Top Kissimmee Vacation Home Rentals for Families

First up, let's talk about Reunion Resort Rentals, where the fun meter is perpetually set to "maximum."

• IN THE HOUSE: Imagine watching their eyes light up as they walk into dreamy rooms themed around camping adventures, the beach, or outer space. Your kids will flip when they see the game rooms, bursting with entertainment options that might make them forget their phones – for a moment, anyway! When it’s time to cool off, the private pool is just a few steps away, perfect for a refreshing dip on a sun-soaked afternoon. And for those cozy family movie nights, home theaters with plush seating and surround sound make Netflix feel like a red-carpet premier.
• ONSITE: The water park's twisting slides and lazy river offer splash-tastic fun, while poolside food and beverage service mean you never have to leave your lounge chair. Lawn games, bike rentals, and multiple dining options round out this paradise.
• SPECIAL OFFERS: Check into deals for Florida and Georgia residents, AAA and AARP members, military families, and more.

Next, we whisk you away to Bear’s Den Resort Orlando, a luxurious retreat where even the family pet gets a taste of the high life!

• IN THE HOUSE: Balance out action-packed theme park days with a few hours in the private movie theater or check out the game rooms kitted out with everything from foosball to the latest video games. Step out back to the private pool made for cannonball contests.
• ONSITE: Spend some time at Golden Bear Park, which boasts a playground for the kids and a dog park perfect for your family’s furry bestie. Complimentary access to Reunion Resort’s water park, lazy river, and pool games offers more to explore with your family. Speed things up with golf cart and bike rentals, including bikes with training wheels for the wee ones. Check out our roundup of the top amenities Bear’s Den offers!
• SPECIAL OFFERS & PERKS: Complimentary Disney transportation and special savings for Florida and Georgia residents and make this resort even more irresistible.

Seeking a serene yet thrill-packed escape? Check into Regal Oaks, where spacious 2, 3, and 4-bedroom townhomes offer a relaxing retreat popular with families.

• IN THE HOUSE: Fully equipped kitchens make big meals a breeze, while in-home washers and dryers ensure you can pack light and wash as you go, saving that oh-so-sacred trunk space for souvenirs.
• ONSITE: The heated community pool makes for comfortable socializing while the waterslide complex is perfect for high-energy kids and sunny do-nothing days. Your little homebodies will love the coolness of the clubhouse arcade with its variety of games. Dining at The Hub, a family-friendly sports bar and grill, is just a short stroll away, and you’ll also be within walking distance of Old Town Entertainment District, a hub for shopping, dining, and entertainment (including wild rides).
• SPECIAL OFFERS: With special deals for Florida and Georgia residents, Regal Oaks is a gem for family vacations.

For those who want it all at a price that won't break the bank, Elite Vacation Homes delivers.

• IN THE HOUSE: Offering a range of rental options from single-family homes to condos, each stay promises comfort, style, and easy access to loads of amenities. Private pools and hot tubs invite total relaxation, while in-house game rooms keep the kids busy for hours.
• ONSITE: Water views add a serene backdrop to your stay, perfect for those Instagram-worthy moments. Onsite amenities vary based on the property location, ensuring there's something for everyone.
• SPECIAL OFFERS: Florida resident deals, AAA and AARP discounts, military discounts, and a loyalty program with a Smart Pay Plan sweeten the deal, making Elite Vacation Homes a savvy choice for families.

Blend the charm of a residential neighborhood with the convenience of resort amenities and – poof! – you have summoned Encore Resort at Reunion.

• IN THE HOUSE: Most homes at Encore offer a private pool, and themed rooms (think cartoons, superheroes, and bright colors) are available to enhance your stay.
• ONSITE: Take the fam to the community water park, where you can glide down a 50-foot waterslide while the littles kick around the splash zone. The area offers multiple cabanas to escape the Florida sun. Flex your pickleball skills on one of the many sports courts or drop your last quarter in at the arcade – the activities are endless! And if you’re too tired to leave for dinner, check out the onsite dining option for delicious and convenient meals.
• SPECIAL OFFERS: With special pricing for Florida and Georgia residents, discounts for military personnel and first responders, and a “55+ and Fabulous” senior discount, Encore Resort Homes is the perfect place for multi-generational family vacations.

Swing that mouse ear this way and listen closely – THIS is where the magic happens. Welcome to Magic Village Views, where modern luxury comes to life in fully furnished 3- and 4-bedroom vacation rentals.

• IN THE HOUSE: Level up your home-away-from-home game with these sophisticated villas, equipped with an expansive full kitchen, washer and dryer, and outdoor living spaces perfect for grilling up a home-cooked meal.
• ONSITE: Check out the heated outdoor pool and hot tub for total relaxation. Swing by the restaurant for a quick bite after working out at the fitness center – it’s all here. And when the parents are ready for a break, Magic Village Views offers childcare to ensure that the adults can enjoy some alone time, knowing their little ones are in good hands.
• SPECIAL OFFERS: Florida and Georgia residents, rejoice! Your discount is alive and well here, along with military and AAA members. Visit the partner website for seasonal and limited-time offers such as theme park deals and in-house massage services.

Magical Vacation Homes offers an extensive network of properties, including those located at the resort areas listed above as well as ultra high-end properties.

• IN THE HOUSE: Some homes feature themed bedrooms – from wizarding wonders to whimsical fairy tales that ignite the imagination – as well as game rooms, home theaters, and stunning private pools.
• ONSITE: Amenities vary by property, but the company’s concierge services ensure your stay is seamless and, well, magical!
• SPECIAL OFFERS: Save with Florida resident deals, seasonal sales, repeat visitor discounts, military and first responder discounts, and more.

Jeeves Florida Rentals provides a large network of homes and condos and offers many properties located in Central Florida's most sought-after vacation resorts such as Reunion, Encore, Solterra, Solara, and ChampionsGate.

• IN THE HOUSE: Spacious resort-style rentals feature themed bedrooms, game rooms, home theaters, and private pools that make every stay unforgettable. Find everything from 2- and 3-bedroom condos to sprawling vacation homes with up to 12 bedrooms!
• ONSITE: Amenities vary, but the level of service is consistently high. Additional services such as access to cribs, highchairs, and strollers are available, as well as arranging character visits and professional photo shoots to meet every family’s needs.
• SPECIAL OFFERS: Seasonal promotions, advance purchase promos, and extended stay offers make Jeeves Florida Rentals an attractive option for families planning longer vacations.