Monthly Rentals in Wailea

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

Nearby monthly rentals

Top guest favorite
Home in Hakalau
5 out of 5 average rating, 15 reviews

Oceanfront "Treehouse" at Hakalau with Kitchen

GregoryRating, 5 stars1 week ago
My partner, Stacey, and I stayed six nights here. Photos and descriptions are accurate. The property management company was extremely responsive to questions (i.e. seconds). We enjoyed the private and quiet, cliff-top ocean-view location. The location is very beautiful. Stacey enjoyed meeting the home-owner, Alan, who was present in his adjacent residence for a few days. We appreciated the box of beach goodies: chairs, umbrellas, beach matts, boogie board, floats, frisbee, etc. Kitchen is well equipped, and even had ice packs for the soft cooler that we brought with us to Hawaii. There were some basic cooking supplies that other guests presumably left behind (i.e. tea, cooking oil, sugar cubes, salad dressing). There was no coffee, however. We contributed peanut butter to the stockpile. YMMV.
Top guest favorite
Farm stay in Honomu
4.98 out of 5 average rating, 42 reviews

Lychee Orchard Hideaway (NEW w/AC and Laundry)

ElizabethRating, 5 stars2 weeks ago
Sam & Maris’ Airbnb was wonderful. The place was surrounded by lychee trees and the sounds of birds. It fit comfortably my family of four. It was well equipped with amenities too. They even had fruit and wine for us upon arrival! I’d definitely stay there again.
Top guest favorite
Farm stay in Honomu
5 out of 5 average rating, 45 reviews

Luxury Farm House 3/3 King Queen 13 mile from Hilo

LingRating, 5 stars3 months ago
The place is immaculately clean, and the host, Jane, is exceptionally hospitable. She welcomed us with juicy and fresh star fruits, as well as a homemade banana walnut cake that was absolutely delicious. The view from the house is lovely—you can see the ocean from the master bedroom, and the surroundings are peaceful and serene. The house is fully equipped with everything you might need, and each room is spacious and features its own private bathroom. From the property, you can also enjoy a clear view of Mauna Kea. Our stay was truly enjoyable, and we cherished every moment there. Highly recommended!
Guest favorite
Guesthouse in Hakalau
4.93 out of 5 average rating, 214 reviews

Oceanfront Gated Estate Retreat - 2 with Horses

ChristyRating, 5 stars2 weeks ago
What a LOVELY ESCAPE☀️From the moment of reservation to the departure, top notch experience. Maggie was a joy, and our 3 night stay was not nearly enough to truly enjoy the beauty, VIEWS and attention to detail from your animals, FLOWERs and peaceful “spaces”. Hope to return and relax here ! Thank you for sharing the paradise you have shaped! Oh yeah- we stayed in the Solar Suite- which was amazing-So comfy and spacious, welcoming the bathroom :) !! Your personal touches and care can be felt throughout… even offering to keep peeps luggage when flights are later than departure. THE VIEWS can’t be described -right from the bed!- grateful💕💕💕💕

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