Monthly Rentals in Wailea

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

Nearby monthly rentals

Enter dates and number of guests to see the total trip price including additional fees and taxes, and rounded up to the nearest integer.

Top Guest favourite
Guesthouse in Honomu
4.95 out of 5 average rating, 57 reviews

ILIOPUA Paradise found

LauraRating, 5 stars3 months ago
We had a wonderful time staying at Beverly’s guest house! Beverly and Gerry are great hosts. We loved visits from their friendly dogs, Zack and Tibbey, walking down to see the goats, chickens and cow and just exploring their 44 acres. The personal touches of fresh eggs, pancake fixings, snacks and chocolates were so thoughtful. Being able to pick lemons and oranges was also a plus! Surrounded by natural beauty of the property, views of the ocean and Mauna Kea made it truly feel like paradise!! It is the perfect place to unwind and relax. Thank you Beverly and Gerry for a marvelous week and can’t wait to come back for a longer stay!
Top Guest favourite
Farm stay in Honomu
4.98 out of 5 average rating, 48 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 favourite
Farm stay in Hakalau
4.95 out of 5 average rating, 393 reviews

Forest Hale Cabin @ Permaculture Farm, Waterfall

CameronRating, 5 stars2 weeks ago
Secluded and now-pristine location on a piece of land that is lovingly and meticulously cared for. We loved our stay here and would highly recommend to anyone on the fence. The constant sounds of the birds, frogs, and waterfall made us feel as though we were living in a time machine.
Guest favourite
Holiday home in Hakalau
4.91 out of 5 average rating, 45 reviews

Hulili Farm - Pineapple Cottage

KaraRating, 5 stars1 week ago
We can't rave enough about the Pineapple Cottage. It was beautiful, peaceful, and a great way to unwind after our super busy days exploring the East side of the island and VNP. My husband would have ate himself sick on Lychees if I let him. We made friends with geckos, the resident dogs, Lucy and Molly and of course the friendly neigbourhood duck, Frankie. Coffee in the mornings on the lanai was a dream and we slept soundly listening to the frogs every night. Thank you to Madeleine and her family - they were great hosts and brought us farm fresh eggs one day which were delicious. We want to come back and hope we are able to in the future!

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 Wi-Fi 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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