The Best Vacation Rentals to Book in Kissimmee, Florida

Kick back after a long day enjoying thrilling theme parks in your very own Kissimmee vacation rental
Kick back after a long day enjoying thrilling theme parks in your very own Kissimmee vacation rental | Courtesy of Cruden Villa Champions Gate 8833 / Expedia.com
Photo of Lauren Mack
7 December 2021
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Once a small trading post, Kissimmee is now a theme park hotspot in central Florida. Travelers seeking alternatives to hotels, motels and timeshares have thousands of vacation rentals to consider in Kissimmee. These come in all sizes with amenities that rival traditional hotels and resorts – many even feature themed bedrooms and private pools to amp up the fun. Read on for our pick of the best vacation rentals in Kissimmee, Florida – all bookable with Culture Trip.

Themed Luxury Villa, for movie-loving families

A seating area with gray sofas and a gray wood kitchen inside the Themed Luxury Villa
Courtesy of Themed Luxury Villa / Expedia.com

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.

Luxury 4BR Townhome - Gated Resort, for Disney fans

A seating area with a gray corner sofa and a dining table with four chairs inside the Luxury 4BR Townhome
Courtesy of Luxury 4BR Townhome - Gated Resort / Expedia.com
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.

Enchanted Storey Lake Villa, for folks who believe in fairytales

An L-shaped swimming pool covered by a glass roof at Enchanted Storey Lake Villa
Courtesy of Enchanted Storey Lake Villa / Expedia.com
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.

Royal Mansion at Storey Lakes by Orlando Short Term, for an entertaining family reunion

A large living area with a beige corner sofa and two blue armchairs in the Royal Mansion at Storey Lakes by Orlando Short Term
Courtesy of Royal Mansion at Storey Lakes by Orlando Short Term / Expedia.com

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.

Bengal Court Villa Windsor At Westside 1, for multi-family group getaways

Living area with gray seating, a large dining table with white chairs, and a large kitchen inside Bengal Court Villa Windsor At Westside 1
Courtesy of Bengal Court Villa Windsor At Westside 1 / Expedia.com

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.

Bookmark Villa Storey Lake 1, for fun in the sun

A seating area with high ceilings, white walls and gray furnishings inside Bookmark Villa Storey Lake 1
Courtesy of Bookmark Villa Storey Lake 1 / Expedia.com

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.

Dream Vacation Home Close to Disney Sl4839, for multi-generational families

A living area with a gray corner sofa and kitchen inside Dream Vacation Home Close to Disney
Courtesy of Dream Vacation Home Close to Disney / Expedia.com

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.

Cruden Villa Champions Gate 8833, for movie buffs

A large terrace area with seating, sunbeds and an outdoor swimming pool at Cruden Villa Champions Gate 8833
Courtesy of Cruden Villa Champions Gate 8833 / Expedia.com

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.

Emerald Island Resort by Nova, for deal seekers

A large swimming pool covered by a glass roof, with sunbeds and pool toys, at Emerald Island Resort by Nova
Courtesy of Emerald Island Resort by Nova / Expedia.com
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.

6 Bedroom Villa Bella Vida, for privacy and pampering

A living area with a large gray corner sofa, two armchairs, and a large kitchen inside the 6 Bedroom Villa Bella Vida
Courtesy of 6 Bedroom Villa Bella Vida / Expedia.com
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.

For some budget-friendly options, discover our guide to the best cheap hotels in Kissimmee and book now on Culture Trip.

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