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
Guesthouse in Annapolis
4.9 out of 5 average rating, 102 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.
Top guest favorite
Home in Annapolis
5 out of 5 average rating, 30 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

PninaRating, 5 stars1 week ago
Gwen was one of the friendliest, most responsive, proactive hosts we’ve ever had. Fantastic place. Incredible views with your own private pier right on the Bay! Calm, peaceful, modern vibe in this well-appointed home. Everything was incredibly well organized/stocked. Best coffee and tea set up I’ve seen at an Airbnb. Huge, open kitchen and huge family room for relaxing as a group. Loved the swinging bench outside and the shaded cabana. Didn’t get to use the fire pit this time, but loved that there was one. Thank you, Gwen- we’ll definitely be back!
Superhost
Home in Annapolis
4.94 out of 5 average rating, 16 reviews

Waterfront Getaway - Dock UR Boat & Walk to Beach

MichelleRating, 5 stars4 days ago
Our family had an excellent visit over Easter. We had 4 adults and 5 children and the house was perfect for us. Amazing water views, spotless house, with great amenities and supplies. Was super helpful to have all towels and linens provided and a well stocked kitchen! The dock was great for kids to fish off and the beach was in close walking distance with a playground and other fun activities. The views were spectacular and location was about a 12 minute drive to beautiful downtown Annapolis. Highly recommend!
Guest favorite
Guest suite in Riva
4.93 out of 5 average rating, 14 reviews

Cozy one bedroom appt on the water

ChristelRating, 5 stars3 months ago
I had a lovely time at Zelda’s. Her home is beautiful and cosy and it’s really pleasant to be able to walk around and enjoy the river. This is definitely my go to place for the holidays.

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.