Vacation Rentals in Osceola County: 37,100+ properties

Choose from 37,066 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(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 $490 per night for your next great vacation.

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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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4.0

Good(6,924 Reviews)

Hotel

in Kissimmee

4star

Magic Moment Resort and Kids Club

Garden · Pool · Kitchen / Kitchenette

This Hotel in Osceola County, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

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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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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 $200 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

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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 $202 per night.

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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.