Osceola County Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes 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
10.0 (1 Review)
2 Bedrooms 8 Guests
|
10.0 (10 Reviews)
5 Bedrooms 10 Guests
10.0 (2 Reviews)
2 Bedrooms 6 Guests
9.6 (5 Reviews)
1 Bedroom 6 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
|
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
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10.0 (5 Reviews)
4 Bedrooms 10 Guests
9.8 (34 Reviews)
1 Bedroom 4 Guests
|
10.0 (5 Reviews)
4 Bedrooms 11 Guests
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10.0 (5 Reviews)
3 Bedrooms 8 Guests
New 5 BD En-suites, Game Room, Pool, Sleeps 14, Disney
From US $242 per night
10.0 (5 Reviews)
4 Bedrooms 14 Guests
From US $157 per night
New
2 Bedrooms 5 Guests
New Fun 9Bd Pool Home with Games and Themed Rooms-1576
From US $162 per night
10.0 (5 Reviews)
3 Bedrooms 10 Guests
9.0 (2 Reviews)
1 Bedroom 4 Guests
New 9 Bedrooms/5 Bathrooms/Storey Lake (2867SC)
New
9 Bedrooms 22 Guests
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10.0 (4 Reviews)
4 Bedrooms 8 Guests
New
1 Bedroom 4 Guests
New 2025 NEW 10 Bedrooms At Windsor Cay
New
10 Bedrooms 24 Guests
From US $282 per night
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10.0 (4 Reviews)
5 Bedrooms 14 Guests
New 10 Bedrooms/8 Bathrooms/Windsor Cay (15922CC)
New
10 Bedrooms 24 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
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10.0 (4 Reviews)
3 Bedrooms 10 Guests
New Unforgettable Themed 9BR House! Game Room & Pool
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10.0 (4 Reviews)
4 Bedrooms 10 Guests
New 4533 Magical 9‑Bed Storey Lake Villa w/Private Pool
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10.0 (4 Reviews)
4 Bedrooms 10 Guests
New 16109 Amazing House With Pool 5/4.5
New
5 Bedrooms 13 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
New Emeralds family getaways
From US $527 per night
New
6 Bedrooms 2 Guests
10.0 (4 Reviews)
3 Bedrooms 8 Guests

About Osceola County Vacation Rentals

With more than 42695 Osceola County vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Osceola County.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Osceola County, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Osceola County. Places to stay near Osceola County are 1725.55 ft² on average, with prices averaging US $378 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Osceola County with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Osceola County?

What are the top vacation rentals in Osceola County?

How many Rentbyowner vacation rentals are available in Osceola County?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 42695 in the Osceola County area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Osceola County.