The Best Vacation Rentals to Book in Kissimmee, Florida

Just 3mi (4.8km) from Walt Disney World, this seven-bedroom, five-bathroom villa sleeps up to 16 and boasts several themed rooms, including a Star Wars room, a Batman room and a princess room. Perfect for families, the palatial two-story home sits in a gated community and includes an eat-in kitchen, a dining room and a games room complete with pool table, air hockey and Skee-Ball. Outdoors, the villa has a private screened-in pool and hot tub, a garden and a barbecue.

Located in a gated community a three-minute drive from Lake Cecile, this 1,500sqft (139sqm) townhouse sleeps 12. Kids will love the bedrooms themed with Disney characters including Mickey Mouse, Donald Duck and Goofy. The home has a large open-plan kitchen that overlooks the living room. Resort-style amenities located steps from the home include a large pool, fitness center, barbecue grills, basketball and tennis courts, and a clubhouse with pool tables.

As the name suggests, this fairytale-themed private vacation home features four bedrooms with televisions, including one princess-themed and one Cars-themed room. The open-floor plan is convenient for families and offers all the comforts of home: large kitchen, living room, a washer and dryer and a private heated pool. Located less than 4mi (6.4km) from Disney attractions, this lakefront community also features a shared lagoon-style pool, lazy river, tiki bar, fishing dock, canoe/kayak launch, minigolf, tennis courts and sand volleyball court.

This massive eight-bedroom, five-bathroom home in the heart of Kissimmee offers entertaining amenities perfect for large families or family reunions. From a private pool and hot tub to a home theater to a games room with pool table, air hockey and foosball, this holiday home includes everything a resort has and more. Within the gated community, there’s a shared 10,000sqft (929sqm) clubhouse with a pool, spa, lazy river, waterslide, splash pad, poolside dining and bar, minigolf and kayak rentals.

Up to 19 loved ones can enjoy the eight bedrooms, six bathrooms and luxury amenities at this private 4,369sqft (406sqm) villa in the gated vacation rental community of Windsor at Westside. While the home boasts a private pool and spa, the community’s 5,000sqft (465sqm) clubhouse includes two pools with cabanas and waterslide, lazy river, tiki bar, children’s splash pool, gym, cinema, arcade games, tennis, volleyball and multipurpose sports courts.

Located in a gated master planned community, this expansive five bedroom, five bathroom home in Storey Lake has everything needed for fun in the sun, including a private pool and hot tub. The two-story property includes two living rooms, a large kitchen and a washer/dryer. Within the community, you’ll have access to a minigolf course surrounded by a resort-style swimming pool, a fitness center, several lakes for canoeing and kayaking, a sand volleyball court, soccer field, playground and splash park.

This single-family home boasts five bedrooms, including Star Wars– and Disney-themed stays for little ones or the young-at-heart. A private pool and spa add to the vacation vibes. Located in Storey Lake, community amenities include a clubhouse with a tiki bar, a pool with two twisty water slides, a lazy river, splash pad, fitness center, volleyball and sports courts and canoe and kayak rentals.

This action-packed home has nine bedrooms – four are elaborately-themed with Frozen, Toy Story, Mickey and Minnie or Marvel comics – plus a Paw Patrol playroom loft and a Star Wars-themed game room. This ChampionsGate villa features a private pool and spa, but the community also has a 20,000sqft (1,858sqm) clubhouse with a pool, water slides, air-conditioned cabanas, 18-hole golf course, lazy river, splash park, bar, restaurant, gym, cinema, playground, volleyball courts, six tennis courts, and supervised children’s activities.

Located 3mi (4.8km) from Walt Disney World, this gated community is surrounded by conservation woodlands. The secluded neighborhood offers three- and four-bedroom townhouses, four-to-seven-bedroom vacation villas, and pool homes rentable for daily, weekly and long-term stays. Last-minute travelers can get discounts of 10-to-30 percent off, plus barbecue grills and baby equipment are provided for free. Community amenities include a nature walk, sauna, pool, clubhouse, tiki bar, spa, basketball court, volleyball court, tennis courts and playground.

Each of the sumptuously appointed bedrooms in this six-bedroom villa has its own en-suite bathroom and television. Located in the gated Bella Vida community, this home, which includes a Minions-themed bedroom, large kitchen and hot tub, has a cinema, a games room and a large pool deck overlooking a lake. The home is a 10-minute walk to the clubhouse, which has a heated outdoor pool, gym, cinema, fishing lake, sports courts and playground.