Discover a selection of more than 10,000 holiday rentals in Osceola County, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo holiday homes have the best amenities for hanging out with the people that matter most, including pool and private pool. Prices start at £ 122 per night, and houses and villas are popular options for a stay in Osceola County. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Osceola County
Destination guide

Book a holiday rental for your Osceola County getaway

Learn about the unique charm of Osceola County with a stay in a holiday home rental. This city has something for everyone. Walt Disney World® Resort and Walt Disney World® area are just a couple of the must-see attractions. Whether you're planning a family holiday, a trip with friends or a romantic retreat, HomeAway has a great selection of holiday homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Things to do

Sightseeing in and around Osceola County

Are you looking for attractions to see during your stay? Venture out of your cosy holiday rental and experience everything that makes Osceola County a fun place to get away to. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Epcot® (10.2 mi / 16.4 km)
  • Disney's Hollywood Studios® (10.3 mi / 16.6 km)
  • Walt Disney World® Resort (11.4 mi / 18.4 km)
  • Disney's Animal Kingdom® Theme Park (12.1 mi / 19.5 km)
  • Universal Orlando Resort (13 mi / 21 km)
  • Universal Studios Florida (13.4 mi / 21.6 km)
Natural features

Exploring the natural features in Osceola County

Whether you're looking for fun outdoor activities or just want to appreciate the scenery, Osceola County is a great place to get outside. These are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city centre:

  • Kissimmee Lakefront Park (0.2 mi / 0.3 km)
  • Osceola Heritage Park (2.4 mi / 3.9 km)
  • Lake Bryan (7.5 mi / 12.1 km)
  • Austin-Tindall Regional Park (8.3 mi / 13.4 km)
  • Bill Frederick Park (15.1 mi / 24.3 km)
  • Northeast Regional Park (15.8 mi / 25.4 km)
How to get there

Transport to and around Osceola County

Fly into Kissimmee, FL (ISM-Kissimmee Gateway), the closest airport, located 1.8 mi (2.9 km) from the city centre.

If you'd rather travel by train, the main station serving the city is Kissimmee Station. Walk to nearby metro transport at Tupperware Station or Poinciana Station and easily see more of the city.

What are the top holiday rentals in Osceola County?

From high-end condos to rustic log cabins, Vrbo has properties to suit all sorts of tastes and budgets. Here are some of the top holiday rentals in Osceola County:

  • "Luxurious Family - 4bedroom - Privacy Fenced Pool Hot Tub": This Four Corners rental offers 4 bedrooms and is rated highly among visitors. Amenities such as a stovetop and free WiFi help make your stay comfortable.
  • "Theme Rooms, Splashpad, Movie Theatre": Settle in at this property in Orlando and take advantage of off-street parking options, towels and more. It has 7 bedrooms to accommodate your family and friends.

For even more great options, use the search bar at the top of the page to find the perfect Osceola County holiday rental for you.

What are the best tiny house holiday rentals in Osceola County?

Punching above its weight when it comes to character, a tiny house holiday rental in Osceola County offers a front-row seat to big adventure. Disconnect your devices and switch your focus to Mother Nature at one of these pint-sized escapes:

  • You can look forward to a simpler way of living at "The Cottage - Quaint Tiny Home Filled With Charm". Amenities at this getaway in Princeton - Silver Star include a barbecue grill, a garden and more.
  • "The Venice - Trendy Tiny Home With Panoramic Views Of Beautiful Lake Fairview" in Princeton - Silver Star is another highly rated pick. A fireplace and a kitchen will make your time here even more comfortable.

Can I find log cabins to rent in Osceola County?

Vrbo has some awesome log cabins for rent in and near Osceola County. Get the rustic cabin experience while staying in the middle of nature at one of these impressive properties:

  • "Sebring Florida Best Kept Secret "cracker Hammock Log Cabin" is the ideal combination of outdoor adventure and comfort. Make the most of handy amenities here including a games room and a smart TV.
  • You won't have to forego any modern comforts if you stay at "Ranchero Log Cabin' On 40 - Acre Farm In Sebring". This escape features a garden, a kitchen and more.

What are the top-rated holiday rentals for weekend getaways in Osceola County?

