Seeking an upscale villa rental in Kissimmee? Browse our curated index of private luxury estates, complete with spacious floorplans and premium amenities. Easily compare verified listings for a truly refined holiday escape.
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Hot tubs, Places to stay
Exceptional
1 reviews
AC, Arcade, Crib, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen
Superb
7 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Jacuzzis, Places to stay
AC, Arcade, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen
Exceptional
192 reviews
Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals
Very Good
68 reviews
AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Internet, Kitchen, Laundry
Very Good
74 reviews
Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay
Superb
4 reviews
AC, Balcony, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry
Review score
1 reviews
Internet, Air Conditioner, Pool, Parking, Child Friendly
Good
1 reviews
AC, Arcade, Barbecue, Dryer, Fitness Equipment, Internet, Kitchen, Laundry, Living Area
Very Good
15 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family
AC, Barbecue, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Living Area
Fabulous
8 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs
AC, Arcade, Barbecue, Dryer, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet
Review score
1 reviews
Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Hot tubs
AC, Dryer, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking, Patio
AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry
Superb
54 reviews
AC, Dryer, Heater, Internet, Laundry, No Smoking
AC, Arcade, Business Services, Dryer, Extra Bed, Fitness Equipment, Free Parking, Heater, Hot Tub
Superb
75 reviews
AC, Arcade, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Living Area
Fabulous
11 reviews
AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer
Exceptional
1 reviews
Pro Tip:
OwnerDirectVacationRental aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Villa Rentals in Kissimmee.
OwnerDirectVacationRental can help you find hotels, resorts, and rentals near many of 's top attractions, neighborhoods, and points of interest.
What makes our villa rentals stand out?
Every villa rentals shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Compare a range of properties and find fair, transparent pricing—no hidden fees.
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
Some of the best villa rentals in Kissimmee are:
There are a lot of options in Kissimmee. If you plan on staying in the Kissimmee area, consider making a reservation for a few nights at one of these properties as these have been rated the top Villa Rentals in Kissimmee
You can currently explore 1101 verified villa rentals in Kissimmee. Our listings are sourced from multiple leading booking platforms, giving you a broad and up-to-date selection of luxury and private villas in one place.
Villa prices in Kissimmee vary depending on the season, location, and amenities. Rates typically start from around $90 per night, with premium properties costing more during peak travel periods. Comparing options across different platforms can help you find the best value for your dates.
Many villas in Kissimmee are designed for privacy and comfort, and a large number of them feature private pools. You can easily filter your search to find villas with pools, helping you choose the perfect stay for relaxation or group travel in Kissimmee.
Yes, Kissimmee offers a wide range of villas ideal for group stays. Many properties include 3 or more bedrooms, making them well-suited for family gatherings, events, or trips with friends. You can filter by bedroom count to quickly find options that match your group size.
For popular travel periods, it’s generally recommended to book your Kissimmee villa around 60 to 90 days in advance to secure the best selection. However, since we compare 10+ sites, it’s still possible to find great last-minute options even 2 to 4 weeks before your trip.
Villas in Kissimmee often include highly sought-after amenities such as Pool, Fireplace/Heating, and Wellness Facilities. These features enhance comfort and convenience, making them especially popular among travelers visiting Kissimmee.
To discover top-rated villas in Kissimmee, you can sort listings by guest ratings and reviews. Our platform aggregates feedback from multiple trusted sources, helping you identify highly rated properties based on real guest experiences. Use the 'Rating' filter above to start your search.