Monthly Rentals in Wailea-Makena

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

Nearby monthly rentals

Guest favourite
Condo in Wailea
4.97 out of 5 average rating, 165 reviews

Wailea Gem-Remodeled Ocean View

MargaretRating, 5 stars1 month ago
The location can't be beat and the condo grounds are stunning. The patio gets beautiful sunset views. Comfortable bed & having a 2nd bathroom is really nice.
Guest favourite
Condo in Wailea
4.92 out of 5 average rating, 76 reviews

Wailea Elua 1101 - Beachfront Section - Ocean View

LisaRating, 5 stars2 weeks ago
Beautiful location and setting. Very well organized and equipped. Especially nice bathroom and kitchen. She was also very thoughtful on the smaller details too, such as hooks to hang towels, clothes line in tub, non scented cleaning products . Also Very nice setup on the lanai
Top guest favourite
Condo in Wailea-Makena
5 out of 5 average rating, 7 reviews

Luxurious Tropical Retreat with Oceanview

CraigRating, 5 stars2 days ago
This is hands down the nicest Airbnb property I have ever stayed at. In immaculate condition, the photos and description matched the property perfectly. In addition to the overall condition of the unit, it was appointed with basically every amenity you could think of - including a turkey roaster and a serving platter (perfect for a holiday stay)! If you have small children they have everything you would need. Heading to the beach and want to keep your drinks cool? Yep, they have an ice chest you can take. When I would reach out, Nancy and Alan were prompt in their responses - they were great hosts! I cannot say enough great things. We will definitely be back!
Top guest favourite
Condo in Kihei
5 out of 5 average rating, 139 reviews

Romantic, Luxury Condo with Spectacular Ocean View

DanielRating, 5 stars1 month ago
We had an amazing stay at Tony and Patty’s place! The sunsets from the lanai were absolutely stunning, and the location was perfect – everything we needed was either provided or just a short walk away. It truly felt like a home away from home. 10/10, and we can’t wait to come back!

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

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.

Stay near Wailea-Makena's top sights

Wailea Beach24 locals recommend
Kamaole Beach Park II30 locals recommend
Cafe O'Lei Kihei35 locals recommend
Monkeypod Kitchen by Merriman72 locals recommend
The Shops at Wailea36 locals recommend
Polo Beach9 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. United States
  3. Hawaii
  4. Maui County
  5. Wailea-Makena
  6. Monthly Rentals