509+ Ocean Pines Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Ocean Pines

Discover more than 509 holiday rentals in Ocean Pines. Rent By Owner holiday homes has everything you need to find a place to stay near Ocean Pines, MD.

Whether you are looking for luxury villas in Ocean Pines, 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. 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 Ocean Pines with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in Ocean Pines for families, large parties, or private owner accommodations for long or short trips. Ocean Pines Pet-friendly holiday rentals are available. Book your favorite vacation rentals in Ocean Pines with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

Show more
Show less

Ocean Pines Holiday Homes Frequently Asked Questions

There are many holiday rentals available in Ocean Pines; however, here are a few of the most popular holiday homes listed in Ocean Pines on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in Ocean Pines to find one that works for you.
Yes, there are 509 self-catering family homes and holiday rentals in Ocean Pines.
There are more than 509 luxury holiday homes in or near Ocean Pines, according to 2025 data from Rent By Owner. Consider these homes for your next holiday:
Yes, there are 509 pet friendly rentals that are available in Ocean Pines.