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 stars1 week 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.
Superhost
Condo in Wailea-Makena
5 out of 5 average rating, 5 reviews

Luxurious Tropical Retreat with Oceanview

BrandonRating, 5 stars1 day 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!
Top guest favorite
Condo in Wailea-Makena
5 out of 5 average rating, 34 reviews

New Listing | Maui Oasis at The Grand Champions

KimberlyRating, 5 stars3 weeks ago
This is a perfect place to stay for one or two people. It's exactly as it appears in the photos and has really everything you need, from cooking utensils and pots and pans, to beach chairs and towels, to a great little lanai with a lovely sunset view! Easy to walk to a number of good restaurants and a quick drive (3 minutes) to the beach - or a nice walk! Matthew was SUPER responsive and I felt that I was always looked after in the way that a hotel front desk or concierge would support you. Practical, tidy, attractive and great service:-) 5 stars!
Top guest favorite
Guest suite in Kihei
4.99 out of 5 average rating, 110 reviews

Sweeping Panoramic Ocean Views - Private Ohana

JohnRating, 5 stars1 week ago
Please don’t hesitate to book , extremely well kept home . 5 minute car ride to beautiful beaches near by . The best part of our vacation are the unbelievable sunsets and views from Lanie . Thank you Bob & April

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 Beach35 locals recommend
Kamaole Beach Park II201 locals recommend
Cafe O'Lei Kihei241 locals recommend
Monkeypod Kitchen by Merriman240 locals recommend
The Shops at Wailea222 locals recommend
Polo Beach11 locals recommend

Destinations to explore

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