic 10-bedroom themed luxury villa near Disney — sleeps 22 — with private pool & hot tub, movie theater with reclining seats, and a Marvel/LEGO arcade featuring racing simulators, air hockey, foosball & pinball. Includes elegant king suites and magical kids’ rooms (Toy Story, Star Wars, Minions, Beauty & the Beast). Perfect for multi-family getaways — just 20 minutes from Magic Kingdom.

Remodeled 5BR | Pool, Theater & Themed Rooms
Welcome to a vacation home designed to make every day feel like part of the adventure. Beautifully remodeled and located inside the sought-after Solterra Resort, this spacious 5-bedroom, 5.5 bathroom retreat brings together contemporary comfort, playful themed spaces and resort-style fun, all within easy reach of Walt Disney World and Orlando’s most popular attractions.

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
Popular amenities for Kissimmee family-friendly rentals
Family-friendly home rentals with a hot tub

Mickey Fantasia Family Friendly w/accessibility

Windsor Orlando Private Arcades,Theater,Pool-Spa

Luxury Villa! /Game Room/ Pool Heater

Captivating home 12 minutes from Disney world Fl

No Airbnb Fees! Pvt Pool /Game Room/Resort! 274831

*Modern Luxury Reunion Oasis | Pool, Spa & Cinema

Lake View - 5 Miles to Disney!

Disney-Themed Home w/ Game Room & Private Hot Tub!
Family- and pet-friendly home rentals

OMG! Disney Area, Movie Theater, Game Room & Pool!

Villa Resort Club

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

1.4 miles to Disney Luxury resort home by Walmart

Apartment in Four Corners

Disney Encanto| Pool| BBQ & Backyard| free parking

Luxury Encore Pool Spa Pets Game Rm Theater Gym

Harmony | Heated Pool | 10 min Universal & Epic.
Family-friendly home rentals with a pool

Luxe Family Retreat | Pool Villa Near Disney & MCO

Baby Safe w *Indoor PlayGround*

New and Unique Disney Airbnb!

New! EPIC Playhouse- Theater, Bunks, Pool & Arcade

Private Villa | Pool | Game Room | Near Disney

7851 Luxury 5BR Home w/ Private Pool Near Disney

Star Wars & Wizard Themed XL Pool Home Near Disney

2640ST-Amazing home in the BEST resort near Disney
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $265 NZD | $279 NZD | $296 NZD | $302 NZD | $260 NZD | $269 NZD | $265 NZD | $233 NZD | $210 NZD | $220 NZD | $247 NZD | $296 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
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- Family-friendly rentals Osceola County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Walt Disney World Resort
- Universal Studios Florida
- Disney Springs
- SeaWorld Orlando
- Orange County Convention Center
- Universal Orlando Resort
- Orlando / Kissimmee KOA
- Universal's Volcano Bay
- Epcot
- Kia Center
- Camping World Stadium
- Disney's Animal Kingdom Theme Park
- University of Central Florida
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- Tinker Field
- Old Town
- LEGOLAND Florida Resort
- Disney's Hollywood Studios
- ESPN Wide World of Sports
- ChampionsGate Golf Club
- ICON Park
- Aquatica
- Southern Dunes Golf and Country Club







