Choose from 38,697 vacation rentals located in Osceola County, Florida. Top filters in Osceola County include Air conditioner, Kitchen or Kitchenette, and Internet / Wifi. Prices range from $39 to $22,779 per night. Our most popular vacation rental types near Osceola County are House and Hotel.

Top vacation rentals in Osceola County

Pool view
4.3
Excellent(1,930 Reviews)
Comfort Suites Maingate East
Hotel
 in Orlando
3star
1 king bed, 1 sofa bed
Pool · Kitchen or Kitchenette · Air conditioner

This attractive Hotel in Osceola County, $101 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Dining
4.7
Outstanding(458 Reviews)
Family-Friendly Condo w/ Resort Pool & Just 1 Mile From Disney!
Apartment
 in Kissimmee
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen or Kitchenette · Air conditioner

The best choice in Osceola County for Apartment, for $143 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Property view
3.8
Good(7 Reviews)
Aquamarine Hideaway
Villa
 in Kissimmee
Garden · Pool · Kitchen or Kitchenette

Soak up the beauty of Osceola County in our Villa, Aquamarine Hideaway. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.

$$$$
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Bird's eye view
4.5
Excellent(9 Reviews)
I - New 4 Bedroom Home - 5 Miles to Disney - Free Water Park - Private Pool
House
 in Kissimmee
Pool · Kitchen or Kitchenette · Air conditioner

Looking for a memorable stay in Osceola County? Our House might just be what you're looking for. Enjoy amenities including Air conditioner, Dishwasher and Fireplace, and more during your stay.

$$$$
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Vacation rentals with air conditioning in Osceola County

Exterior
4.9
Outstanding(281 Reviews)
Water View - Pool & Spa - 3.5 miles to Disney - WiFi - BBQ
House
 in Kissimmee
8 guests · 4 bedrooms · 3 baths
Garden · Pool · Kitchen or Kitchenette

Looking for a House in Osceola County, this House for $248 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

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Pool
4.8
Outstanding(315 Reviews)
Ultimate Lakeview Villa with Everything!
Villa
 in Kissimmee
19 guests · 8 bedrooms · 5 baths
Pool · Kitchen or Kitchenette · Air conditioner

The best choice in Osceola County for Villa, for $573 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property building
4.5
Excellent(5,552 Reviews)
Celebration Suites
Resort
 in Orlando
3 full beds
Garden · Pool · Pets allowed

This Resort for $101 in Osceola County, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Property building, Day
Rodeway Inn Davenport-Champions Gate
Inn
 in Davenport
2 full beds
Pool · Pets allowed · Kitchen or Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Osceola County at Rodeway Inn Davenport-Champions Gate for $92 for your next trip.

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Osceola County

Osceola County travel guide

Let us help you plan your perfect Osceola County vacation. Our travel guide highlights things to do, places to see, favorite vacation rental amenities in Osceola County, and more.

Frequently asked questions

What are the top travel destinations in Osceola County

Kissimmee, Windsor Hills, and Loughman are the top three destinations to travel in Osceola County.

What is the price range for rentals in Osceola County?

Vacation rentals in Osceola County have a price range between $39-$22,779. The average price for rentals in Osceola County is $288 per night.

How many cities have available rentals in Osceola County?

There are 14 destinations with available rentals in Osceola County.

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