Osceola County Holiday Rentals

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Top Holiday Rentals Destinations in Osceola County

Relax in this serene outdoor seating area overlooking the water, surrounded by a railing and offering a view of the building with large windows.

"Nice place to stay"

includes taxes & fees

3 Aug - 4 Aug

"Very nice Penthouse Suite at the top of the Central Emporium. Very clean and the perfect layout. The views are incredible!! Loved my stay. I’m from Michigan but grew up vacationing at Vacation Village with my family one week every summer for around 17 years. We would always come to Arnold’s Park to shop, dine and enjoy the rides. We’d always shop at the stores in the Central Emporium. A great return visit. Thank you for everything."

Relax on the deck with a clear view of the water, featuring a fire pit and comfortable seating.

"The place was awesome "

includes taxes & fees

21 July - 22 July

"This house was perfect for our family! It’s an easy walk to both pools and restaurants. Had a few questions and always got a quick response. I highly recommend and would stay again!!!"

Relax by the fire in a serene outdoor setting overlooking a calm body of water.

"Very nice place for a family to stay."

includes taxes & fees

7 Aug - 8 Aug

Relax in this stylish living room with a flat-screen TV, comfortable sofa, and cozy chair.

"Perfect for our needs, c lean, comfortable Check in was great, check out was great and we had no issues while there."

includes taxes & fees

28 July - 29 July

Experience serene views of a tranquil water body from the comfort of a boat.

Relax by the pool surrounded by comfortable lounge chairs and shaded areas.

"Great location with great restaurants and lots of attractions nearby! Awesome views of lake!"

Relax on the deck overlooking the calm water with a round table and four chairs.

"Host was helpful, responsive and kind. The view was wonderful and the cabin cosy. What more can you ask for?"

Enjoy a view of the water from this living area with a sofa, side table, and ceiling fan.

"Excellent place to stay. Beautiful view and very comfortable beds "

includes taxes & fees

21 July - 22 July

Relax by the pool surrounded by lounge chairs and umbrellas, with a view of the surrounding area from the adjacent building's balconies.

"Clean and modern condo with great view of the lake, easy access to amenities. "

includes taxes & fees

30 July - 31 July

Guests can walk along the pier to the dock area, where boats and covered structures await.

"We had an awesome weekend. The location was perfect for our family getaway; quiet, lake view, and plenty of space for our family of six. "

Explore the play area surrounding this multi-level structure with a central platform and red roof.

"Great experience and great location to all the action!"

includes taxes & fees

27 July - 28 July

Relax by the serene lake with a boat and two chairs on the dock, surrounded by trees.

"we had a great time on east okoboji. FYI there was plenty of room to park our truck and boat trailer side by side. Its a nice quite part of the lake to get away from the hustle and bustle....but close enough to search it out too."

Enjoy cooking in this well-equipped kitchen with stainless steel appliances, wooden cabinetry, and granite countertops.

Enjoy al fresco dining on this outdoor deck with a grill, perfect for cooking up a meal.

"Perfect home our 2nd time staying. Will be back again soon! "

Relax in a cozy living space with a covered patio and seating area.

"Great location, and beautiful property."

includes taxes & fees

13 July - 14 July

Swim and play in the central pool surrounded by lounge chairs and a kids' play area with a slide and climbing structure.

"Beautiful place!! Loved the open concept!! Exceptional view!! Loved the veranda! Great location!!"

includes taxes & fees

6 Aug - 7 Aug

Enjoy cooking in this well-equipped kitchen with a refrigerator, microwave, and oven, and a granite countertop.

"Location is Amazing... great sunsets!!! Wonderful place for a family getaway, super friendly neighbors."

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Find out more about Osceola County

Everything you need to know about Osceola County holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osceola County holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osceola County holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osceola County holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osceola County. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osceola County holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osceola County holiday rentals we have selected for you start as low as NZ$288 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osceola County rentals

At Expedia, we put the best Osceola County holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osceola County rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osceola County holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osceola County. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.