Monthly Rentals in Chocolate Hole

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

Nearby monthly rentals

Top guest favorite
Apartment in Cruz Bay
5 out of 5 average rating, 79 reviews

Esperance~Pool~New~National Park

KevinRating, 5 stars1 week ago
We had such an amazing time at Monic’s place. It was the perfect relaxing getaway. The view from the balcony overlooking the pool was so stunning The space was super clean, cozy, and had everything we needed. You can tell Monic really puts love into hosting, she was so helpful and responsive, and made us feel totally at home. Also, the location was great! There were so many good restaurants within a 10–15 minute drive. We tried a few different spots for dinner and every one of them was amazing. We left feeling so relaxed and recharged. Already talking about when we can come back. Highly, highly recommend if you’re looking for a peaceful spot with unforgettable view
Superhost
Condo in Cruz Bay
4.8 out of 5 average rating, 131 reviews

Sunset Villa Studio Condo at The Hills Saint John

KaileeRating, 5 stars1 day ago
I cannot say enough positive things about David and this place! We got onto the island and long story short we couldn’t stay where we originally booked. This posting was available, it was 7 PM and David not only confirmed my booking within <5 minutes, but he also made sure that the place was unlocked and ready for us. It was clean and so comfortable. The views were INCREDIBLE. absolutely breathtaking. When I return to St. John one day, this is the only place I will consider booking. Highly recommend.
Top guest favorite
Villa in Cruz Bay
5 out of 5 average rating, 124 reviews

BLUE VIEW VILLA - Bluest View - Brand New...

MichelleRating, 5 stars2 days ago
This was my family’s first time to St. John, and I’m so thrilled we stayed at the Blue View Villa! The view was the best, most stunning I’ve ever seen at a place we’ve gone!! The villa was immaculate, the bedroom was beautiful, and being surrounded by the ocean was beyond lovely. Tim met us at the ferry, brought us to pick up our rental, had us follow him to the villa, gave us a tour of the villa and walked us through how to use everything. He gave great recommendations and was super responsive to any questions/texts. We were comfortable instantly. How much we loved our trip to St. John was heavily influenced by our love of this special villa. While we were at the beaches during the day and out for dinner and shopping at night, having this as our anchor every morning, for our afternoon showers after the beach, and coming home after dinner to sleep here every night was exquisite. I would 100% want to return to the Blue View Villa!!
Top guest favorite
Home in Cruz Bay
4.98 out of 5 average rating, 50 reviews

Caribbean Cottage Near the Sea

EmilyRating, 5 stars3 weeks ago
My husband and I spent our honeymoon at St. John and choosing Ramona and Chris’s place was absolutely perfect. Chris met us when we got our rental car and led us to the Airbnb which was so kind and helpful. He gave us a ton of local recommendations and answered any questions we had throughout the week. The views are absolutely breathtaking and are hard to fully capture on their listing pictures! The AC worked wonderfully and the outdoor shower made things feel extra tropical! The place came with a few cat friends that we thoroughly enjoyed and the stairs were the perfect workout in the morning before the beach. We hope to come back to St. John in the near future and will most definitely be back here if it is just the two of us! Thanks for making our trip so memorable with a wonderful home for the week!!

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 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.