Monthly Rentals in Kaupo

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

Nearby monthly rentals

Guest favorite
Home in Hana
4.9 out of 5 average rating, 21 reviews

Koali Ranch Cottage

RichRating, 5 stars1 month ago
This place is truly an amazing place with amazing hosts. From the easy entry and the thoughtful amenities this Airbnb has it all. The privacy is perfect and the place was super cozy and warm. Close to all the fun things the town has to offer. Thanks for sharing your spot with us, we hope to stay with you again soon.
Top guest favorite
Condo in Kihei
4.93 out of 5 average rating, 143 reviews

The Spirit of Aloha-1Bed/1Bath in Tropical Resort

JoyceRating, 5 stars1 week ago
Connie and Chris went out of their way to answer every question and request. They were extremely responsive and accommodating. The place was spotless and they had anticipated every need - they even provided reef-safe sunscreen in case we had forgotten ours. all the kitchen utensils were there. we did all our own cooking and didn't lack for anything. A super big closet was a plus! Previous reviews had mentioned a disagreeable property manager. That problem has been corrected. The new manager is kind and helpful. The property is immaculate and guests had a relaxing time. We had a friend who locked himself out of his car and the manager came to the rescue. Many thanks again! I wouldn't hesitate to recommend Connie and Chris' apartment for anyone who wants a great value,a comfortable, convenient and quiet location, and first rate service in Kihei.
Top guest favorite
Apartment in Kula
4.91 out of 5 average rating, 1,057 reviews

Kula Treat - Upcountry Maui with Hot Tub!

MequetteRating, 5 stars4 days ago
Pamela was very responsive and flexible to a late check in. The short tour was great and provided orientation and a couple little safety notes that was helpful. It’s was dark but she also told me a little about the geography of the island from the view of the balcony. Mahalo for the kind hospitality!
Guest favorite
Bungalow in Hana
4.94 out of 5 average rating, 162 reviews

Romantic Hamoa Bay Bungalow

MichaellaRating, 5 stars2 weeks ago
My only regret is not staying longer. The sounds of the ocean and rainforest were so peaceful and the outdoor shower and bathtub were amazing. We walked to Hamoa Bay which was a gem and loved the fresh tropical flower arrangements and the ocean view.

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 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.
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