
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 5,840 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 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
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! Home Theater! Pvt Pool/ Spa 278291
Unable to book this house? Don't worry! Feel free to check my profile for similar homes that might suit your needs WE HAVE 24/7 CUSTOMER SERVICE Disney is just a short 8-mile drive away Tired of visiting the parks every day? Step inside this beautiful thematic 2,169 sqft house with a private pool, spa, BBQ, Star Wars themed movie theater, and a Mario Kart game room complete with arcades, pool table and foosball table all designed for family enjoyment! Make your vacation truly unforgettable!

Rotating VR Machine, Arcade, Slide | 3mi to Disney
Tiki Hut over the Reef hosted by Whimsy Getaways website is a one-of-a-kind villa boasting a mind-blowing 9D 360° rotating VR Machine with thrilling rollercoaster rides! 2 incredible fully immersive game rooms provide endless entertainment, while 3 fully immersive themed bedrooms will spark your imagination. Subtle themed touches ensure adults enjoy the whimsy too! This spacious villa is the largest floor plan within 4 miles to Disney, is perfect for families seeking an unforgettable escape.

Magical Moments Luxury Disney Villa, Pool & Arcade
Magical Moments Villa Our 8 bedroom, 5 bathroom themed pool home offers luxurious and spacious living for families visiting the Orlando area theme parks - it's only a short, 12 mile drive away from Mickey and all his friends, located in the fabulous Champions Gate Resort. EIGHT themed bedrooms, including two impressive themed King Suites, six additional themed bedrooms, themed bathrooms, a themed home theater, themed game room, lanai & heated pool await the fun seeking members of your family!

Magical Disney House-Pool & Hot Tub,Free Waterpark
Also own the house across the street for renting two homes at same time. ask about that home. Ask about our early check in/out options Mickey Mouse & Star Wars bedrooms, gameroom, pool & hot tub with bbq, loungers,cozy couch and plenty of fun to be had under the sun or under the stars with outdoor lights over pool. 1st and 2nd floor master suites -great for two families. Our gated resort community at Solterra gives you access to FREE pool/lazy river/water slide/playground and much more

Cozy Themed Villa 6 BR | Close to Disney
🏖️☀️🏄♀️Stay just minutes from Disney in this spacious 6-bedroom home, perfect for a family getaway. It comfortably sleeps up to 14 guests and is designed for both kids and adults to enjoy. Located in Windsor Hills Resort — one of the closest communities to Disney World — you’ll have quick and easy access to the parks. Enjoy themed bedrooms, a game room, and your own private patio and pool — great for relaxing after a fun day at Disney.🌴👙🩳🥽🩴 ❤️❤️We'd love to welcome you here!

Family Fun in Near Disney Star Wars, Pool, BBQ
This beautifully designed townhouse is centrally located and will provide everything you need to create wonderful memories with your family. There is a free heated private pool and BBQ grill in the patio, large screen TVs, a fully stocked kitchen and Star Wars / Mickey theme rooms. The resort amenities include a pool with a tiki bar, pirate boats and a lazy river, as well as kids' playgrounds and a gym! This magical place is ideally located close to all the main parks and attractions!!

Free Waterpark, Fantasy World, The Mickey House
It is a beautifully decorated house located a few minutes from Disney, Universal Studios, Sea World, and other attractions. Close to restaurants, Walmart, Target, Publix, and other stores. It is a nice and fun resort, with free access to our gorgeous pool area, waterslides, lazy river, and sports courts. The pools and lazy river are heated and open all year long. Shuttle to major parks is available and must be paid separately at the front desk. Kids 3 years old and under ride free.

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 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.

Disney 5mi * NEW Themed Rooms! WALK to Clubhouse
This is where your family's best vacation story begins! ⭐️ Themed Bedrooms - Frozen ❄️ / Star Wars ⚔️ 🧚🏻 Magic Kingdom: 5 mi 🌌 Epic Universe: 18mi 🌏 Epcot: 9 mi 🎢 Universal Studios: 14 mi 🐋 SeaWorld: 10 mi 👷♂️ LEGOLAND: 29 mi ✈️ Orlando Airport (MCO): 25 mi 🤩 Free Clubhouse Amenities ♨️ Heated splash pool in back patio 🌭 BBQ grill 🧺 Washer/dryer on premises 🚗 2 parking spaces 🛜 High speed Wi-Fi 📺 Smart TV's w/ STREAMING in every room (BYO Passwords)

Top1% *La Piu Belle* Retreat at Storey Lake View
Welcome to **La Piu Belle Retreat** – a stylish, sunny, and serene escape at Storey Lake Resort. This 2-bedroom condo features boho-chic decor, a fully equipped kitchen, a bright balcony, and cozy vibes throughout. Enjoy access to a water park, gym, and more. Perfectly located just minutes from Disney, premium outlets, and top restaurants. Excellent Reviews: Our guests rave about their experiences, highlighting our cleanliness, location, and exceptional service.

Enchanted Home Near Disney • Arcade Room
Welcome to our enchanting 3-bedroom, 3-bathroom haven, meticulously designed to embrace your family's comfort and imagination! Step into themed suites straight out of your favorite stories, including Toy Story and Mickey Mouse. With a spacious capacity for up to 10 guests, your Disney adventure begins right here! The following extra services include additional costs: Grill Early Check-in Late Check-out
Popular amenities for Kissimmee family-friendly rentals
Family-friendly home rentals with a hot tub

Free Arcade! All Rooms Themed! South Facing Pool!

Epic Windsor Hills Poolside Escape

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

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

Your Dream Vacation—Disney Magic Brought to You!

"Disney Serenity": Luxe 8BR Villa/ Privacy/ Pool

Be Our Guest !

Resort Home 3.5 miles to Disney with home theater
Family- and pet-friendly home rentals

Cozy House with Private Pool. Kissimmee/Orlando

Luxury 5BR free heat private pool Disney Universal

Power Up Palace | Disney, River & Slides

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

Mad Men Magic Kingdom House*FAB POOL*OutdoorMOVIE

Gorgeous 5BR PetFriendly @Encore Near Disney 7693

Resort acess - Themed rooms

Magical Mickey Home | 8min->Disney!
Family-friendly home rentals with a pool

Arcade + Pool Villa • 2.5 Miles to Disney

4BR Disney & Universal Themed Villa Reunion Resort

10 min to Disney| Themed | Sauna | Pool | Golf Sim

Toy Story Villa | Arcade | Pool | Resort Access

Epic Home | Water Park | Disney | Pool

206 Lakeview Magic Stay – Mickey & Stitch Rooms

Near Disney/Private Pool/Steps to Resort Amenities

24/7 gated 6 /3.5 bath off 192,pool, tennis 1073
When is the best time to visit Kissimmee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $274 NZD | $287 NZD | $305 NZD | $270 NZD | $237 NZD | $258 NZD | $274 NZD | $241 NZD | $216 NZD | $227 NZD | $255 NZD | $305 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 |
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- Family-friendly rentals Osceola County
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- 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
- Camping World Stadium
- Magic Kingdom Park
- 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
- ICON Park
- Aquatica
- ChampionsGate Golf Club
- Tinker Field







