Monthly Rentals in Chocolate Hole

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

Nearby monthly rentals

Guest favourite
Flat in Cruz Bay
5 out of 5 average rating, 15 reviews

Secluded Apartment - just outside Cruz Bay

DanielRating, 5 stars1 month ago
Was a great place to stay for two people. Felt secluded out on the deck at night with all the plants and trees. The bed is extremely comfy and big. Very nice having ac at night and the full kitchen is great if you feel like cooking your own meal once and awhile. I’ll def be looking to stay here again in the future!
Superhost
Villa in Cruz Bay
4.89 out of 5 average rating, 19 reviews

BlueWater Vista - 4 Bed Pool Villa, Amazing Views

CatherineRating, 5 stars1 month ago
Spent a few days here for a group trip and it was perfect! The house is huge and has everything you need. Amazing views and the pool was perfect. No scary roads getting to the house from the ferry docks. Ari was so helpful with recommendations and quick to respond. We had a small water issue and he had it fixed immediately. Would highly recommend this place!
Top guest favourite
Flat in Cruz Bay
5 out of 5 average rating, 25 reviews

True Blessings St John

BrianRating, 5 stars1 month ago
True Blessings was exactly that. We felt right at home right away. Laurel was very responsive to our inquiries. Plenty of room, beautiful deck area, close to supermarkets, restaurants and beaches. Relaxing area just around the corner from the busy Cruz Bay Area.
Top guest favourite
Cottage in Cruz Bay
4.98 out of 5 average rating, 82 reviews

Sol~Azul Cozy Studio Cottage w/ Pool & Ocean View

JoyceRating, 5 stars3 weeks ago
Beautiful setting, comfortable, roomy, attractive cottage. Nice to have a full kitchen, bed was super comfortable, sitting TV area was comfortable, sun porch with table and chairs was a plus too. The deck and pool area is so pretty and peaceful. I spent a lot of time just floating in that pool! Met Holly briefly a few times and she is very helpful and pleasant. LOVED to sit on the front porch in the morning watch and the random chicken walking around. Easy, quick access to Cruz Bay and the northern beaches. HIGHLY RECOMMEND!

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 wifi and dedicated working spaces.

Looking for serviced apartments?

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.