Monthly Rentals in Highland Beach

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

Nearby monthly rentals

Enter dates and number of guests to see the total trip price including additional fees and taxes, and rounded up to the nearest integer.

Guest favourite

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 favourite

Guesthouse in Annapolis

4.86 out of 5 average rating, 98 reviews

Chesapeake Bay Escape | Cozy Retreat

TracyRating, 5 stars6 days ago

Melanie was a great host and our stay was comfortable. The cottage was clean, cozy and all amenities provided. The beach is just a short walk from the cottage, and shopping and restaurants are plentiful. We enjoyed our stay and highly recommend. Thanks, Melanie!

Guest favourite

Guesthouse in Annapolis

4.9 out of 5 average rating, 281 reviews

Calico Cottage Guest House, king bed, free parking

LindsayRating, 5 stars4 days 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 favourite

Home in Annapolis

5 out of 5 average rating, 32 reviews

Peaceful Waterfront Home in Annapolis 3BR 2BA.

DianeRating, 5 stars1 week ago

We loved our stay here. It was a peaceful and beautiful respite! Sitting on the dock and around the fire pit were highlights!

Explore all

The comforts of home and great monthly rates

Fully furnished rentals

From peaceful mountain cabins to convenient urban apartments these furnished rentals have all the amenities of home.

Digital nomads & travelling professionals

Comfortable accommodation for nomadic and remote working professionals, with Wi-Fi and dedicated workspaces.

Delight included

Sometimes the destination is the accommodation. From cliffside cabins to tranquil houseboats, these rentals are full of unique features.

Pets welcome

Discover places to stay that accommodate pets, so you can bring your four-legged friend along.

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 holiday 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

Travelling professional? Find a long-term stay with high-speed Wi-Fi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.

Popular amenities for monthly rentals

Kitchen

Wi-Fi

Pet friendly

Laptop-friendly workspace

Free parking on premises

Corporate Housing

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.