The 8 best family-friendly Airbnbs in Osceola County

A mansion beyond your wildest dreams? We’ve found it. You won’t believe what this Airbnb has in store – you may even need to click the link below for photo evidence. Ready to hear what lies within? Get this: a treehouse playroom with a slide and climbing wall, a bowling alley with arcade games, a home theater with 15 reclining chairs, a games room with an Xbox and shuffleboard, a fully-equipped fitness room and themed bedrooms for fans of superheroes and princesses. Oh, and a pool, of course. There’s something here for the whole family, and it’s safe to say the kids will be over the moon with your choice of accommodation. The common areas are uber-modern, with luxurious furnishings, dynamic light fixtures and marble floors. The adult bedrooms will make you feel like you’re sleeping in a hotel with their slick designs and huge beds. As if that wasn’t enough to keep you entertained, you’re also granted access to the amenities at Solterra Resort, which include a lazy river, tennis courts and playground. 

Rooms? 11 bedrooms. Sleeps 16+ guests. 
Location perks? A 25-minute drive from the Disney parks, Universal Studios and SeaWorld. You’re also 10 minutes away from Target and Publix! 
Time Out tip: We suggest paying the extra fee to use the patio grill – who doesn’t love a BBQ?

Vacations with the kids can be a little chaotic, but at least with this Airbnb, you’ve got a lake to look out onto when you need a moment’s peace. Keep an eye on the little ones as they splash around in the heated pool, all while taking some time for yourself on the sun beds set against a natural landscape of tranquil water and lush greenery. Extend your period of relaxation with a quality night’s sleep in the king bed – and as for the kids’ all-important sleeping arrangements, there’s a Mickey Mouse-themed room with two double beds (and a TV), making it suitable for older children too. Everything about this home is bright, welcoming and functional; the kitchen is full-sized and comes with a number of baby products from plates to a bottle sterilizer. A coffee maker and dishwasher are also available to lend a helping hand. The washer and dryer may come in useful if you’ve got a messy brood and there are extra toys in storage if they’re not distracted enough already. The BBQ grill is on standby when the weather permits, and the nearby playground is ready to tire out the tots if you’re not already headed to the famed theme parks.

Rooms? 3 bedrooms. Sleeps 8 guests. 
Location perks? Just minutes from the Disney parks with 3 parking spots available on-site. 
Time Out tip: Heating the pool costs an extra $35 per day and takes 48 hours to take full effect – recommended between the months of October and April.

This lavishly large townhouse sits within the idyllic gated community of Lake Berkley Resort. There’s plenty of space to spread out and have some time away from the rest of the family – whenever that may be necessary – and cozy social areas to bring the gang back together. The TV corner has a big L-shaped couch for lounging without limits and overlooks the pool out back, making it the perfect place to relax after a swim. The big window and glass doors bring in plenty of light, stretching across the whole open-plan living area. The kitchen layout allows for an inclusive environment where you can also keep watch of the kids as they play outside. The games room is a big perk for competitive families, with a well-kept pool table and foosball table. Though the kitchen is outfitted with enough appliances to take on any degree of meal prep, there’s a BBQ area with a picnic table by the walking trail if you fancy something grilled and need a change of scenery. A playground and beach volleyball court can also be found on the resort premises, along with a pond for fishing and nature trails.   

Rooms? 4 bedrooms. Sleeps 8 guests. 
Location perks? Close to Disney’s Magic Kingdom in the heart of Kissimmee, just off 192 highway. 24-hour manned gate to make guests feel extra safe and protect the secluded feel of the surrounding woodland and lakeside setting. 
Time Out tip: Make the most of the resort’s clubhouse, with a communal pool, Jacuzzi, cabana and gym facilities.

Bring the whole family (including the pets!) to this room-for-all grand home set on a peaceful golf course in the premier Reunion Resort. Soak up the quiet of your surroundings – before the kids wake up – from the sizeable second-floor porch overlooking the leafy pool area. The interiors are leveled up with statement furniture, glass details, and chandeliers, achieving a classic look that makes the oversized space still feel cozy and welcoming. This place was made for larger families, with four bedrooms, 6 TVs, and a fully equipped kitchen with a double-door fridge freezer. You can dine outdoors on the covered patio by the pool – or lay out snacks for when the kiddos decide to finally get out of the water. Need a tanning session? That can be arranged thanks to the comfy loungers placed directly in the sun. There’s even a Jacuzzi for the adults to spend some quality time in with a glass of wine. 

