Monthly Rentals in Highland Beach

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

Nearby monthly rentals

Guest favorite
Cottage in Edgewater
4.99 out of 5 average rating, 154 reviews

Waterfront Chesapeake Bay Sunrises w/Private PIER!

IsabelRating, 5 stars1 month ago
Heather’s place is a little paradise on the water. Peaceful, quiet, and perfect for some real rest and relaxation. The house was exactly as described—spotless, all new, and super comfortable inside, with beautiful outdoor spaces to enjoy. Annapolis is just a short 25-minute drive away if you’re looking for great food and things to do. Communication with Heather was easy and fast. I’d come back anytime I’m in the area again!
Guest favorite
Guesthouse in Annapolis
4.9 out of 5 average rating, 103 reviews

Private Cottage on gated estate

RoseRating, 5 stars1 month ago
We were in and out alot as were in Annapolis for a family baptism. The accommodations were wonderful. We had no problems.
Guest favorite
Guesthouse in Annapolis
4.9 out of 5 average rating, 280 reviews

Calico Cottage Guest House, king bed, free parking

LindsayRating, 5 stars1 day ago
Was such a nice and comfortable stay. Loved the outside areas that were available. Felt very homey and safe! Thank you also for the assorted teas I loved this as an avid tea drinker. Will be back for sure! Host was also very responsive and helpful.
Top guest favorite
Home in Annapolis
5 out of 5 average rating, 31 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

TolanRating, 5 stars1 week ago
We really enjoyed staying at this home. Such a beautiful view and extremely peaceful. Gwen was a great host. We would definitely stay here again.

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.