Discover a selection of more than 10,000 vacation rentals in Osceola County, US that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including private pools and swimming pools. Prices start at $119 per night, and houses and condos are popular options for a stay in Osceola County. Either way, you'll find a rental for everyone's needs.
AsyncDestinationUrgency
Top rated rentals — Osceola County
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncDestinationInfographic
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy
AsyncExploreBookEnjoy

What are the top vacation 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 vacation 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 Theater": 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 vacation rental for you.

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

You need only step inside one of Vrbo's tiny house vacation rentals in Osceola County to find out that amazing things really do come in little packages. Efficiently designed to maximize space, these mini digs promise a big vacation experience:

  • Get ready for a simpler way of living at "The Cottage - Quaint Tiny Home Filled With Charm". Amenities at this hideaway in Princeton - Silver Star include a kitchen, free toiletries and more.
  • Alternatively, book a weekend at "The Universal - Stylish Tiny Home Perfect For A Family Vacation". Situated in Princeton - Silver Star, this tiny gem comes with a garden and a toaster.

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 vacation 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 center 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 cozy, 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 favorite among many travelers.

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 vacation 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 Theater" 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 vacation 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 vacation rentals in Osceola County that cater to large groups, starting with these sprawling retreats:

  • "Theme Rooms, Splashpad, Movie Theater": 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 vacation rentals that sleep 30 or more in Osceola County?

If you're organizing 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 vacation 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.

Explore destinations around Osceola County

Windsor Hills
2,403 vacation rentals
Bellavida
840 vacation rentals
Cumbrian Lakes
137 vacation rentals
Lake Berkley
827 vacation rentals
Eagle Pointe South
360 vacation rentals
Historic Downtown Kissimmee
232 vacation rentals
Venetian Bay Villages
265 vacation rentals
Lindfields
2,193 vacation rentals
Sunset Lakes
4,180 vacation rentals
Veranda Palms
667 vacation rentals
Crystal Cove
706 vacation rentals
Indian Point
1,787 vacation rentals
Chatham Park
293 vacation rentals
Lakeside Estates
27 vacation rentals
Crescent Lakes
102 vacation rentals
Indian Wells
613 vacation rentals
Crestwynd Bay
1,772 vacation rentals
Bass Lakes Estates
711 vacation rentals
Trafalgar Village
35 vacation rentals
Indian Ridge
769 vacation rentals