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.

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Top Guest favourite

Villa in Osceola County

4.99 out of 5 average rating, 152 reviews

*Private Golf-Front Oasis with Pool, Spa & Cinema

Escape to one of Reunion Resort's most unforgettable homes, where luxury meets nonstop fun just minutes from Disney. Enjoy your private pool & spillover spa on the sprawling 2,000 sq ft pool deck, then take in golf course views from the separate fire pit terrace & balcony. Inside, discover a Star Wars theater/game room with digital pinball, arcade games & karaoke, a Marvel kids' suite with tube slide, Xbox Series S, and a hidden Harry Potter cupboard. Perfect for unforgettable family vacations.

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Guest favourite

Home in Kissimmee

4.9 out of 5 average rating, 125 reviews

Encanto at Emerald Island-Pool House by Disney

POOL HEATER OPTION!! Make some memories at this unique and family-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 aways from Disney's exit & parks!

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Top Guest favourite

A private patio area is presented, featuring a refreshing turquoise rug adorned with floral patterns. Two wicker chairs, accompanied by a small table and a potted plant, offer a cozy seating arrangement beside a sparkling pool, enclosed by a protective mesh screen.

Home in Kissimmee

4.95 out of 5 average rating, 113 reviews

Paradise Suite With Private Pool

Relax with the whole family at this peaceful place to stay. The spacious living area features windows that flood the space with natural light, while the kitchen is equipped with stainless steel appliances and granite countertops. The master bedroom offers a peaceful oasis with a spa-like master bath and walk-in closet. Property is located in a gated Golf community with a 3 mile walking trail that offers beautiful lake views. close to major intersections and shopping mall less than 2 miles

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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.

Condo in Osceola County

4.9 out of 5 average rating, 128 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)

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Top Guest favourite

Home in Kissimmee

4.97 out of 5 average rating, 186 reviews

Near Disney | Heated Pool, King Bed, Arcade

✨ Family-Friendly Retreat Near Disney in a gated, safe & quiet community 🏰 Loved by guests for its cleanliness, comfort, and fast communication. 🏊‍♂️ Unwind after park days in your private HEATED pool 🍔 Enjoy the outdoor BBQ for easy family meals 🎮 Have fun in the upgraded game room with pool table, ping pong, foosball, and a retro arcade ⭐ Hosted by 3 experienced Superhosts known for quick, reliable replies. A perfect balance of fun and relaxation. Book now as dates fill fast!

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Guest favourite

Aerial view of the pool area shows vibrant water slides winding through landscaped surroundings. Multiple swimming pools can be seen, complemented by palm trees and open spaces. Sun loungers are arranged around the pools, offering ample relaxation spots for guests.

Apartment in Kissimmee

4.9 out of 5 average rating, 108 reviews

Apartment in Four Corners

Escape to this stylish 2-bedroom, 2-bathroom condo, perfect for families or friends seeking a memorable getaway. Enjoy spacious living area, complete with a comfortable sofa bed, and a fully-equipped kitchen. Relax in luxury with a king-size bed and en-suite bathroom. Access at NO ADDITIONAL cost to world-class pools, a lazy river, and a fitness center . Enjoy complimentary Wi-Fi and parking Located in the heart of Champions Gate, Aprox. 15 mins to Disney Parks & 30mins to Universal

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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

4.97 out of 5 average rating, 1176 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.

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Top Guest favourite

A well-maintained exterior showcases a single-story house with a blue garage door and driveway, framed by a lush lawn and shaded trees. Inside, a bright living area is highlighted by modern decor and a large smart TV. A private screened pool is visible, surrounded by seating.

Home in Kissimmee

4.98 out of 5 average rating, 112 reviews

10 Minutes to Disney King Bed, Heated Pool, Arcade

✨ 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!

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Top Guest favourite

A unique sleeping area features a round bed designed to resemble a giant clam shell. Vibrant murals depicting underwater scenes adorn the walls, complementing the ocean-themed decor. Soft curtains in shades of green flow down from the ceiling, adding color to the tranquil space.

Home in Davenport

4.96 out of 5 average rating, 116 reviews

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!

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Top Guest favourite

Condo in Kissimmee

4.97 out of 5 average rating, 198 reviews

Magic Condo at a Resort Near Disney

Escape to paradise at this ultimate resort retreat! Enjoy a tiki bar, sparkling pools, tennis and basketball courts, a mini water park, and a kids' playground. Stay active at the full gym, play arcade games, or relax in the movie theater. Challenge friends to pool, ping pong, or unwind in the lounge area. Don’t forget to grab a keepsake from the souvenir store. Whether you're seeking adventure or relaxation, this resort has something for everyone!

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Superhost

Campervan/RV in Lake Wales

4.91 out of 5 average rating, 110 reviews

Cozy RV/Camper and Campsite.

WELCOME TO RANCHO Pura Vida ! "Where Memories are Made" Relax with the whole family at this peaceful place to stay. -ABOUT THE PROPERTY- This's a privately owned, Beautiful RV lot, fully equipped with everything you'll need for your stay. Bring nothing but the one's you love, food and drink. ¡ FREE GOLF CART INCLUDED ! For your convenience so that you can enjoy all the amenities that Westgate and River Ranch has to offer !

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Top Guest favourite

The collage showcases various areas of the lakeside home. Highlights include a private patio dining set, a resort-style pool, a comfortable living space with a dining table, and vibrant bedrooms featuring bunk beds and colorful decor. The picturesque lake view complements the outdoor spaces.

Townhouse in Kissimmee

4.99 out of 5 average rating, 188 reviews

Lake View - 5 Miles to Disney!

This family friendly lakeside home is just five miles from your favorite theme parks and surrounded by a multitude of dining options, retail shopping, grocery stores and entertainment right outside the resort. This smart home offers high-speed internet/wifi and endless entertainment is just a voice command away. This home is located within the popular gated Encantada resort (staffed by security personnel 24 hours a day).

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