Choose from 32,931 vacation rentals located in Osceola County, Florida. Top filters in Osceola County include Air conditioner, Kitchen / Kitchenette, and Internet / Wifi. Prices range from $39 to $20,000 per night. Our most popular vacation rental types near Osceola County are House and Hotel.

Top vacation rentals in Osceola County

The lanai has a table that seats 8, privacy bushes, 4 lounge chairs & BBQ
5.0
Outstanding(284 Reviews)
House
 in Kissimmee
Top-Rated Amazing Villa! Salt💧Pool, Game Room + Pool Heat, BBQ & Baby Gear
14 guests · 6 bedrooms · 4 baths
Garden · Pool · Pets allowed

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Osceola County, at $377 per night for your next great vacation.

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3.9
Good(1,265 Reviews)
Resort
 in Orlando
Regal Oaks Resort Vacation Townhomes by IDILIQ
Garden · Pool · Pets allowed

Enjoy the best of Osceola County in our Resort, Regal Oaks Resort Vacation Townhomes by IDILIQ. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Orbit One Vacation Villas Exterior 1
4.7
Outstanding(408 Reviews)
Condo
 in Kissimmee
Family-Friendly Condo w\/ Resort Pool & Just 1 Mile From Disney!
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

The best choice in Osceola County for Condo, for $128 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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4.5
Excellent(24 Reviews)
House
 in Kissimmee
Disney Dream with Hot Tub, Pool, Xbox, Games Room, Lakeview, 10 min to Disney, Clubhouse
Garden · Pool · Kitchen / Kitchenette

Experience vacation in Osceola County with our House, Disney Dream with Hot Tub, Pool, Xbox, Games Room, Lakeview, 10 min to Disney, Clubhouse. Enjoy amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

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Search by amenity

Explore vacation rentals with the most popular amenities in Osceola County

Vacation rentals with air conditioning in Osceola County

Parkway Pool Area 2
4.5
Excellent(444 Reviews)
Condo
 in Kissimmee
Lovely Condo Just 1 Mile From Disney w\/ Resort Pool, WiFi & More
6 guests · 2 bedrooms · 2 baths
Pool · Kitchen / Kitchenette · Air conditioner

Soak up the beauty of Osceola County in our Condo, Lovely Condo Just 1 Mile From Disney w\/ Resort Pool, WiFi & More. With a range of amenities such as Air conditioner, Dishwasher and Internet / Wifi, you'll feel right at home.

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Pool
4.9
Outstanding(263 Reviews)
House
 in Kissimmee
Water View - Pool & Spa - 3.5 miles to Disney - WiFi - BBQ
8 guests · 4 bedrooms · 3 baths
Garden · Pool · Kitchen / Kitchenette

Looking for a House in Osceola County, this House for $188 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

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villa
5.0
Outstanding(235 Reviews)
Villa
 in Kissimmee
Amazing villa close to Disney with 5* Reviews
6 guests · 3 bedrooms · 3 baths
Garden · Pool · Kitchen / Kitchenette

When traveling to Osceola County, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $165 per night.

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3.2
Average(1,054 Reviews)
Hotel
 in Orlando
3star
Comfort Inn & Suites Kissimmee by the Parks
Pool · Kitchen / Kitchenette · Air conditioner

This Hotel for $171 in Osceola County, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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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 Haines City 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-$20,000. The average price for rentals in Osceola County is $222 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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