42563+ Private Villas and Holiday Rentals in Osceola County |
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Osceola County Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Osceola County

Discover more than 42563 vacation rentals available in Osceola County. 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 Osceola County.

Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Osceola County, 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 Osceola County. On average, places to stay near Osceola County offer 1726.86 ft², with nightly prices averaging GB £280.

With Casai, finding and comparing holiday rentals in Osceola County is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.

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Top Accommodation Types in Osceola County

Type Count
Vacation Homes 27039
Villas 6463
Holiday Apartments 3759
Cottages 388

Use these Quick Filters to Find a Holiday Rental in Osceola County

★ 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 Osceola County.

Weather in Osceola County, FL

View the weather forecast for Osceola County before booking your Osceola County Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Osceola County, FL

Casai offers a large selection of top attractions around Osceola County . Research things to do on your vacation before you visit Osceola County.


Old Town
ESPN Wide World of Sports
Osceola Heritage Park
Silver Spurs Arena
Kissimmee Lakefront Park
Mystic Dunes Golf Club
Medieval Times
ChampionsGate Golf Club
Fun Spot America
Reunion Resort Golf Course
Lake Tohopekaliga
Give Kids the World Village
192 Flea Market
Braves Spring Training
Osceola Performing Arts Center
Kissimmee Civic Center
Boggy Creek Airboat Rides
Capone's Dinner Show
Osceola Regional Medical Center
Austin-Tindall Regional Park
Skate Reflections
Falcon's Fire Golf Club
Celebration Golf Club
Kissimmee Go-Karts
Houston Astros Spring Training
Alligator Lake
Kissimmee Bay Country Club
Tupperware Center
Disney Wilderness Preserve
Congo River Golf

Other Places to Stay in Osceola County, FL


Kissimmee 29,464 Properties
Disney's Maingate West 20,840 Properties
Four Corners 19,936 Properties
West Kissimmee 17,693 Properties
Historic Downtown Kissimmee 8,815 Properties
Reunion 2,169 Properties
Windsor Hills 1,661 Properties
Disney's Maingate East 1,223 Properties
Windsor Palms 972 Properties
Bellavida 269 Properties
Lake Berkley 145 Properties
Buena Ventura Lakes 123 Properties

Frequently Asked Questions About Osceola County?

What are the top holiday rentals in Osceola County?

With numerous options available in Osceola County, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Osceola County:

How many holiday rentals have private pools in Osceola County?

Discover a selection of holiday rentals with private pools near Osceola County 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.

Which holiday homes in Osceola County are best for families?

If you're searching for a family-friendly holiday home in Osceola County, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Osceola County:

How many Casai.uk holiday rentals are available in Osceola County?

As of 2025, Casai boasts over 42563 properties listed in the Osceola County area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Osceola County.


People Also Ask

There are 42563 Osceola County, FL Holiday Rentals

Recently Booked Holiday Rentals in Osceola County