Monthly Rentals in Wailea, Wailea-Makena

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

Nearby monthly rentals

Guest favorite
Condo in Wailea-Makena
5 out of 5 average rating, 7 reviews

Tropical Escape to Wailea with Stunning Oceanview

RuslanRating, 5 stars2 weeks ago
The room was excellent and clean. Easy to parking lot on guests only. A such beautiful view the ocean from balcony and room. The bedroom is clean and soft. :)
Guest favorite
Condo in Wailea-Makena
4.92 out of 5 average rating, 101 reviews

Luxury Condo w/wide Ocean View (Palms at Wailea)!

Paul Rating, 5 stars2 weeks ago
Our stay at Palms Wailea Unit #1502 was great! The communication, before, during, and after was much appreciated and helped make our stay so much more comfortable and enjoyable. The unit was nicely decorated and having the extra bathroom was super helpful. The views from the lanai, living room and bedroom were beautiful. Thanks for being such an accommodating host Sidney. Appreciate your kind helpful assistance with everything. We are looking forward to a return stay.
Guest favorite
Condo in Wailea
4.96 out of 5 average rating, 168 reviews

Wailea Gem-Remodeled Ocean View

NikolayRating, 5 stars2 weeks ago
Mostly good impression. Minor nit picks: TV could be larger and newer for that price. The air conditioning on the balcony from the upstairs was noisy (and in general, the unit ACs are imho on the older side of the scale) until a miracle happened and new guests above finally turned it off and then it was really quiet for the night. There was some loud construction at the neighbors on one of the days, but again, it was only for a day. Overall a good private place.
Top guest favorite
Condo in Kihei
5 out of 5 average rating, 143 reviews

Romantic, Luxury Condo with Spectacular Ocean View

HollyRating, 5 stars1 week ago
Wonderful Condo. Gorgeous views, exceptional location and extra gracious hosts. They did everything to make is feel welcome including coffee and a generous amount of supplies. The location is truly extraordinary and the hosts could not have been kinder. We'd love to return!!

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.*

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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.

Destinations to explore

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  2. United States
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  4. Maui County
  5. Wailea-Makena
  6. Wailea
  7. Monthly Rentals