Osceola County Holiday Rentals

Compare Villas, Resorts, & Rentals in Osceola County, Florida, USA

10.0 (3 Reviews)
2 Bedrooms 8 Guests
From US $228 per night
New
5 Bedrooms 10 Guests
From US $160 per night
10.0 (1 Review)
2 Bedrooms 6 Guests
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10.0 (11 Reviews)
5 Bedrooms 12 Guests
10.0 (1 Review)
2 Bedrooms 8 Guests
10.0 (2 Reviews)
2 Bedrooms 6 Guests
9.6 (5 Reviews)
1 Bedroom 6 Guests
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10.0 (10 Reviews)
5 Bedrooms 10 Guests
|
10.0 (8 Reviews)
4 Bedrooms 10 Guests
From US $224 per night
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10.0 (7 Reviews)
5 Bedrooms 10 Guests
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10.0 (6 Reviews)
9 Bedrooms 21 Guests
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10.0 (6 Reviews)
6 Bedrooms 14 Guests
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10.0 (6 Reviews)
3 Bedrooms 6 Guests
From US $223 per night
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10.0 (6 Reviews)
3 Bedrooms 8 Guests
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10.0 (6 Reviews)
4 Bedrooms 8 Guests
From US $125 per night
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10.0 (6 Reviews)
4 Bedrooms 14 Guests
10.0 (6 Reviews)
4 Bedrooms 9 Guests
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10.0 (5 Reviews)
6 Bedrooms 18 Guests
9.8 (70 Reviews)
1 Bedroom 4 Guests
9.8 (34 Reviews)
1 Bedroom 4 Guests
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10.0 (5 Reviews)
4 Bedrooms 10 Guests
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10.0 (5 Reviews)
4 Bedrooms 11 Guests
New 5 BD En-suites, Game Room, Pool, Sleeps 14, Disney
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10.0 (5 Reviews)
3 Bedrooms 8 Guests
From US $157 per night
New
2 Bedrooms 5 Guests
New Fun 9Bd Pool Home with Games and Themed Rooms-1576
From US $242 per night
10.0 (5 Reviews)
4 Bedrooms 14 Guests
9.0 (2 Reviews)
1 Bedroom 4 Guests
New 9 Bedrooms/5 Bathrooms/Storey Lake (2867SC)
New
9 Bedrooms 22 Guests
From US $162 per night
10.0 (5 Reviews)
3 Bedrooms 10 Guests
New
1 Bedroom 4 Guests
New 2025 NEW 10 Bedrooms At Windsor Cay
New
10 Bedrooms 24 Guests
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10.0 (4 Reviews)
4 Bedrooms 8 Guests
New 10 Bedrooms/8 Bathrooms/Windsor Cay (15922CC)
New
10 Bedrooms 24 Guests
From US $282 per night
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10.0 (4 Reviews)
5 Bedrooms 14 Guests
From US $200 per night
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10.0 (4 Reviews)
4 Bedrooms 8 Guests
New 5 Bedrooms/5 Bathrooms/Paradise (2924BP)
New
5 Bedrooms 18 Guests
New 4533 Magical 9‑Bed Storey Lake Villa w/Private Pool
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10.0 (4 Reviews)
3 Bedrooms 10 Guests
New 16109 Amazing House With Pool 5/4.5
New
5 Bedrooms 13 Guests
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10.0 (4 Reviews)
4 Bedrooms 10 Guests
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10.0 (4 Reviews)
4 Bedrooms 10 Guests
New Emeralds family getaways
From US $527 per night
New
6 Bedrooms 2 Guests
From US $102 per night
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10.0 (4 Reviews)
1 Bedroom 3 Guests
10.0 (4 Reviews)
1 Bedroom 13 Guests

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

Discover more than 42841 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 1726.61 ft², with nightly prices averaging US $377.

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.

Frequently Asked Questions About Osceola County?

What are the top holiday rentals in Osceola County?

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

As of 2025, Casai boasts over 42841 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.