Monthly Rentals in Kaupo

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

Nearby monthly rentals

Top guest favourite
Cottage in Hana
4.95 out of 5 average rating, 153 reviews

Solar Cottage With Privacy & Panoramic Ocean Views

EugeneRating, 5 stars4 weeks ago
We had a wonderful time staying at Michael's and Terry's cottage. The setting was amazing, with a view of the ocean and having entire botanical gardens to ourselves. The cottage was in great condition and well-equipped. We really appreciated fresh eggs from their chickens and tomatoes from their garden that they left us. Having read that it was off the grid, I had concerns about electricity and hot water, but we had no issues with them. The internet worked very well too. There was an orange cat who was very friendly and stayed on the patio the entire time we were there. The only thing that was less than ideal was the mattress, which was too soft for me. Communicating with Terry and Michael and their guests who were house sitting for them was a pleasure! If you stay there, please follow their advise and get groceries ahead of time, since the place is really remote and almost all food stands nearby closed very early.
Top guest favourite
Guest house in Kula
4.98 out of 5 average rating, 216 reviews

Upcountry Alpaca, Llama, and Rabbit working farm

SimonRating, 5 stars3 days ago
We stayed at Christine’s place for five nights and had an amazing time. The apartment was great to directly feel like home and it’s located in a quiet area with a great view. We had the chance to see the Alpacas Asher, Cal & Gabriel every day on our way to get to the car since they were “mowing” the grass in that area. We travelled around Maui from here and everything was accessible within a maximum drive of ~1h. Christine was always responsive and allowed us to feed the Alpacas (Apple or Banana) and invited us to see other animals on the farm. Overall, we highly recommend Christine’s place and would always stay at her house the next time we visit Maui.
Top guest favourite
Flat in Kula
4.92 out of 5 average rating, 1,079 reviews

Kula Treat - Upcountry Maui with Hot Tub!

GabrielaRating, 5 stars4 days ago
Kula Treat was peaceful, quiet and featured beautiful views of Maui. We selected this home because of its proximity to Haleakala and in return got to experience a beautiful community in Maui for the first time. The home is as described, rustic and homey with a lovely host who has truly thought of everything. Pamela had beach towels available, beach chairs and other sweet gestures like fresh local flowers and produce available for us. It made our short visit easy.
Superhost
Bungalow in Hana
4.95 out of 5 average rating, 167 reviews

Romantic Hamoa Bay Bungalow

LaurynRating, 5 stars2 weeks ago
This place was the best place I’ve stayed at, incredibly beautiful, quiet and spacious, with lots of privacy. Shelly was also very nice and helpful! It’s a little pricy but worth every penny, would love to visit again.

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 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.
  1. Airbnb
  2. United States
  3. Hawaii
  4. Maui County
  5. Kaupo
  6. Monthly Rentals