Monthly Rentals in Wailea

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

Nearby monthly rentals

Top guest favourite
Farm stay in Honomu
4.98 out of 5 average rating, 47 reviews

Lychee Orchard Hideaway (NEW w/AC and Laundry)

SarahRating, 5 stars6 days 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 favourite
Farm stay in Hakalau
4.95 out of 5 average rating, 391 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 favourite
Flat in Pepeekeo
5 out of 5 average rating, 19 reviews

Cozy 2BR/2BA Haven near Botanical World Adventures

NatalieRating, 5 stars6 days ago
Pictures cannot do the place justice! The back yard is gorgeous, right on the water, and has plenty of spots to sit and chill, rain or shine. The living area and kitchenette are spacious - we were able to cook everything we needed for 6 days, the couch is like a cloud, good wifi. Linens, towels, bathrooms, everything was pristine. Plenty of beach towels in the unit and great beach/water equipment for general use. Everywhere we wanted to go already required a car so it was totally worth being a little outside Hilo to get the scenery, with grocery store and shops about 20 min away. Denise and Matt responded to messages right away and there was someone on the property who helped us check in.
Guest favourite
Guest house in Hakalau
4.93 out of 5 average rating, 221 reviews

Oceanfront Gated Estate Retreat - 2 with Horses

CieraRating, 5 stars3 weeks ago
The solar room was nothing short of amazing. The property is beautiful and the views almost don't look real. The apartment was spotless, spacious, and so lovely. We loved waking up the crashing waves and had breakfast each morning right outside the room. The shower was really nice and the kitchenette was perfect for our stay. This place is absolutely worth it and should we find ourselves back on the Big Island, we would absolutely stay 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.
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