Monthly Rentals in Wailea

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

Nearby monthly rentals

Top guest favorite
Home in Hakalau
5 out of 5 average rating, 22 reviews

Oceanfront "Treehouse" at Hakalau with Kitchen

DaynnaRating, 5 stars1 week ago
This place was a slice of heaven on earth! Nicely furnished, nicely stocked kitchen and very comfy beds; but spent much of the time outside. The yard is a cornucopia of beauty, with flowering trees, sweet smelling shrubs and a million dollar view. My advice would be to splurge and get the place on the ocean, it is more than worth it! Watching the sun rise while sitting on the porch with my coffee was priceless. Close enough to Hilo and waterfalls, but the neighborhood is secluded and feels like a private retreat. The house that shares the property was vacant while we were there, but don’t think there would have been issues if it would have been occupied. We would definitely rent this place again if we are lucky enough to come back!!
Top guest favorite
Farm stay in Honomu
4.98 out of 5 average rating, 47 reviews

Lychee Orchard Hideaway (NEW w/AC and Laundry)

SarahRating, 5 stars1 week ago
This was probably our favorite Airbnb ever! We especially enjoyed the little details like a bottle of wine, lychee, cold water, delicious juice, guest book, and laundry detergent. They thought of everything to make us feel welcome! Thank you for a wonderful stay. Lychee is our new favorite fruit <3
Guest favorite
Farm stay in Hakalau
4.95 out of 5 average rating, 392 reviews

Forest Hale Cabin @ Permaculture Farm, Waterfall

HuitingRating, 5 stars2 weeks ago
Lovely place! It’s deep in the woods so it’s perfect for us as it’s quiet and away from noise and the crowds. The last ~0.2 mile was a bit rough, but we managed it with a mustang lol. What I enjoyed the most was sitting outside when it was raining. Enjoying the orchestra from nature.
Top guest favorite
Guesthouse in Hakalau
4.82 out of 5 average rating, 61 reviews

Royal Palm Cottage

JuyeunRating, 5 stars1 month ago
Palm tree cottage was such a gem! It’s surrounded by beautiful palm trees and peaceful nature sounds, aa described. The place was super clean and cozy, and we loved the welcome tray with fresh fruit and yummy banana bread. Laurel was really responsive and easy to communicate with. We’re so glad we found this place — it made our Hawaii trip even better!

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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