Rooms? 4 bedrooms. Sleeps 11 guests. 
Location perks? A private residence on a private golf course with natural settings for dog walking and biking. 10 minutes from Disney World. 
Time Out tip: There’s an outdoor bathroom and shower by the pool area to prevent that chlorine smell from being brought into the house. 

Styled to suit the average modern family’s taste, this trendy apartment provides a modest stay for those who like to keep active on vacation; the community's guest-access areas include a pool, gym, playground, and tennis court. The newly renovated space flaunts high-end finishes throughout and amenities to get excited about, from a PlayStation 5 to the communal sauna and property-wide air conditioning. We’re sure the laundry area will be a welcomed convenience, and the blackout curtains in the bedrooms will ensure everyone gets a restful night. Board games are available for families who bond best when there’s some friendly competition involved. There are also TVs in both bedrooms as well as the living room, giving guests the option to relax on their own or all together. 

Rooms? 2 bedrooms. Sleeps 6 guests. 
Location perks? Close proximity to a ton of attractions: 7 miles from Walt Disney World, 12 miles from Universal Studios, less than 6 miles from Gatorland, and near to a number of local outlet malls. 
Time Out tip: Head to Kissimmee’s Old Town Entertainment District to explore over 70 shops and restaurants.

Looking for a Kissimmee rental that’s not too big, easy to keep clean, and pretty cheap? Well this place meets all your criteria and more – and when we say ‘more’, we mean a mini waterpark out back. Get the kids even more excited for this year’s family vacation by booking this accommodation that’s all about convenience. Look out for your future self – who you just know won’t want to spend their downtime cleaning – with this easy-to-maintain apartment that’s uncluttered, compact, and almost exclusively made up of surfaces that are oh-so simple to wipe down. The all-in-one living area is another handy feature that guarantees optimum family time, allowing you to converse with the kids even when you’re in the middle of cooking dinner. The bunk beds add to the fun factor of the kids’ room and are bound to make the announcement of bedtime go down a little easier. And the main event? A pool with a built-in playground, a lazy river, and two full-sized water slides. 

Rooms? 2 bedrooms. Sleeps 6 guests. 
Location perks? 15 minutes from the Disney Parks and 30 minutes from Universal Studios. There’s also a Publix supermarket nearby and parking available in Champions Gate. 
Time Out tip: There’s a fitness center available on the premises for adults seeking a sweat session that doesn’t involve running around the kids. 

There are plenty of Airbnbs in Osceola with a pool, but few come close to this resort-style complex made up of luxury units that won’t blow your budget. The boutique townhouses are all individually furnished with an upscale appearance owed to the vaulted ceilings. Plush oversized sofas act as the centrepoint of the living room, set against a wall-mounted flat screen TV and low-hanging statement lighting. The kitchen is slick and contemporary, with top-of-the-range appliances ready to tackle meals of any size. The extended breakfast bar also allows for social mornings surrounded by the smell of freshly cooked pancakes – what could be better? The pool area is just as bougie, with towering palm trees, rows of chic sunbeds and parasols lining the water, and a pool fountain installed for dramatic effect – and let’s not forget the hot tub… Guests also have access to a gym, tennis court, and beach volleyball court, plus a private patio per household with a BBQ grill. 

Rooms? 3 bedrooms. Sleeps 6 guests. 
Location perks? Located in Magic Village, right next to Disney World. A 10-minute drive to ESPN Wild World of Sport Arena.
Time Out tip: Don’t take that full-size laundry room for granted… 

An Osceola vacation rental that feels like home? The owners of this Airbnb have given it a kid-friendly makeover that’s sure to please the tykes. Let's start with the games room: it’s kitted out with a pool table, ping pong, foosball table, and two arcade games – plenty of activities to go around. The youngsters’ bedrooms are playfully themed around Mickey Mouse and the Despicable Me Minions, both featuring bunk beds for that extra bit of fun. The overall look of the property is bright and contemporary, appealing to the aesthetic of most typical modern families. The back yard houses a pool covered by a glass dome, so you can feel like you’re outside while still being protected from the elements. There’s a table and chairs for post-swim snacking, and a gate to give you peace of mind if you have a kid that’s not ready to jump in the water unsupervized. Floaties and toys are available for endless outdoor fun, and serve as a great distraction while you’re busy grilling on the BBQ. 

Rooms? 4 bedrooms. Sleeps 9 guests. 
Location perks? Epcot, Hollywood Studios and Animal Kingdom are all within 15 minutes from the property. 
Time Out tip: If you happen to be a board game family, you’re in luck – there’s a ton here.