Vacation Rentals in Osceola County: 36,500+ properties

Top vacation rentals in Osceola County

4.1

Excellent(97 Reviews)

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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4.0

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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4.3

Excellent(1,101 Reviews)

Resort

in Kissimmee

Gaylord Palms Resort & Convention Center

Garden · Pool · Kitchen / Kitchenette

Are you ready to indulge in a relaxing getaway? Our Resort in Osceola County has everything you need for a rejuvenating stay. Treat yourself to Gaylord Palms Resort & Convention Center's exceptional amenities, such as Fireplace, Laundry and Balcony / Patio.

$$$$

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Apartment

in Florida

Midnight Blue & White

10 guests · 5 bedrooms · 4 baths

Pool · Family friendly

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

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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

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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4.2

Excellent(4,298 Reviews)

Hotel

in Kissimmee

3star

Red Lion Hotel Orlando Lake Buena Vista South

Garden · Pool · Air conditioner

Nestled in Osceola County, this Hotel is perfect for your next vacation. Enjoy Red Lion Hotel Orlando Lake Buena Vista South's top-rated amenities, including Air conditioner, Laundry and Balcony / Patio, 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.