Search Vacation Homes in Osceola

Change your mind

Book hotels with free cancellation

Treat yourself

Be picky

Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Vacation Homes in Osceola

"We had an awesome stay! Great layout and beautiful outdoor areas."

"beautiful property and great stay for 4 families with kids. Very friendly and helpful host!"

SAR 2,763 total

includes taxes & fees

30 Sep - 1 Oct

"It was a wonderful place to stay for the weekend. So much space, activities and accommodations! We would certainly book this place again! "

"Beautiful property with great touches throughout! Very welcoming and comfortable for our stay! Would definitely stay here again the next time I am visiting Stillwater!"

SAR 1,266 total

includes taxes & fees

30 Sep - 1 Oct

"Great property! Enough space for larger group. "

"Everything was wonderful "

"Very nice house to stay in. Clean, comfortable and close to main street!Would definitely stay again!"

"This place was nice because it was quite . Lake life is very nice. "

"We stayed here based on the terrific location to Willow State Park. The property is gorgeous and you have so many areas to hike and explore including down to a really great stream. The owners were very attentive and they communicated well. Highly recommend this property!"

"Great house on a great location."

"The house is beautiful and the location is just 4 or so blocks from downtown which was perfect. We had a girls weekend here and everyone had a great time. The porches are lovely spots to enjoy the river views!"

"We had a great time."

"We were in Stillwater for a family wedding and the house was perfect for us. It is a 5 minute drive from the downtown area and the stores we needed were easy to get to. We really enjoyed our stay."

SAR 2,683 total

includes taxes & fees

30 Oct - 31 Oct

"This charming property was perfect for our group of six celebrating my wife’s and her best friend’s 50th birthdays. The location was perfect as it was easily walkable to the magnificent downtown Stillwater."

"Beautiful property that was perfect for my family. Would absolutely stay there again!"

"Great location. Great host."

"The Place was perfect, beautiful better than the pictures. "

"Beautiful home! Well kept, great amenities. Great for my family, kids enjoyed it. Would come back here again."

"This was an amazing property for our large family to gather together to celebrate Christmas. There was plenty of sleeping, dining and gathering space."

"We are return guests. The cabin was clean, comfortable and in a beautiful location! The king bed is fantastic.We look forward to our next stay. Thank you Mary Beth."

View all properties