Simi Winery Summer Rentals, Cottages & Cabins

Book a Place to Stay in Simi Winery for Your Summer Getaway

About Simi Winery Summer Rental on PickleTrip

PickleTrip™'s summer rentals in Simi Winery are perfect for your next summer getaway. We offer a wide range of properties to choose from, including homes with top-notch pickleball courts or nearby facilities, private pools, indoor/outdoor pools, hot tubs, WiFi, beach access, and more. Whether you're traveling with family, friends, or a group, we have a rental that will suit your needs.

Enjoy the perfect summer vacation in Simi Winery with PickleTrip™. Our summer rental homes are designed to provide you with maximum comfort and relaxation. Choose from a variety of properties, including condos, resorts, villas, bungalows, cozy cabins, RVs, and cottages. Stay and play pickleball when you travel with PickleTrip™.

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Frequently Asked Questions About Simi Winery Luxury Rentals

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

In 2025, PickleTrip offers 194 summer rentals in or around Simi Winery. Find unique home rentals for your summer holiday or a weekend getaway with family and friends.
The average price per night for a summer rental in Simi Winery is $715. Check the full list of summer accommodations in Simi Winery.
There are 194 summer rentals, cabins, cottages and properties that are available to rent. Book for your next trip with PickleTrip.

Yes, here are some popular summer holiday rentals in Simi Winery that have a private or indoor pool:

Check all holiday rentals with a pool in Simi Winery on PickleTrip.

Yes, We have 194 summer rental homes in Simi Winery and types of place to stay in Simi Winery include:

  • Vacation Homes: 194 available for rent
  • Villas: 194 Rentals available for rent
  • Holiday Apartments: 194 Rentals available for rent
  • Hotels with Suites: 194 Rentals available for book
Yes, of course! There are many luxury summer rental properties in Simi Winery. Use our search filter to discover all of our luxury summer accommodations with an indoor/outdoor pool. Sorting by price is another way to find the most and least expensive luxury summer rentals in Simi Winery.