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60+ Smith Island Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near Smith Island

Discover more than 60 holiday rentals in Smith Island. Rent By Owner holiday homes has everything you need to find a place to stay near Smith Island, MD.

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

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Frequently Asked Questions About Smith Island Holiday Rentals

There are a lot of options in Smith Island. If you plan on staying in the Smith Island 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 Smith Island:

There are many holiday rentals available in Smith Island; however, here are a few of the most popular holiday homes listed in Smith Island 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 Smith Island to find one that works for you.
Yes, there are 60 self-catering family homes and holiday rentals in Smith Island.
There are more than 60 luxury holiday homes in or near Smith Island, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: