Family-friendly holiday rentals in Osceola County

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Osceola County

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1

Top guest favourite

Townhouse in Davenport

4.97 out of 5 average rating, 115 reviews

No Airbnb Fees! Pvt Pool/ Game Room/Resort 276301!

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! Tired of visiting the parks every day? Step inside of this beautiful 2,270 sqft house and discover a private BBQ, pool and game room specially designed to entertain your family and keep the fun going. Enjoy the resort's clubhouse with a restaurant, pool with water slide, spa, lazy river, gym, playground and a tennis court. Experience the vacation of a lifetime!

Top guest favourite

The modern living area features a spacious gray sectional sofa accented by colorful cushions. A minimalist coffee table is positioned centrally, and large sliding glass doors provide a view of the outdoor space, allowing natural light to fill the room. Light-colored cabinetry and appliances are visible in the kitchen area.

Apartment in Kissimmee

4.93 out of 5 average rating, 213 reviews

3150-303 Resort Pool View Disney Universal Orlando

Minutes from Disney World Orlando Florida, Modern & Stylish 2bed/2bath fully equipped apartment for up to 6 guests, located in the family friendly Storey Lake Resort. FREE Clubhouse & WATERPARK amenities: Heated Pool, Hot Tub, Kids Splash Zone, Water Slides, Lazy River, Gym, Tiki Bar, Ice Cream Shop & more. The apt is located: 10 min drive to DISNEY, 25 min to UNIVERSAL STUDIOS, 18 min to SEA WORLD. FREE Parking. FREE Waterpark. No extra FEES. Gated Resort with Security 24/7 & Self check-in!

Top guest favourite

A themed game room showcases a Batman-inspired design with a bright yellow slide leading to a two-level play area. An air hockey table is positioned prominently, surrounded by stylized dark walls, creating an immersive gaming environment.

Villa in Kissimmee

4.99 out of 5 average rating, 135 reviews

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!

Top guest favourite

A welcoming seating area is presented with a modern grey sofa adorned with red and black decorative pillows. Colorful framed vintage Disney posters decorate the walls, adding a playful touch to the space. A sign in the foreground highlights the absence of Airbnb fees.

Townhouse in Kissimmee

4.97 out of 5 average rating, 401 reviews

Waterpark, Batting Cage, Mini Golf | Near Disney!

**Waterpark closed for maintenance from January 5th to February 5th, 2026** (See photo 7 in album for details) Located just minutes from Disney World & steps from restaurants. Your reservation will give you access to the resort’s amenities for up to 6 people without an additional charge! ✪AMENITIES✪ FantasyWorld amenities include: -Lazy river -Water slides -Heated pools -Pool bar -Splash pad -Jacuzzi -Gym -Picnic & BBQ areas -Playground -Arcade -Batting cage -Sports courts -Mini golf & more

Top guest favourite

A private pool features a spacious deck and a whimsical swan float. Adjacent is a covered dining area with views of landscaped grounds. Inside, a kids’ tube slide and superhero-themed decor are seen, along with a game area featuring a billiards table and arcade console.

Villa in Osceola County

4.99 out of 5 average rating, 131 reviews

*Private Resort Oasis: Golf-Front, Pool/Spa/Cinema

The perfect balance of STYLISH DESIGN, LUXURIOUS COMFORT, & ENDLESS ENTERTAINMENT, beautifully situated with stunning views in the sprawling 3.5 square mile Reunion Resort. You will have your own private pool, spillover spa, STAR WARS cinema-game room with pinball, classic arcade games, and karaoke, MARVEL kids room with tube slide and double bunks, the latest Xbox Series S, a sprawling 2000 ft2 pool deck, fire pit, and even a HARRY POTTER cupboard hidden under the stairs, minutes to Disney.

Top guest favourite

Townhouse in Four Corners

4.96 out of 5 average rating, 169 reviews

Near Disney/Kid-Friendly/Disney-Themed/Water Park

Your magical vacation starts here! Just 15 minutes from Disney World, this beautiful, family-friendly home offers luxury, themed rooms, and fun, perfect for creating unforgettable memories. The home is located in the ChampionsGate area. It has 3 bedrooms, 2.5 bathrooms, modern furniture, and super fast internet. You will have free access to the Enclaves at Festival amenities center which features a large beach-entry pool, kids water park, beach volleyball, mini-golf, restaurant, and gym.

