Vacation Rentals in Osceola County: 37,200+ properties

Choose from 37,236 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 $23,222 per night. Our most popular vacation rental types near Osceola County are House and Hotel.

Top vacation rentals in Osceola County

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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4.3

Excellent(422 Reviews)

Resort

in Orlando

Magic Village Yards Trademark Collection by Wyndham

Garden · Pool · Kitchen / Kitchenette

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

$$$$

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4.4

Excellent(62 Reviews)

House

in Orlando

Kissimmee Area Pool Home

Pool · Kitchen / Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Osceola County? This House offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$

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4.7

Outstanding(430 Reviews)

Condo

in Kissimmee

FLASH SALE! 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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Search by amenity

Explore vacation rentals with the most popular amenities in Osceola County

Vacation rentals with air conditioning in Osceola County

4.5

Excellent(465 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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3.1

Average(2,698 Reviews)

Inn

in Orlando

Rodeway Inn Kissimmee Maingate West - Free Theme Park Shuttle

Pool · Pets allowed · Kitchen / Kitchenette

This attractive Inn in Osceola County, $330 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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4.2

Excellent(428 Reviews)

House

in Kissimmee

Berkley Lake Townhomes

Pool · Kitchen / Kitchenette · Air conditioner

Nestled in Osceola County, this House is perfect for your next vacation. Enjoy Berkley Lake Townhomes's top-rated amenities, including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$

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3.5

Average(6,528 Reviews)

Hotel

in Orlando

3star

Ramada by Wyndham Kissimmee Gateway

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.