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Osceola Vacation Rentals & Execstays Homes

About Osceola Vacation Rentals

There are more than 38 vacation rentals that are available in Osceola. These rentals, including vacation rentals, Execstays Homes (Execstays) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an Execstays property in Osceola.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Execstays Osceola, you have the flexibility of comparing different options of various deals with a single click. Looking for an Execstays with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by Execstays, and other popular Airbnb-style properties in Osceola. Places to stay near Osceola are 1661.13 ftยฒ on average, with prices averaging $405 a night.

Execstays makes it easy and safe to find and compare vacation rentals in Osceola with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

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Top Rental Accommodation Types in Osceola

Type Count
Vacation Homes 16
Holiday Apartments 4
Cottages 2

Use these Quick Filters to Find a Vacation Rental in Osceola

โ˜… Pro Tip: Execstays makes it easy to compare the best listings on Execstays homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Execstays homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Osceola.

Weather in Osceola, WI

View the weather forecast for Osceola before booking your Osceola Vacation Rentals to confirm your best time to go.

December - February
High 60ยฐF       Low 26ยฐF
March - May
High 77ยฐF       Low 40ยฐF
June - August
High 91ยฐF       Low 64ยฐF
September - November
High 84ยฐF       Low 38ยฐF

Top Attractions Around Osceola, WI

ExecStays offers a large selection of top attractions around Osceola. Research things to do on your vacation before you visit Osceola.


Riverwood Canoe
Osceola & St. Croix Valley Railway
St. Croix Casino Turtle Lake
Maplewood Mall
Wild Mountain
Ice Castle
Trollhaugen
St Croix National Scenic Riverway
WineHaven Winery and Vineyard
Somerset Amphitheater
Interstate State Park
Dancing Dragonfly Winery
Oneka Ridge Golf Course
Saint Croix Vineyards
William O'Brien State Park
New Richmond Golf Club
Running Aces Harness Park
Chateau St Croix Winery & Vineyard
Luck Golf Course
Century College

Other Places to Stay in Osceola, WI


Osceola & St. Croix Valley Railway 176 Properties
Riverwood Canoe 172 Properties
Nye 33 Properties

Frequently Asked Questions About Osceola?

What are the top hotels and resorts Osceola?

There are a lot of options in Osceola. If you plan on staying in the Osceola area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Osceola:

Which vacation homes in Osceola are best for families?

If you are looking for a family-friendly vacation home in Osceola, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Osceola:

How many Execstays vacation rentals are available in Osceola?

Currently, the total number of properties listed by Execstays in 2025 is over 38 in the Osceola area, and still counting. By aggregating listings from multiple websites, Execstays offers an immense amount of choice of the best Execstays properties in Osceola.โ€ฏ


People Also Ask

There are 38 Osceola, WI Vacation Rentals

Recently Booked Vacation Rentals in Osceola