Kissimmee Holiday Rentals
About Casai's Private Villas and Holiday Rentals in Kissimmee
Discover more than 10936 vacation rentals available in Kissimmee. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Kissimmee.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Kissimmee, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Kissimmee. On average, places to stay near Kissimmee offer 2551.12 ft², with nightly prices averaging US $421.
With Casai, finding and comparing holiday rentals in Kissimmee is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
Top Accommodation Types in Kissimmee
| Type | Count |
|---|---|
| Vacation Homes | 7539 |
| Villas | 1598 |
| Holiday Apartments | 1354 |
| Cottages | 90 |
Use these Quick Filters to Find a Holiday Rental in Kissimmee
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Kissimmee.
Weather in Kissimmee, FL
View the weather forecast for Kissimmee before booking your Kissimmee Vacation Rentals to confirm your best time to go.
Top Attractions Around Kissimmee, FL
Casai offers a large selection of top attractions around Kissimmee . Research things to do on your vacation before you visit Kissimmee.
Other Places to Stay in Kissimmee, FL
Frequently Asked Questions About Kissimmee?
What are the top holiday rentals in Kissimmee?
With numerous options available in Kissimmee, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Kissimmee:
- Incredible 6BR Villa by Disney Private Pool Games
- Affordable Luxury Home Near Walt Disney World - Sunshine Villa at Glenbrook Resort, Orlando, Florida
- The Reserve at Summer Bay Orlando
- Elegant Villa wPrivate PoolSpa Game Room
- 2971 Castaway Lane
- Comfy Modern House w Pool Perfect Location
- Its A Dream Family Vacation Rental - Minutes from Disney
- 650 Lasso Drive
- Amazing 8br w pool theater game room by Disney
- Four Bedrooms Home with Pool 3079
How many holiday rentals have private pools in Kissimmee?
Discover a selection of holiday rentals with private pools near Kissimmee with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- 1056 LS - Luxury 4BR3BA - Champions Gate Bliss
- Formosa Valley Resort by UNE Homes
- Family 4BR w Private Pool near Disney Parks
- Doppio Westside
Which holiday homes in Kissimmee are best for families?
If you're searching for a family-friendly holiday home in Kissimmee, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Kissimmee:
- Spacious 4BR Home Themed Rooms, Pool, Near Disney
- Townhome With Private Pool, BBQ & Free Waterpark!
- 1056 LS - Luxury 4BR3BA - Champions Gate Bliss
How many Casai.com holiday rentals are available in Kissimmee?
As of 2026, Casai boasts over 10936 properties listed in the Kissimmee area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Kissimmee.
Nearby Neighborhood (16)
| Neighborhood | Property Count |
|---|---|
| West Kissimmee Vacation Rentals in Orlando, Florida | 15792 |
| Historic Downtown Kissimmee Vacation Rentals in Orlando, Florida | 7708 |
| Windsor Hills Vacation Rentals in Orlando, Florida | 1493 |
| Windsor Palms Vacation Rentals in Orlando, Florida | 800 |
| Bay Lake Vacation Rentals in Orlando, Florida | 724 |
| Bellavida Vacation Rentals in Orlando, Florida | 252 |
| Lake Berkley Vacation Rentals in Orlando, Florida | 170 |
| Orange Lake Vacation Rentals in Orlando, Florida | 97 |
| Crystal Cove Vacation Rentals in Orlando, Florida | 89 |
| Crescent Lakes Vacation Rentals in Orlando, Florida | 81 |
| Indian Point Vacation Rentals in Orlando, Florida | 56 |
| Crestwynd Bay Vacation Rentals in Orlando, Florida | 51 |
| Trafalgar Village Vacation Rentals in Orlando, Florida | 42 |
| Calabria Vacation Rentals in Orlando, Florida | 39 |
| Mill Run Vacation Rentals in Orlando, Florida | 773 |
| Windward Cay Vacation Rentals in Orlando, Florida | 15943 |
