Monthly Rentals in Old Town

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

Nearby monthly rentals

Superhost
Home in Woodlands
4.9 out of 5 average rating, 10 reviews

Family Beachside Living with Oceanviews & Pool

IanRating, 5 stars4 months ago
Great location on island, essentially within 20 minutes’ drive of all places of interest/accessible points, yet serenely secluded and quiet (except for lapping surf!). 5 minute walk to the beautiful Woodlands Beach for bathing and snorkelling, often having site to one’s self. First class communication throughout with both owner and local agent, plus the most comprehensive local user guide we have ever received at an AirBnB. Light and airy open-plan living area with ocean views, leading to two separate outdoor dining areas on opposing aspects, one sheltered and one covered. Kitchen equipped with all utensils and appliances required for cooking elaborate meals. Local supermarkets only 10 min drive in either direction plus local food stalls for fresh produce. Although not air conditioned, this was never an issue with great ventilation/local climate and ceiling fans are provided too. Tastefully furnished with more than ample seating options. Large well-maintained swimming pool.
Guest favorite
Apartment in Davy Hill
5 out of 5 average rating, 31 reviews

Woodland Suite, Urban Retreat

JonathanRating, 5 stars1 week ago
Great little studio space, which is very clean and orderly, almost like a little hotel room - although nice that it’s not, since a bit more personable. It’s in a building with a few more rooms presumably similar, but I was the only one around during my stay. Nice little balcony, lovely breezes and well outfitted kitchen. This was a great place to arrive and settle into Montserrat. I also got to rent a car from Sharra which was a great a seamless experience. Will definitely keep this as a top option for my future stays in Montserrat. Thank you Sharra!
Guesthouse in Salem
5 out of 5 average rating, 3 reviews

Hibiscus Suite - Private 1 Bed

TaraRating, 5 stars3 months ago
Lovely view , nice clean rooms peaceful n very comfortable
Guest favorite
Villa in Woodlands
4.94 out of 5 average rating, 17 reviews

Oceanfront luxury, king bed,AC,WiFi,4beds,3bedroom

SerenaRating, 5 stars1 month ago
We had an incredible stay at David's villa for a surprise birthday weekend for my 10-year-old daughter, Alexia. From the moment we arrived, David and his team went above and beyond to make it a memorable celebration. They organized a surprise birthday party that included beautiful decorations in Alexia’s favorite colors, a delicious birthday cake, tasty food, and fun games — everything was tastefully done and truly special. They even invited a few of the team's kids as party guests, which made the day even more unforgettable. Throughout our stay, David arranged for a private chef and a housekeeper, and both exceeded our expectations. The food was outstanding, and the housekeeper surprised us by doing our laundry, adding a level of care and convenience that we greatly appreciated. The house itself is fantastic — equipped with a great pool, surrounded by peaceful scenery, and offering the service of a five-star hotel. We felt completely relaxed and pampered the entire time.

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.

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