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
4.92 out of 5 average rating, 96 reviews

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

JenniferRating, 5 stars2 weeks ago
5+ stars for this airy, comfortable, sparkling clean space. I loved everything about Sidney’s place: it has a super relaxing vibe, comfortable bed, and that view! The unit is well-appointed with many thoughtful touches worthy of the “superhost” designation. Additionally, the grounds are absolutely gorgeous with a perfect resort style pool. Sidney’s communication was on-point: quick, courteous and super helpful. I cannot wait to return to my new favorite condo on Maui.
Top guest favorite
Condo in Kihei
5 out of 5 average rating, 55 reviews

Ohe'o || Wailea Ekahi Unit 28B || Lowered Rates

KathleenRating, 5 stars1 month ago
One of the best Airbnb’s we’ve stayed in. Peaceful, quiet, serene. Short walk to the beach (after visiting 4 beaches on the south shore we decided the one in front of the condo was our favorite). Sat out on the lanai each morning, sipping coffee while watching Maui wake up. And the view was great - green grass, pool and ocean. Would definitely stay at Jazlyn’s place again.
Guest favorite
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
Guest favorite
Condo in Wailea-Makena
5 out of 5 average rating, 5 reviews

Luxurious Tropical Retreat with Oceanview

BrandonRating, 5 stars1 week ago
Beautiful property for our three night stay in Maui. Nancy was a great communicator, friendly and very informative. The place was pristine and had everything one could want while on an island vacation. Additionally, the propriety was very walkable to a lot of great restaurants, shopping and coffee. I highly recommend this property and will look to stay here again on our next visit. Thanks very much Nancy!

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

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.

Stay near Wailea, 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. Wailea
  7. Monthly Rentals