Vacation Rentals in Osceola County: 36,600+ properties

Choose from 36,587 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

3.2

Average(1,087 Reviews)

Hotel

in Orlando

3star

Comfort Inn & Suites Kissimmee by the Parks

Pool · Kitchen / Kitchenette · Air conditioner

Most favorited

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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4.0

Good(1,347 Reviews)

Resort

in Orlando

Delta Hotels by Marriott Orlando Celebration

Garden · Pool · Pets allowed

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

$$$$

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3.9

Good(1,212 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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4.7

Outstanding(444 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 $120 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

5.0

Outstanding(294 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 $426 per night for your next great vacation.

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4.5

Excellent(481 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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4.5

Excellent(4,640 Reviews)

Resort

in Orlando

Celebration Suites

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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4.5

Excellent(353 Reviews)

Hotel

in Waverly

2star

Holiday Inn Express Lake Wales North-Winter Haven, an IHG Hotel

Pool · Pets allowed · Kitchen / Kitchenette

Looking to create some memories in Osceola County? Look no further than our Hotel, Holiday Inn Express Lake Wales North-Winter Haven, an IHG Hotel. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$

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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.