Winona vacation rentals

We found 49 vacation rentals — enter your dates for availability
Scroll through and select from vacation rentals in Winona to find one that's perfect for your trip. Whether you’re staying in a vacation home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include parking and a garden. Whatever you're looking for, you're sure to find a rental for everyone's needs, including a place that's non-smoking or offers accessibility.

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Winona

The natural setting of Winona is ready to explore

Learn about the unique charm of Winona with a stay in a private vacation home. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Winona

Are you looking for attractions to see while you're in the area? Venture out of your cozy vacation rental and check out everything that makes Winona a one-of-a-kind vacation spot. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Big Spring (18.6 mi / 29.9 km)
  • Echo Bluff State Park (21.2 mi / 34.2 km)
  • Rocky Falls (8.4 mi / 13.6 km)
  • Roy L. Beck Municipal Golf Course (10.2 mi / 16.4 km)

Exploring the natural landscape of Winona

Whether you're looking for exciting outdoor activities or just want to take in the scenery, Winona is a great place to get out in nature. These are a few of the area's most enchanting features, all within 30 miles (48.2 km) of the city center:

  • Big Spring (18.6 mi / 29.9 km)
  • Current River State Park (22.8 mi / 36.7 km)
  • Rocky Falls (8.4 mi / 13.6 km)
  • Cave Spring Park (16 mi / 25.8 km)
  • Round Spring Lower Beach (19.2 mi / 30.9 km)
  • Round Spring Cave (19.4 mi / 31.3 km)

Frequently asked questions

How much does it cost to rent a vacation rental in Winona?
The average price for a vacation home in Winona is based on several factors, like property type, season and length of stay. Whether you're in search of a villa with space for extended family or an apartment ideal for just you and the kids, just enter your dates of travel to find stays that offer great value.
How much does it cost to rent a beach house in Winona?
The average price for a vacation home by the beach in Winona depends on when you're traveling and the size and type of property you want. Find prices easily and quickly on Vrbo by entering your dates of travel. Then use the handy filter tool to choose the number of bedrooms and amenities essential to you, like air conditioning, a pool and WiFi.
What are popular rental amenities in Winona?
A water view, a nearby river and a barbecue grill head the list of most popular rental amenities in Winona. Whether you're heading away solo, with your sweetheart or a bunch of friends, Vrbo can help you find a vacation home that matches your style with all the extras you're looking for.
What are the top attractions for families in Winona?
Make plans for a family day out at Rocky Falls. This popular attraction is close to the heart of Winona.
How old do you have to be to rent a vacation rental in Winona?
The minimum age is generally 16, 18 or 21. It can change from property to property on Vrbo, so check the rules of your preferred Winona stay before you book.
How long can I rent a vacation rental in Winona for?
How long you can rent a vacation rental in Winona is up to the property. Simply enter your desired dates to view a list of options offering extended stays. With tons of creature comforts such as laundries and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to find the perfect place to call your home away from home in Winona.
Does Vrbo offer discounts for vacation homes in Winona?
In Winona, you'll find some fantastic discounts and bargains for weekly and monthly discounts on vacation rentals, as well as newly listed homes on Vrbo. Whether it's a short getaway or a few weeks away, we have a host of options to suit your needs and budget.

More Vacation Ideas