
Family-friendly vacation rentals in Kissimmee
Find and book unique family-friendly homes on Airbnb
Quick stats about vacation rentals that are family-friendly in Kissimmee

Total vacation rentals
Explore 5,840 vacation rentals in Kissimmee

Nightly prices starting at
Kissimmee vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

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

Pet-friendly vacation rentals
Find 1,040 rentals that welcome pets

Vacation 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 vacation 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.

No Airbnb fee! Home with Game Room &Pvt Pool 29811
Unable to book this house? Don't worry! Check my profile for similar homes that might suit your needs WE HAVE A 24/7 CUSTOMER SERVICE! Take a breather from the parks! Step inside of this beautiful 5 bedrooms (2,270 sqft) house and discover a private pool, BBQ and a game room specially designed to entertain your family and keep the fun going. Enjoy the resort that offers a bar, pool, water slides, spa, lazy river, hot tub, kids splash pad, a game room, gym, sports court or rest on the hammocks!

"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.

Enchanted Villa with Lake View 6-Bedroom in Resort
In the exclusive Lake Berkley Resort, this magical manor is a spacious 6 bedroom, 3.5 bathroom home with private pool & spectacular lake views. A 10 minute drive to Disney World, 15 minutes to Sea World and 20 minutes to Universal’s Wizarding World of Harry Potter. Ensure an immersive experience at this thematic home, perfect for families & groups of friends looking to cook in the well stocked kitchen, enjoy meals together in Great Hall or patio by the pool and watch movies & more in the Common

Disney Retreat | Huge Pool with Spa | 2 King beds
Don’t leave that Disney Magic at the parks - experience it by coming home to your spacious 5 BR with 2 King suites, 3.5 baths, and newly renovated design. The high ceilings and open floor plan make it perfect for family time, while the private backyard oasis, complete with a pool and spa (heating optional) and Tiki Bar, offers a great space for relaxation. The themed bedrooms, including Star Wars, Frozen, and Mickey & Minnie, add a fun and whimsical touch that’s perfect for guests of all ages.

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.

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!

*Brand New*! Minutes to Disney! + Free Resort!
Closest FREE resort to Disney Parks! We've named it "Coral Cove" - a 6 bedroom 4 bathroom luxury villa that sleeps 14. Completely renovated in Dec 22! * Kitchen is loaded, & all baby gear provided. * Custom game room with A/C, LED panel lighting & ROCK CLIMBING WALL! *Outdoor space includes your own private pool, hot tub, overhead lighting, NEW BBQ grill & 10' custom-built farmhouse table to seat the whole family! *New Roku smart TVs & NEST tech! *Every detail has been thought of!

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

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.

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!

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.

The Magic Mansion 6BR Resort Pool Home Near Disney
Enjoy the magic of the highly sought after Magic Mansion, a fully Disney themed, six bedroom Orlando resort vacation home that sleeps 14 guests. Featuring a private pool, Avatar movie theater and arcade, themed rooms for the kids including Star Wars, Toy Story, and Alice in Wonderland themes, a Super Mario game room, and resort amenities INCLUDED Oasis Club and Retreat Club at Champions gate! Located only minutes from Disney World.
Popular amenities for Kissimmee family-friendly rentals
Family-friendly home rentals with a pool

Free Arcade! All Rooms Themed! South Facing Pool!

Lux Storey Lake Villa/Water Park/Pool/SPA/Themed

Near clubhouse new Storey Lake 15 guests pool&spa

9BD - Storey Lake - Newly Themed - Theatre, Games

2602SN - Stunning Home 5 Ensuites Near Disney

Luxe Disney Themed Home | Pool + Spa 8mi to Disney

Disney adventure resort style free waterpark 2633

Disney/Orlando Animal Kingdom Luxy Stay
Family-friendly home rentals with a hot tub

Magical Disney Family Escape with Pool & Game Room

Magical Hideaway - 15 min to Disney - Storey Lake

Modern Vacation Home Solara by Disney w/Pool& Spa

DISNEY 🎉 Game rm, heated Pool, Spa, Lazy rvr, BBQ

Resort Home 3.5 miles to Disney with home theater

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

5 Themed Rooms+GameRoom&Pool+Windsor Island Resort

12BR Disney Luxury Retreat - Pool, Theater & Fun!
Family-friendly home rentals with air conditioning

House located 10 minutes from the parks.

Disney Dreamer's Retreat

Best Location! Best Location!Villa in Kissimmee

Special Offer Pool,5bed,Game Room, Pet Friendly

Wizarding Wonders Await! 7BR, Private Pool, Games

Rapunzel's Magical Studio

Magical Stays Near Disney

Lakefront 9BR Resort Pool Home Near Disney World
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 580 | ﺩ.ﺇ 610 | ﺩ.ﺇ 646 | ﺩ.ﺇ 573 | ﺩ.ﺇ 503 | ﺩ.ﺇ 547 | ﺩ.ﺇ 580 | ﺩ.ﺇ 510 | ﺩ.ﺇ 459 | ﺩ.ﺇ 481 | ﺩ.ﺇ 540 | ﺩ.ﺇ 646 |
| 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 |
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- Family-friendly rentals Osceola County
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- Family-friendly rentals United States
- Universal Studios Florida
- Walt Disney World Resort
- Universal Orlando Resort
- Orange County Convention Center
- Disney Springs
- SeaWorld Orlando
- Universal's Volcano Bay
- Orlando / Kissimmee KOA
- Magic Kingdom Park
- Discovery Cove
- Epcot
- 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
- University of Central Florida
- Island H2O Live!
- Southern Dunes Golf and Country Club
- ChampionsGate Golf Club
- ESPN Wide World of Sports







