
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.

"Castaway Oasis" 5 Bed Townhome, Heated Pool & BBQ
Welcome to“Castaway Oasis”,newly decorated luxury 5 bedroom 4.5 bath townhouse with private heated pool in the resort of Windsor at Westside. 3 KING Bedrooms,2 exciting Kids bedrooms, Lazy Boy Sleeper Couch in the Loft. The community is an upscale, gated resort with a 10,000 sqft Clubhouse, 2 Pools, Lazy River, Hot Tub, Kids Splash pool, Tiki Bar& Fireplace lounge, Fitness Center, Volleyball Court, Basketball Court, FREE Arcade. Complimentary access to all amenities is included for our guests.

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!

3 Epic Theme Rooms • Sleeps 19 • Pool/Spa • Disney
🏰 Your kids won’t just sleep here—they’ll have their own adventure! ✨ This home will create memories your family will never forget. Sleeps 19 near Disney! Enjoy 3 incredible themed bedrooms, including a Frozen Ice Princess Castle Room with slide, an Avatar Adventure Room, and a Toy Story Room. Spacious 7BR and 5.5 bath home with a private heated pool & spa, fully stocked kitchen, fast WiFi, Smart TVs, and plenty of space for large groups. Perfect for your next unforgettable Orlando vacation!

Mickey's Mansion Luxury Themed Pool Home, Arcade, Theater
Welcome to Mickey's Mansion, your magical vacation rental in the heart of Champions Gate! 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! Pool heat & the 1st tank of propane for the BBQ is included. Booking with us includes full access to the Champions Gate Clubhouse & Oasis Resort

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!

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

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.

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.

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.

Luxury 7BR Orlando Villa | Pool, Spa & Game Room
Experience the magic in this luxury villa just 10 mins from Disney! Enjoy themed kids' rooms (Moana, Harry Potter, Star Wars), a Donkey Konggame room, private pool & spa, and full access to Windsor at Westside’s resort amenities—lazy river, water park, arcade, and more. Perfect for families or groups looking for fun, comfort, and convenience in the heart of Orlando.

2026 Themed NEW 08 Bedrooms At Solara Resort
Our vacation homes will bring you to experience beyond a simple stay. You will be near the most famous themed parks in the world while feeling the comfort of your home, plus having the highest standard of luxury and modernity, with everything a vacation home in Orlando can offer you.

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

Themed Rooms, Pool, Theater & Arcade | Sleeps 22

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

Themed Disney Villa | Pool | Arcade | Resort ºoº

No Airbnb Fees! Pvt Pool & SPA / Game Room 272951!

Dream Vacation | Sleeps 18 | Themed Arcade & Rooms

New! Epic Dream House with Pool

Epic Game Room Villa Golf Course View Near Disney

5BR Mario& Princess Peach•Pool•Theater•Free Resort
Family- and pet-friendly home rentals

Villa Resort Club

Beautiful home. Private pool. Close to Disney!

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

Gorgeous 5BR PetFriendly @Encore Near Disney 7693

Epic Disney Villa • Hidden Arcade & Playroom!

4m Disney, Sun Trap, Mini Golf, Pool• Spa• Games

8Bd 4K Movie Theater 155 Inch Screen Pool & Spa

*Brand New!* Minutes to Disney + Free Resort!
Family-friendly home rentals with a pool

Montego Bay Retreat | 15 Min to Disney

New and Unique Disney Airbnb!

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

2640ST-Amazing home in the BEST resort near Disney

Your Dream Vacation—Disney Magic Brought to You!

Dazzling 9 BR+Brand New MARIO KART @ Champion Gate

New! Dickie's Dream Reunion

Brand New 9 Bedrooms Single Family Solara 87SA
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $277 NZD | $291 NZD | $308 NZD | $273 NZD | $240 NZD | $261 NZD | $277 NZD | $243 NZD | $219 NZD | $229 NZD | $257 NZD | $308 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 |
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 $53 NZD 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
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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
- Orange County Convention Center
- Universal Orlando Resort
- Disney Springs
- SeaWorld Orlando
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Camping World Stadium
- Epcot
- Universal's Volcano Bay
- Kia Center
- Disney's Animal Kingdom Theme Park
- Reunion Resort Golf Courses - Palmer & Watson
- Discovery Cove
- University of Central Florida
- Old Town
- ESPN Wide World of Sports
- LEGOLAND Florida Resort
- Disney's Hollywood Studios
- Aquatica
- ICON Park
- Tinker Field
- ChampionsGate Golf Club







