Monthly Rentals in Smith Island

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

Nearby monthly rentals

Guest favorite
Home in Smith Island
5 out of 5 average rating, 11 reviews

HH Ranch on Smith Island w/ Golf Cart

JonRating, 5 stars3 months ago
This house is truly a hidden gem on the island. It’s fully stocked and beautifully furnished, catering to all types of travelers—whether you’re an adventurer looking to explore or someone like me who enjoys relaxing at home. Everything you could possibly need is right here, making it perfect for a peaceful getaway or an unforgettable vacation. I absolutely loved my stay and can’t wait to return in the near future!
Top guest favorite
Home in Smith Island
4.89 out of 5 average rating, 72 reviews

Smith Island Yummy Artist Retreat

JenniferRating, 5 stars3 months ago
I had an incredible, incredible time at Jemma's place. She is a consummate hostess--she was responsive and welcoming even before I made the official decision to book (I sent her some queries before booking and she was so very helpful!) Once there, she was a lovely mix of warm and friendly, yet respectful of her guests' time and privacy. She even let me borrow her rain boots when I didn't pack any! I felt right at home at the house and on the island immediately... to the point that it was a little emotional leaving! I think it's worth noting (because I was concerned about this before my arrival myself, and some of the older reviews cast some doubt...): the internet at Jemma's is very fast and reliable! I depended on it for working remotely throughout my whole stay, and it never failed me throughout zoom meetings, webinar streams, etc. I would highly recommend this beautiful home to anyone!!
Guest favorite
Guest suite in Crisfield
4.75 out of 5 average rating, 199 reviews

The Serenity House

MaignanRating, 5 stars3 weeks ago
I had an amazing stay at Anna's place! the accommodation was exactly as described- clean, comfortable, and with everything I needed for a relaxing weekend Anna's was incredibly welcoming,responsive, and ensure everything was perfect for my stay I will definitely coming back when I'm in town again
Top guest favorite
Cottage in Smith Island
4.97 out of 5 average rating, 220 reviews

Levering Creek Cottage with Private Dock

CaitlynRating, 5 stars1 month ago
We needed a place to chill and unwind and this was it! Not much to do this time of year but we didn't care. We loved every minute of our time on the island. Everyone was so friendly and we felt right at home. Beautiful sunsets and delicious catered meals. Thank you!!!

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.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

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.