While long trips overseas are awesome, there's something undeniably lovely about escaping for a whirlwind weekend getaway. These rental properties in Osceola County are ideal for just that:

  • "Welcome To The Windsor Fantasy" - This rental in Four Corners features amenities designed to make your visit nice and comfy, such as a private pool and an oven. Its wonderful location also makes it a good base to get out and explore.
  • "Minutes To Disney5 - Starman" - This is another great choice with all the ingredients that make for a wonderful weekend away. You'll have access to a living room and tennis at this Windsor Palms rental property.

Can I find studio apartments for rent in Osceola County?

If you want something a little more personal than the usual hotel room, you'll love our studio apartments in Osceola County. Cook in your kitchenette, snooze on the lounge and feel totally at home. Here are some of our coziest digs:

  • Nap, eat, hang out with friends … Do it all from the compact yet well-designed single room space at "Large Private Carriage - House Retreat With Amazing Views". Located in Kissimmee, a free nearby fitness centre and a nearby laundromat are among its amenities.
  • Start your day with a hot coffee and a cooked breakfast at "At Sea" Condo 10 Minutes From Disney". This West Kissimmee retreat has all the essentials to make your stay cosy, including off-street parking options and shopping.

Can I find short term rentals in Osceola County?

With Vrbo's terrific range of short-term rentals in Osceola County, it's easy to find a place that's a perfect match. Whether you're after somewhere to relax on your own or to hang out with family and friends, these options are tough to beat:

  • Located close to the middle of Four Corners, "Welcome To The Windsor Fantasy" is a perfect place for a short-term stay. Use it as a base to get out and explore all the fascinating attractions in the area.
  • "Minutes To Disney5 - Starman" also rolls out the welcome mat for short-term guests. Spend a day or two at this property in Windsor Palms and find out why it's a favourite among many travellers.

What are the best romantic weekend getaways in Osceola County?

A romantic weekend getaway in Osceola County is a surefire way to reignite your passion. Light some fancy candles, take your honey by the hand and get set to let the sparks fly at one of these holiday rentals:

  • Bond as a couple at "Luxurious Family - 4bedroom - Privacy Fenced Pool Hot Tub". This Four Corners rental is custom-made for romance, offering amenities like beauty services and winery tours to help set the mood.
  • Another alluring option is "Theme Rooms, Splashpad, Movie Theatre" in Orlando. Enjoy amenities here including a swimming pool and shopping facilities, as well as each other's company.

What are the best large group holiday rentals in Osceola County?

If your idea of the perfect trip away is to bring along all your friends, you're going to need a whole bunch of space. Luckily, there are plenty of holiday rentals in Osceola County that cater to large groups, starting with these sprawling retreats:

  • "Theme Rooms, Splashpad, Movie Theatre": This popular retreat is a terrific choice for larger groups wanting to stay in Orlando. It has 7 bedrooms and amenities that include a garden and a swimming pool.
  • "Welcome To The Windsor Fantasy": You'll get your squad's stamp of approval at this option in Four Corners which features a swimming pool, a garden and more. It has 5 bedrooms that will easily accommodate all your guests.

Are there large holiday rentals that sleep 30 or more in Osceola County?

If you're organising a big family reunion or a special event like an anniversary in Osceola County, you won't have to worry about leaving anyone off your invite list. Vrbo has a range of large holiday rentals that'll fit as many people as you like. Here are some terrific examples:

  • "Championsgate, 9 Bed Luxury Exec Villa": With 9 bedrooms sleeping up to 30 people, there's enough space for everybody at this property in Champions Gate. Useful amenities here include a kitchen and a swimming pool.
  • "Mission To Space Mansion 14 Bedrooms 14. 5 Baths": Accommodating up to 40 guests and featuring great amenities including a kitchen and a swimming pool, this is another standout. It has 14 bedrooms and is located in Lakeside Estates.

What are the best houses for rent with a pool in Osceola County?

Get ready to take your pick and dive right in. Here are a few superb house rentals in Osceola County where life is better beside the pool:

  • Kids, aunts, uncles, parents — everyone will want to chill by the pool at "5 Stars House With Wifi, Game Room". Take the whole family on a trip to this Crystal Cove rental home which also comes with towels and a TV.
  • "Awesome Deals - Fantastic 5bedroom House" in Windsor Palms is another popular pick. There's plenty to love about this property besides its pool, such as a porch and coffee and tea making facilities.

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