Monthly Rentals in Makena Bay

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

Nearby monthly rentals

Guest favorite
Condo in Wailea
4.96 out of 5 average rating, 168 reviews

Wailea Gem-Remodeled Ocean View

NikolayRating, 5 stars2 weeks ago
Mostly good impression. Minor nit picks: TV could be larger and newer for that price. The air conditioning on the balcony from the upstairs was noisy (and in general, the unit ACs are imho on the older side of the scale) until a miracle happened and new guests above finally turned it off and then it was really quiet for the night. There was some loud construction at the neighbors on one of the days, but again, it was only for a day. Overall a good private place.
Guest favorite
Condo in Kihei
4.91 out of 5 average rating, 104 reviews

Ocean view in South Kihei

JamieRating, 5 stars4 weeks ago
We loved this place! We walked to the nearby beaches and restaurants and loved our morning coffee on the lanai. The view is so worth it. It was very clean and comfortable. We especially appreciated the beach gear (towels, chairs, umbrella) that was provided. We cooked breakfast most mornings and found the kitchen to be well stocked with pots/pans/utensils. However, you’ll need to bring your own oils, seasonings, etc. We did have a few issues out of Craig’s control, and he was helpful in finding solutions. I did panic when we had landed on Maui and I hadn't received the condo code yet. I reached out and he replied within about an hour. I later saw that he sometimes doesn't give out that info until the day of check in, so don't be alarmed. Overall, we loved our stay and can't wait to visit Maui again. Even with a few hiccups, this place was amazing and great to come back to after a day of adventuring.
Top guest favorite
Condo in Kihei
5 out of 5 average rating, 143 reviews

Romantic, Luxury Condo with Spectacular Ocean View

HollyRating, 5 stars1 week ago
Wonderful Condo. Gorgeous views, exceptional location and extra gracious hosts. They did everything to make is feel welcome including coffee and a generous amount of supplies. The location is truly extraordinary and the hosts could not have been kinder. We'd love to return!!
Top guest favorite
Guest suite in Kihei
4.99 out of 5 average rating, 113 reviews

Sweeping Panoramic Ocean Views - Private Ohana

AliciaRating, 5 stars3 days ago
We just spent the most incredible week at April and Bob’s Ohana in Maui — truly a dream come true. From the moment we arrived, we felt so welcomed and cared for. A thoughtful gift basket filled with local goodies greeted us, and it was clear from the start that no detail had been overlooked. The Ohana itself is spotless, beautifully decorated, and stocked with everything you could possibly need. The surrounding grounds are absolutely meticulous — lush, vibrant, and so peaceful. We loved watching Bob work on a new stone pathway during our stay; it was fun to see the progress and added to the charm of the property. April and Bob are the kindest, most gracious hosts. They’ve created something really special here — a place that feels like home while also offering the magic of a true Hawaiian getaway. The neighborhood is quiet and lovely, surrounded by lush scenery and filled with aloha spirit. We can’t thank them enough for sharing their piece of paradise with us. Mahalo!

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.*

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Work-friendly spaces for digital nomads

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