Monthly Rentals in Wailea-Makena

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

Nearby monthly rentals

Top guest favourite

A scenic view of the beachfront property showcases lush green lawns and swaying palm trees near the ocean. The sandy beach lies just beyond the rocky shore, inviting guests to enjoy the coastal beauty and tranquility of the Wailea Elua Village.

Apartment in Kihei

5 out of 5 average rating, 80 reviews

Luxe 2bed Wailea, 5-min walk to beach, ocean view,

Superhost

An outdoor dining area is shown with a large table surrounded by cushioned chairs, overlooking a vibrant ocean view. A patio umbrella provides shade, and the blue sky features scattered clouds, while palm trees frame the scene, enhancing the coastal atmosphere.

Apartment in Kihei

5 out of 5 average rating, 8 reviews

Oceanfront Condo with Spectacular Views! MSF201

Guest favourite

A bright, open living area features modern furnishings including a spacious sofa and lounge chairs. Large sliding glass doors provide views of the garden and ocean, while a ceiling fan enhances airflow. A round coffee table sits on a woven rug, complementing the hardwood floors.

Flat in Wailea-Makena

4.95 out of 5 average rating, 110 reviews

A.R.A Retreats: Garden Oasis

Luxe

Apartment in Kihei

4.98 out of 5 average rating, 57 reviews

Wailea Ekolu #207 – Oceanview Luxury in the Heart

The comforts of home and great monthly rates

Fully furnished rentals

From peaceful mountain cabins to convenient urban apartments, these furnished rentals have all the amenities of home.

Digital nomads & travelling professionals

Comfortable accommodation for nomadic and remote working professionals with wifi and dedicated work spaces.

Delight included

Sometimes the destination is the accommodation. From cliffside cabins to tranquil houseboats, these rentals are full of unique features.

Pets welcome

Discover places to stay that accommodate pets so that you can bring your four-legged friend along.

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.

Popular amenities for monthly rentals

Kitchen

Wifi

Pet-friendly

Laptop-friendly workspace

Free parking on premises

Corporate Housing

Stay near Wailea's top sights

Kamaole Sands

3 locals recommend

Wailea Beach

81 locals recommend

Mana Kai Maui

12 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.