44965+ Luxury Vacation Rentals & Cabins in Osceola County |
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Osceola County Cabin Rentals

About Osceola County Vacation Rentals

There are more than 44965 incredible getaway rentals that are available in Osceola County. These choices include cabins, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Stay Close to Nature with Cabinns.com and uncover great stays in Osceola County.

Cabinns.com features numerous last-minute deals on private villas, hotels, and cabin rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With Cabinns.com in Osceola County, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the Cabinns.com vacation rentals, resorts, and Airbnb-style properties in Osceola County. Places to stay near Osceola County are 1732.05 ft² on average, with prices averaging US $393 a night.

Cabinns.com helps you find the ideal holiday rental to create a lifetime of travel memories in Osceola County. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect cabin retreat today.

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Top Cabin Rentals, Cottages, and Holiday Home Rentals in Osceola County

Type Count
Vacation Homes 28050
Villas 7031
Holiday Apartments 3997
Cottages 406
Others 28
Ski Chalet Rentals 24
B&B 11
Cabin Rentals 11
Unique Vacation Rentals 4
Unique Vacation Rentals 1

Use these Quick Filters to Find a Vacation Rental in Osceola County

★ Pro Tip: Cabinns.com is a cabin vacation rental website, pulling some of the top cabins, luxury resorts, and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible cabin resorts and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in Osceola County with Cabinns.com.

Weather in Osceola County, FL

View the weather forecast for Osceola County before booking your Osceola County Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Activities Osceola County Guest Reviews Local Attractions

Cabins Provides a Large Selection of Cabins and Vacation Rentals in and Near Osceola County. Discover Top Attractions For Your Next Outdoor Adventure.


Old Town
ESPN Wide World of Sports
Osceola Heritage Park
Silver Spurs Arena
Kissimmee Lakefront Park
Mystic Dunes Golf Club
Medieval Times
ChampionsGate Golf Club
Fun Spot America
Reunion Resort Golf Course
Lake Tohopekaliga
Give Kids the World Village
192 Flea Market
Braves Spring Training
Osceola Performing Arts Center
Kissimmee Civic Center
Boggy Creek Airboat Rides
Capone's Dinner Show
Osceola Regional Medical Center
Austin-Tindall Regional Park
Skate Reflections
Falcon's Fire Golf Club
Celebration Golf Club
Kissimmee Go-Karts
Houston Astros Spring Training
Alligator Lake
Kissimmee Bay Country Club
Tupperware Center
Disney Wilderness Preserve
Congo River Golf

Find Nearby Cabin Rentals in these Cities & Neighborhoods


Kissimmee 27,836 Properties
Disney's Maingate West 19,868 Properties
Four Corners 18,982 Properties
West Kissimmee 16,764 Properties
Historic Downtown Kissimmee 8,099 Properties
Reunion 2,231 Properties
Windsor Hills 1,639 Properties
Disney's Maingate East 1,219 Properties
Windsor Palms 876 Properties
Bellavida 260 Properties
Lake Berkley 172 Properties
Buena Ventura Lakes 116 Properties

Complexes around Osceola County, FL


Kissimmee 310 Properties
Disney 40 Properties
Orlandos Sunshine Orlando 97 Properties
Corners 50 Properties
Paradise Townhome 26 Properties
Emerald Island Resort 46 Properties
Umco Clermont 30 Properties
Kissimmee 33 Properties
Garden 32 Properties
Solara Resort 10 Properties
Bella Vida Resort 10 Properties
Paradox Circle 16 Properties
Villa Bbq Grill 14 Properties
Seasons 10 Properties
Compass Bay 11 Properties
See More Complexes

Frequently Asked Questions About Osceola County?

What are the top cabins, lake houses & summer homes in Osceola County?

We provide an array of great vacation destinations in Osceola County. If you are looking to stay in or around the Osceola County area, make sure to browse our options to find a premium cabin resort or rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in Osceola County:

How many cabin rentals and resorts have private pools in Osceola County?

We have 21180 cabins, luxury resorts, and holiday home rentals featuring a private pool in and near Osceola County. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which cabin rental, resort, or holiday home in Osceola County is best for families?

Searching for a family-friendly cabin in Osceola County? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfectly fit families of all sizes.

How many hotels, resorts, or cabin rentals are available in Osceola County?

Cabinns.com offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by Cabinns.com in 2026 is over 44965 in the Osceola County area, and that number rises every day. By combining listings from multiple websites and travel providers, Cabinns.com can provide you with a diverse amount of choices of the best luxury stays in Osceola County.


People Also Ask

There are 406 hotels in Osceola County 728 resorts, and 39089 rentals

Recently Booked Private Villas, Cabin Resorts, and Rentals Osceola County