16 Best Airbnb Rentals in Kissimmee, Florida - Trips To Discover (2025)

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Chic & Cozy 5-Bedroom Pool Home Near Disney, Gated

Bordering the conservation area, this Kissimmee Airbnb is among the best large properties around town. The fresh air is in excess, the tranquility is guaranteed, and the amenities are excellent. Here, Central Florida’s wilderness is basically your backyard. Profit from the screened private pool with spillover spa, play foosball, pool, table tennis, and XBOX in the game room, and take advantage of airy outdoor areas. There’s a special treat for kids too, the house boasts Marvel and Star Wars-themed rooms. 5 bedrooms and four bathrooms can comfortably host up to 14 people so it’s your top choice for groupholidays.The Airbnb is surrounded by golf courses, and Disney World can be reached in 20 minutes.

Great House in Orlando Kissimmee - 15 Minutes From Disney

Get a taste of classic Florida living with this well-reviewed property. One of the top Airbnb rentals in Kissimmee for families, it has all the space and fun needed for an awesome break. The swimming pool comes with a hot tub so you will have many opportunities to enjoy the sunshine. Spend cheerful time together barbequing and gathering around the dining table in the backyard. Inside, you’ve got a modern, fully equipped kitchen, a washer/dryer, flat-screen TVs in each room, and fast WiFi. As for the location, the Airbnb is situated close to Celebration,15 minutes away from Disney World, and minutes away from such cool neighborhood attractions asOrlando Tree Trek Adventure Park Zip Line,Reunion Resort Water Park, andMystic Dunes Golf Club.

Luxury 5-Bedroom Private Pool Lakeview Home Near Disney

View matters and you’re getting an amazing one with this luxuryKissimmee rental. The idyllic lake will be your vista while staying here. The presence of a heated outdoor pool makes marveling at the panorama even more rewarding. Dine outside during the sunset on your private patio, have a BBQ session, and relax properly after intense days of visiting the theme parks around. The interiors are tastefully created and feature lots of light. There are Disney-themed rooms too, a nice touch to get you in the festive mood. The coolest perk, though, is the access to all the resort facilities of your gated community such as a communal pool, fitness center, full-service restaurant, and the arcade room.

Gathering Paradise with Golf View and Game Room

If a luxurious Florida retreat is something you’re seeking, that’s the property to book. You will stay in a resort-style mansion that doesn’t lack in size and space. Of course, for a proper Kissimmee break, you need a private pool. Here you have one and it comes with a spill-over hot tub for more relaxing moments. More entertainment? There’s a garage game room for that with an Xbox, a pool table, and arcades. What’s really special is a separatetheater loft for movie watching with a sleeper sofa. All the essentials like a huge fully equipped kitchen, two dining areas, AC, and WiFi are here too. The property is part of a gated community and Disney World is a 10-minute drive.

Luxury 4 Bedroom Home with Resort Access Near Disney

With 3,200 square feet of living space,4 bedrooms, and 12 people accommodating capacity – you’re looking at one of the best Airbnb rentals in Kissimmee that boasts chic looks and top amenities. This is the house where you’re able to fully relax soaking in the Florida sunshine. The outdoor pool is an aesthetic statement, and the elevated spill-over hot tub is a neat addition. Reviews compliment the cleanliness, the stylish interiors, and the impeccable privacy. You’ll live within theReunion Resort gated community with the possibility to access all the facilities in the area. That includes 3 golf courses, a water park, and a tennis court. The house is situated right next to the picturesque golf field so the tranquility is guaranteed.

Charming Three Bedroom House with Heated Pool

Straight 5 in reviews with a lot of praise for the host’s attitude and the overall experience, this cottage doesn’t hold back when it comes to Central Florida comfort living. The location is a prestigious residential neighborhood ofBuena Ventura Lakes, the Old Town of Kissimmee is close by, and Disney World is 20 minutes away by car. The property is perfect for outdoor enjoyment; the heated pool is big, and it features a pleasant waterfall. You also have a poolside patio with an obligatory propane BBQ as well as a bar and a cooler. This is a killer combination for cheerful family evenings.

Modern Storey Lake Resort Disney Orlando

Set right off theOsceola Parkway with the picturesque Storey Lake nearby, this Airbnb is a perfect choice for those who’d like to be close to Disney World (it’s just 12 minutes away). With an affordable price tag, numerous positive reviews, and contemporary looks, it’s a gem of the rental scene ofKissimmee. Ideal for families but also perfectly suitable for couples and solo travelers, the apartment comes with2 bedrooms, a patio with a lake view, a fully equipped kitchen, and free parking. The guests have access to the resort’s water park, lake walking trails, fitness center, mini-golf course, and kayak rental. There’s a Target and a Walmart right nearby for shopping.

Encanto Summer Home with Private Pool at Storey Lake

Renting a four-bedroom property is never a bad idea to take advantage of more space during a Florida family outing. This home comes with an added plus of Disney-themed rooms. Encanto and Star Wars characters come alive in the children-friendly bedrooms here. You will have a private pool for splashy fun and a cozy terrace to enjoy the outdoors. The fully equipped kitchen has contemporary amenities and the dining area is large. Moreover, all the resort facilities are accessible to guests. That means that your children will have a blast riding the water slides and swimming in a lazy river at the slash park while the adults will enjoy a drink at a tiki bar.

Amazing 6-Bedroom at Storey Lake, Next to Disney

This 3,200-square-foot home is a dream location for families with children or those who are kids at heart. The game room in the house has an air hockey table, foosball table and large screen television with PlayStation 4. Sleeping up to 16, four out of the six bedrooms have 50” Smart TVs and the house also has a private pool and spa, outdoor dining area and gas grill for cookouts.

Luxury Windsor Hills Condo

You don’t have to let it go in this vacation rental. The two-bedroom, two-bath condo has a Frozen-themed room with lighting that can be dimmed to make a sparkling effect, glitter walls and decorative themed bedding. There’s also a Mickey Mouse-themed bedroom to help the festive feel. The living area is spacious enough for the six guests to dine and relax or enjoy the screened patio, and there’s an in-unit washer and dryer. The community amenities available for guests to use include a game room, heated Olympic-sized pool, water slides, pool table and tennis courts.

What a Vacation House with Private Pool & More

Everything you need for a getaway for up to 10 is in this vacation rental. Outdoors, the home’s screened-in pool, spa and barbecue area will let you enjoy the Florida sun while right across the street is a neighborhood park with a playground for children. Inside, when not using the five bedrooms and four bathrooms, spend time in the game room playing board games, billiards and air hockey.

Find a Little Magic in a Townhouse near Disney and Universal

This modernly styled 2 bedroom, 2 bath townhouse is a comforting place to relax after time at the local theme parks. Located in a gated community, guests can sit by the shared swimming pool, enjoy the waterside, use the fitness center or sit and have a drink and meal at the snack bar. Inside the home, there’s a full-sized kitchen, private hot tub, washer/dryer, and screened patio area to enjoy the weather.

2-Bedroom Condo, Close to Disney, Storey Lake

Centrally located to convention centers, theme parks, shopping, restaurants, and entertainment, this 2 bedroom, 2 bedroom condo is great for families or friend getaways. In a gated complex, guests are welcome to enjoy the shared resort pool, lazy river, volleyball court, water slides, and tiki bar. Once back at the condo the modern kitchen, living area, and back patio help to relax after a long day.

Disney World Vacation Home – The Mouse Townhouse

This two-bedroom, two-bathroom townhouse is great for smaller groups who can’t get enough of a Disney theme. From the couch pillows, wall hangings, kitchen accessories and bedroom linens, you’ll never miss Mickey or Minnie. But it’s not only about the House of the Mouse. Located inside FantasyWorld Resort, guests have access to resort amenities of heated pools, a splash pad, Jacuzzi, playground, batting cages, mini golf, a water park and a pool bar.

Barefootn 1 Bedroom Near Kissimmee Old Town

Located near the shopping, dining and ride area of Old Town, this 1 bedroom, 1 bathroom unit sleeps four and offers a kitchenette, two beds, and a washer/dryer to help guests relax after spending the day out. On-site shared amenities included a heated pool, grill, playground, and hot tub.

Sunsation Destination - 1 Bedroom Villa-2nd Floor

Amenities abound in this 1 bedroom, 1 bathroom unit that’s perfect for a couple, small family or group of friends. Approximately 10 miles from Disney World, it’s close enough to head to the theme parks for the day and also has enough to do if you would like to stay home. The community offers mini-golf, swimming pools, a playground, a children’s water splash pad area and a basketball court. The home itself has a dining area, full-sized kitchen, and washer/dryer and is located close to restaurants and stores.