Monthly Rentals in Kaupo

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

Nearby monthly rentals

Guest favourite
Cottage in Hana
4.95 out of 5 average rating, 152 reviews

Solar Cottage With Privacy & Panoramic Ocean Views

RyanRating, 5 stars2 weeks ago
Absolutely loved our stay at this stunning cottage. Tucked away in a lush garden paradise, the setting was peaceful, private, and beyond picturesque. Waking up to ocean views every morning and falling asleep to the sound of overnight showers felt magical. The cottage itself was clean & cozy. We especially enjoyed sipping morning coffee on the deck while enjoying our ocean view. Wonderful place to call home while exploring the Hana side of the island, and our hosts were very friendly and welcoming. Highly recommend to anyone looking for a serene escape in a beautiful location. Would come back in a heartbeat!
Top guest favourite
Farm stay in Makawao
4.99 out of 5 average rating, 327 reviews

Maliko Retreat

IshitaRating, 5 stars6 days ago
Great home with breathtaking views and comfortable for a family vacation. This place is a little rustic but well maintained and very clean. There are critters so if you’re afraid of bugs and little lizards, this might not be the place for you. There are plenty of birds and of course chickens on the property which the kids love. We had a wonderful time staying here and hope we can come back soon.
Guest favourite
Bungalow in Hana
4.94 out of 5 average rating, 162 reviews

Romantic Hamoa Bay Bungalow

MichaellaRating, 5 stars3 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.
Superhost
Cottage in Hana
4.82 out of 5 average rating, 208 reviews

Hana Ocean Palms Bungalow STHA2009-003

UlaRating, 5 stars3 weeks ago
We truly enjoyed our 8-night stay at Albert’s place! The location is absolutely perfect—just a short walk to the stunning Venus Pool and close to Hamoa Beach. The house is surrounded by a beautifully landscaped yard that adds to the charm and tranquility of the property. One of our favorite features was the outdoor shower—everyone loved it so much that we barely used the indoor one! The house had everything we needed for a comfortable stay, including boogie boards, and Albert provided some fantastic suggestions that really enhanced our visit. If you’re looking for luxury accommodations, this may not be the spot for you. It’s a modest home, but it’s full of personality, warmth, and that special island vibe that makes it truly unforgettable.

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

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.
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