
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 $51 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!

No Airbnb Fees!Thematic Home/Pool/Game Room 218391
Unable to book this house? Don't worry! Check my profile for similar homes that might suit your needs WE HAVE 24/7 CUSTOMER SERVICE! Disney is 10 miles away! Beautiful single-family themed house with a fully equipped kitchen. Experience endless enjoyment with your loved ones in a private game room, complete with multiple arcades, a foosball table, and an air hockey table. Relax while having a BBQ with your family next to a private pool. Shopping malls, restaurants, and attractions are nearby.

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.

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.

Luxury Villa! /Game Room/ Pool Heater
Luxury Villa on a gated community in Kissimmee (Four Corners). Modern. Situated 10 min. from Disney theme parks. Well decorated and presented. Game Room, Mini Gym, Beautiful, large pool deck which is totally enclosed and secluded. There is a private Pool and overflow Spa. Three Bedrooms and Bedroom one is separate from the main house but still enclosed in the building. This would be ideal for a young couple within the group as it has its own bathroom, small kitchen and also total privacy.

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

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!

Disney Theme Rooms | Private Pool | Storey Lake
Welcome to your dream vacation at Storey Lake, one of the most loved resorts by travelers visiting Orlando. This beautifully designed 4-bedroom, 3-bath townhome was created to bring comfort, fun, and unforgettable memories all in one place, just minutes from Disney and the area’s top attractions.

Modern 5BR Home with Game Room and Pool at Windsor
Luxury 5BR themed home in Windsor Cay Resort featuring an immersive game room, stylish living spaces, and a private pool. Designed for families and groups seeking comfort, fun, and unforgettable stays just minutes from Orlando’s top attractions.
Popular amenities for Kissimmee family-friendly rentals
Family-friendly home rentals with a hot tub

Luxury 9BR Disney Home|FREE H Pool & Solara Resort

Magical Disney Family Escape with Pool & Game Room

Kissimmee, Heated Pool, Game Room. Luxury

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

Mickey Fantasia Family Friendly w/accessibility

Epic Game Room Villa Golf Course View Near Disney

*NEW* Space Odyssey: Pool, Spa, Cinema, Games+PS5

Clubhouse Birdie: Resort Home near Disney
Family- and pet-friendly home rentals

Villa Resort Club

Sleeps 23 | 9BR Home w/ Private Pool & Game Room

Harmony | Heated Pool | 10 min Universal & Epic.

Private Pool + Spa Game Room •4m Disney •Pinball

3 Bed Pool/Spa w/ Sunset Water in Margaritaville

*Hibiscus Hideaway* Minutes to Disney+Free Resort!

Amazing Villa near DisneyWorld FREE heated-pool

Luxury Encore Pool Spa Pets Game Rm Theater Gym
Family-friendly home rentals with a pool

7 Bd/ 7 Ba/ Solara Resort (2327 Sr)

Montego Bay Retreat | 15 Min to Disney

New and Unique Disney Airbnb!

SUPER Cozy & Fun Villa w/ Pool & BBQ | Near Disney

Mickey Disney Villa | Pool | Arcade | King Suites

Star Wars & Wizard Themed XL Pool Home Near Disney

12BR Luxury Disney Villa/Sleeps 29/Arcade/Pool

Brand New - 12br - Sleeps 34 - Theatre/Arcade/Pool
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $268 NZD | $282 NZD | $299 NZD | $306 NZD | $263 NZD | $272 NZD | $268 NZD | $236 NZD | $212 NZD | $223 NZD | $250 NZD | $299 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
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- Family-friendly rentals United States
- Walt Disney World Resort
- Orange County Convention Center
- SeaWorld Orlando
- Disney Springs
- Orlando / Kissimmee KOA
- Universal's Volcano Bay
- Epcot
- Camping World Stadium
- Kia Center
- Disney's Animal Kingdom Theme Park
- University of Central Florida
- Discovery Cove
- Tinker Field
- Old Town
- LEGOLAND Florida Resort
- Disney's Hollywood Studios
- ChampionsGate Golf Club
- ICON Park
- Aquatica
- Island H2O Live!
- Blue Spring State Park
- Kennedy Space Center
- Kissimmee Lakefront Park
- King's Landing







