Monthly Rentals in Gwynn Island

Discover long-term rentals that feel like home for stays of a month or longer.

Nearby monthly rentals

Guest favorite
Home in Gwynn
5 out of 5 average rating, 7 reviews

Still Waters Cottage

MichelleRating, 5 stars9 months ago
Great house to stay. Very clean. Golf cart is a must. Don't have to walk anywhere. We will stay here again or maybe his other house on the island. 😁
Guest favorite
Cottage in Gwynn's Island
4.9 out of 5 average rating, 29 reviews

Little Gray Beach House

BenjaminRating, 5 stars1 week ago
we had an excellent time at the little grey house. its cute and comfy and the view is to die for. please do yourselves a favor and watch the sunrise at least once its beautiful. theres not much on the island itself for food but there are plenty of places to find good food near by. I highly recommend the pizza at southwind pizza. was really good. I promise you will enjoy your stay at. Will hopefully beable to book again next time were down in the area!
Guest favorite
Home in Gwynn
4.97 out of 5 average rating, 78 reviews

‘The Sand Crab’- Beachfront Cottage, Kayaks, WiFi

AmalRating, 5 stars6 months ago
We had a wonderful time at The Sand Crab. It is perfect for young kids who are looking to enjoy the beach and water. The outside shower made it so easy for us to wash after the beach. The house is well equipped, and wonderfully decorated. We are grateful for Chris and his family for opening up their home for us to stay and enjoy a family vacation. For sure, we will be back!
Top guest favorite
Cabin in Deltaville
4.97 out of 5 average rating, 287 reviews

"The Little Red Cabin" aka The Galley

Melba AtkinsonRating, 5 starstoday
Crossrip Campground is a very special place. The location on the Chesapeake Bay is stunning and our cabin had the best view possible. Folks who come here return again and again because it is so special. Fishing and kayaking are great pass times or just looking at the bay. Our screened in porch on The Galley gave us a wonderful view of all the action on the Bay.

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term vacation rentals and a single monthly payment without additional charges.*

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Work-friendly spaces for digital nomads

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.
*Some exclusions may apply in certain geographies and for some properties.
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