Kissimmee’s Most Fun-Yet-Affordable Vacation Homes

Step into the Heritage Crossing Retreat, where your wallet will thank you and your family will cheer. This three-bedroom, two-bath condo offers access to Reunion Resort's stellar amenities, including a water park, onsite restaurants, three signature golf courses, and a shuttle service. Nestled on the third floor with elevator access, this more than 1,400-square-foot condo overlooks the Arnold Palmer golf course and features modern furnishings. Two bedrooms boast king beds, while the third has two full beds, providing ample space for everyone. Nightly rates start at an unbelievable $69 before taxes and fees.

Welcome to The Jungle Journey at Reunion Resort, where kids' imaginations run wild! This three-bedroom, three-bath townhome spans more than 2,000 square feet and features a jungle-themed room complete with bright decor, a slide from the top bunk, and a PS4 gaming system. Although it doesn’t include resort membership, guests can still enjoy public resort amenities like restaurants and pools. Two bedrooms come with king beds, and the third room has bunk beds with full-size mattresses. Rates for this adventure start at $136 per night before taxes and fees.

Ready for a relaxing retreat with a splash of excitement? The Oasis Escape at The Retreat is your go-to. This four-bedroom, three-bath townhouse features a private screened-in pool and a galactic-themed kids’ room. With access to The Retreat’s amenities such as a lazy river, golf course, movie theater, and playground, the fun never stops. The 1,900-square-foot townhome includes two main-floor bedrooms with king beds and two upstairs rooms, one with a twin bed and the other with twin bunk beds. Enjoy all this starting at $121 per night before taxes and fees and found on the Magical Vacation Homes.

For those traveling with a larger group, The Spacious Villa at The Retreat is a dream come true. This six-bedroom, six-bath villa boasts more than 3,300 square feet of space and can host up to 12 guests. With a private screened-in pool, game room featuring a pool table and air hockey, and access to resort amenities like a lazy river and playground, everyone will have a blast. The villa’s deep, comfortable furnishings and fully equipped kitchen make it a perfect home away from home. Nightly rates begin at $163 before taxes and fees and found on Magical Vacation Homes.

Just two miles from Walt Disney World® Resort, the Magical Villa at Windsor Hills is the ideal base for your adventures. This five-bedroom, five-bath villa offers nearly 2,500 square feet of space, accommodating up to 10 guests. It features a private pool, galaxy-themed game room, and proximity to all the magic. Three downstairs bedrooms come with king beds, while two upstairs rooms have twin beds for the kids, one of which features bunk beds. Rates start at $145 per night before taxes and fees.

Only 15 minutes from Walt Disney World® Resort, The Airy Hideaway at Solara is packed with fun and games. This eight-bedroom, six-bath house spans more than 4,000 square feet, making it perfect for large family reunions or team retreats. It includes two imaginatively themed children’s rooms, a fully outfitted game loft with arcade games, a theater room with recliners, and a screened-in pool and patio. The house can accommodate up to 18 guests, with five bedrooms featuring king beds, one bedroom with two full beds, one room with twin bunks, and another room with two twin bunks. Nightly rates start at $313 before taxes and fees and found on Jeeves Florida Rentals.

Embrace nature at the Woodside Villa, where the large screened-in pool backs up to a wooded view. This six-bedroom, three-bath villa in the Crescent Lakes community offers more than 2,600 square feet of space and can sleep up to 12 guests. It includes a game room with foosball and pool tables, and the community features two sets of on-site facilities, each with a children’s play area and a covered BBQ area. One facility has a basketball court, while the other has tennis courts, and a fitness trail. Enjoy all this from $158 per night before taxes and fees and found on Magical Vacation Homes.

Last but certainly not least, the Beach Palm Villa brings island vibes to your vacation. Located in the gated community of Paradise Palms, this four-bedroom, three-bath villa is themed to ensure visitors have a great time. The first floor boasts bright, fun colors and inviting rooms with an island/coastal theme, while the kids' rooms are adorned with popular animated characters and custom LED lighting. Guests have access to a large lagoon-style communal pool, Jacuzzis, a splash pad, a tiki bar, and a club house with a fitness center, arcade, theater, and more. The villa offers more than 1,900 square feet of space and can house up to eight guests. Rates start at $116 per night before taxes and fees and found on Magical Vacation Homes.