142+ Sherwood Beach Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Sherwood Beach

Discover more than 142 holiday rentals in Sherwood Beach. PickleTrip™ holiday homes has everything you need to find a place to stay near Sherwood Beach, HI.

Whether you are looking for luxury villas in Sherwood Beach, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place with private pickleball courts or nearby facilities. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to Sherwood Beach with a whole family or group, PickleTrip™ holiday accommodations can make your trip more memorable. We have plenty of places to stay in Sherwood Beach for families, large parties, or private owner accommodations for long or short trips. Pet-friendly holiday rentals are available as well. Book your favorite vacation rentals in Sherwood Beach with PickleTrip™. Stay and play pickleball when you travel.

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Frequently Asked Questions About Sherwood Beach Holiday Rentals

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

There are many holiday rentals available in Sherwood Beach; however, here are a few of the most popular holiday homes listed in Sherwood Beach on our website:
At PickleTrip most of our places to stay are perfect for families. Check out the complete list of holiday homes in Sherwood Beach to find one that works for you.
Yes, there are 142 self-catering family homes and holiday rentals in Sherwood Beach.
There are more than 142 luxury holiday homes in or near Sherwood Beach, according to 2025 data from PickleTrip. Consider these homes for your next holiday:
Yes, there are 142 pet friendly rentals that are available in Sherwood Beach.