Vacation Rentals in Osceola County: 36,500+ properties

Choose from 36,457 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

4.5

Excellent(498 Reviews)

Apartment

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 Apartment, 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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4.1

Excellent(97 Reviews)

Resort

in Orlando

Summerville Vacation Resort

Pool · Pets allowed · Kitchen / Kitchenette

Looking for a Resort in Osceola County, this Resort for $167 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

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4.7

Outstanding(444 Reviews)

Apartment

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 Apartment, for $114 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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4.0

Good(5,071 Reviews)

Hotel

in Orlando

Grand Hotel Kissimmee at Celebration - Shuttle to Theme Parks

Pool · Kitchen / Kitchenette · Air conditioner

Most favorited

Looking for the perfect place to call home during your trip to Osceola County? This Hotel offers a comfort and style with top-notch amenities, including Air conditioner, Fireplace 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

5.0

Outstanding(305 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 $354 per night for your next great vacation.

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3.1

Average(1,676 Reviews)

Inn

in Davenport

Rodeway Inn Davenport-Champions Gate

Pool · Pets allowed · Kitchen / Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Osceola County at Rodeway Inn Davenport-Champions Gate for $59 for your next trip.

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4.3

Excellent(1,867 Reviews)

Hotel

in Orlando

3star

Comfort Suites Maingate East

Pool · Kitchen / 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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3.5

Average(6,528 Reviews)

Hotel

in Orlando

3star

Ramada by Wyndham Kissimmee Gateway - Free Theme Park Shuttle

Garden · Pool · Pets allowed

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Osceola County, at $170 per night for your next great vacation.

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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.