Guest favourite

An aerial view showcases a large pool surrounded by lounge chairs and palm trees. The pool area is defined by well-maintained landscaping, with a hot tub and a nearby shaded structure visible in the background, creating an inviting atmosphere.

Apartment in Osceola County

4.89 out of 5 average rating, 108 reviews

Stunning Orlando Condo 3 BR/2 bath, pets OK

This resort community is amazing to drive around in, let alone stay in. Just 20 to 25 minutes away from Disney World and Universal Studios and everything Orlando has to offer. Convenience stores (7-11), Dunkin' Donuts, CVS pharmacy, restaurants and grocery stores within walking distance. Three gorgeous pools and hot tub Jacuzzis, and world-class gym in the resort in this gated community with security. 5 minute drive to Champions Gate and I-4 highway. Up to 2 dogs/cats ($25/day/animal)

Guest favourite

The image displays a colorful two-story home with light green siding, accented by blue shutters. The pool area features a vibrant water slide and colorful play structures. The interior includes a children's sleeping area with themed decor and twin beds, creating a fun, inviting atmosphere.

Townhouse in Kissimmee

4.93 out of 5 average rating, 120 reviews

Brand New Margaritaville Key Lime House by Disney

Close to Disney! Stunning *New 3 bedroom/ 3 bath home located inside the Luxury community of Margaritaville. This private oasis is centrally Located, few minutes away from the parks and restaurants. Sunset Walk is located next to the resort and it has more shopping, restaurants, Dine-in Lux Theater, & entertainment, including "Estefan Kitchen" by Gloria Estefan. While you unwind & relax, kids will love the new spectacular waterpark, Island H2O Live. Welcome to your island adventure!

Top guest favourite

The outdoor living space features a cozy seating area surrounding a fire pit and a large dining table. A private swimming pool is illuminated in blue, with sun loungers lining the edge. The backyard is framed by palm trees, creating a tropical ambiance at dusk.

Villa in Kissimmee

5 out of 5 average rating, 111 reviews

8 BR Villa, Private Pool, Theater, Min to Disney!

Big and Beautiful Themed Vacation Villa in premium gated Encore Resort. Spacious main floor for entertaining large groups - bring the family and friends! Enjoy the included resort amenities a minute's walk from the front door. Or, relax around your private pool and custom summer kitchen. Enjoy big-screen movies and sound in the theater in premium loungers, and play classic arcade games! min from Disney, one of the closest villa resorts. Tons of shopping and dining nearby!

Top guest favourite

A treehouse is illuminated by warm string lights, nestled among large branches under a deep blue sky. The structure features large windows allowing views of the surrounding greenery, with a cozy seating area visible inside. A wooden walkway leads to the entrance.

Treehouse in St. Cloud

4.96 out of 5 average rating, 1,052 reviews

TreeHouse in the Cloud, (Close toTheme Parks

The treehouse is a private getaway for a couple that want to experience the magic. Check out video tours on U-Tube. Type in Treehouse in the Cloud. There have been several movie and other photo shoots done on property. Please text request and details, and we can negotiate fees. Our other AirBnB is just next door; Country gem horses close to Theme parks [link] Which is 1,000 sq ft and sleeps six.

Guest favourite

Townhouse in Kissimmee

4.88 out of 5 average rating, 113 reviews

Kid-Approved Stay – Pool, Parks & Themed Rooms!

Give your family a stay they’ll never forget! Kids can rule their own Frozen kingdom or battle in a galaxy far, far away, while adults unwind after action-packed park days. ✔ Themed kids’ rooms – Frozen castle & intergalactic escape ✔ Private splash pool for a refreshing break ✔ Spacious & modern layout for families & groups ✔ Prime location near Disney, dining & top attractions Don’t miss out—book Let It Go Galaxy before it’s gone!

Top guest favourite

The image displays a resort landscape featuring various pastel-colored buildings surrounding a large pool area. A view of the tranquil lake is visible, with numerous palm trees and lounge chairs positioned near the water. The highlighted apartment is located on the second floor of one building.

Apartment in Kissimmee

4.97 out of 5 average rating, 396 reviews

Gorgeous❤️ Pool & Lake View Condo near Disney Parks

Welcome to Runaway Beach Club — your peaceful escape just minutes from the magic! With airy high ceilings and Key West-style decor, you’ll feel at home the moment you walk in. Whether you’re visiting theme parks or just want to relax, this cozy retreat is tucked away from the chaos but close to everything. Perfect for couples, small families, or business travelers. Book your stay and unwind in your own private slice of paradise!