
Wailea-Makena long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Bookabach takes the hassle out of booking monthly rentals in Wailea-Makena. The wide selection available and useful search filters make finding your home away from home a breeze. Whether you’re looking for fast Wi-Fi for remote working, a fully equipped kitchen for home cooking or a pool where you can relax with a good book, you’re sure to find it on Bookabach. Many long-term rentals in Wailea-Makena are great for kids and welcome four-legged friends, too. What's more, some offer monthly discounts on extended-stay homes and weekly discounts on shorter-term rentals.
Featured long stay living spaces - Wailea-Makena
Showing deals for:9 Nov - 7 Dec
Image gallery for Koa Resort 2 Bed Ground Floor Condo -Air Conditioning

Koa Resort 2 Bed Ground Floor Condo -Air Conditioning
Kihei
Image gallery for Lauloa 410 - Top Floor, Oceanfront Lanai, Molokini & Halaeakala Views, Split A/C

Lauloa 410 - Top Floor, Oceanfront Lanai, Molokini & Halaeakala Views, Split A/C
Wailuku
Image gallery for Experience Oceanfront Luxury at Kanai A Nalu 209, a Spacious 2-Bd/2Ba Condo, AC!

Experience Oceanfront Luxury at Kanai A Nalu 209, a Spacious 2-Bd/2Ba Condo, AC!
Wailuku
Image gallery for Kanai a Nalu 314 - Modern, Renovated, Oceanfront Condo, Breathtaking Views, AC!

Kanai a Nalu 314 - Modern, Renovated, Oceanfront Condo, Breathtaking Views, AC!
Wailuku
Image gallery for Maui Kamaole G-202 - Spectacular Views, Updated and Elegant, Wi-Fi & Split-AC!

Maui Kamaole G-202 - Spectacular Views, Updated and Elegant, Wi-Fi & Split-AC!
Kihei
Image gallery for Island Surf 304 - Modern Renovation, Stunning Views, Dual Zone Split AC, Wi-Fi

Island Surf 304 - Modern Renovation, Stunning Views, Dual Zone Split AC, Wi-Fi
Kihei
Image gallery for Sugar Beach Resort Oceanfront Luxury Condo - Your new vacation home!

Sugar Beach Resort Oceanfront Luxury Condo - Your new vacation home!
Kihei
Image gallery for Haleakala Shores A-308 - Ocean/Mountain Views, Stylish 2br/2ba, Lanai, AC, Wi-Fi

Haleakala Shores A-308 - Ocean/Mountain Views, Stylish 2br/2ba, Lanai, AC, Wi-Fi
Kihei
Image gallery for Kamaole Sands 9-301 - Luxurious Renovation, Split AC, Wi-Fi, Ocean View Condo

Kamaole Sands 9-301 - Luxurious Renovation, Split AC, Wi-Fi, Ocean View Condo
Kihei
Image gallery for TROPICAL MAUI!!! Visit and stay in Comfort and Style...1b/2b

TROPICAL MAUI!!! Visit and stay in Comfort and Style...1b/2b
Kihei
Image gallery for Kamaole Sands 10-307, Ocean View, Large Lanai, Twin Murphy Beds, Split-AC, Wi-Fi

Kamaole Sands 10-307, Ocean View, Large Lanai, Twin Murphy Beds, Split-AC, Wi-Fi
Kihei
Image gallery for D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.

D211 Quiet & Private 2br2ba near Wailea 2026 Discount 10% 7 nts or more.
Kihei
Image gallery for Ocean View 1 Bed/1Bath Condo | AC | Pool | Full Kitchen in Kihei

Ocean View 1 Bed/1Bath Condo | AC | Pool | Full Kitchen in Kihei
Kihei
Image gallery for Experience Kamaole Sands 6-202, Stunning Renovation, Ocean View, Wi-Fi, Split AC

Experience Kamaole Sands 6-202, Stunning Renovation, Ocean View, Wi-Fi, Split AC
Kihei
Image gallery for Oceanview Top Floor Condo, with Internet Access.

Oceanview Top Floor Condo, with Internet Access.
Kihei
Image gallery for Kamaole Sands 4-411 - Stunning Modern Renovation, Enclosed Loft, 3 Zone Split-AC

Kamaole Sands 4-411 - Stunning Modern Renovation, Enclosed Loft, 3 Zone Split-AC
Kihei
Image gallery for Kamaole Sands 5-210 - Stunning 1BR/2BA, King Bed, Center-Cut Bldg 5, AC, Wi-Fi

Kamaole Sands 5-210 - Stunning 1BR/2BA, King Bed, Center-Cut Bldg 5, AC, Wi-Fi
Kihei
Image gallery for Tropical Centrally Located Ground Floor Kihei Condo Across from the Beach

Tropical Centrally Located Ground Floor Kihei Condo Across from the Beach
Kihei
Image gallery for Kamaole Sands 10-403 - Stunning Renovation - Penthouse Level - Split AC - Look!

Kamaole Sands 10-403 - Stunning Renovation - Penthouse Level - Split AC - Look!
Kihei
Image gallery for Updated 1BD/1BA in the best South Kihei location! (quiet split A/C + great WiFi)

Updated 1BD/1BA in the best South Kihei location! (quiet split A/C + great WiFi)
Kihei
Image gallery for Great Location! Steps to Best Beach!

Great Location! Steps to Best Beach!
Kihei
Image gallery for Haleakala Shores A-411 - Modern 2BR/2BA, 2 King Beds, Sleeps 4, Split AC, Wi-Fi

Haleakala Shores A-411 - Modern 2BR/2BA, 2 King Beds, Sleeps 4, Split AC, Wi-Fi
Kihei
Image gallery for Shores of Maui 215 - Dramatic Ocean Views, Steps to the Beach, Renovated, AC!

Shores of Maui 215 - Dramatic Ocean Views, Steps to the Beach, Renovated, AC!
Kihei
Image gallery for Hale Hui Kai 202 - Keawakapu Beach, Garden Views, Steps to the Beach, Split AC!

Hale Hui Kai 202 - Keawakapu Beach, Garden Views, Steps to the Beach, Split AC!
Kihei
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
Great discounts on monthly rentals in Wailea-Makena
You’ll often find discounted rates for long stays of over 28 days on Bookabach, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Bookabach, you'll enjoy secluded stays with entire monthly rental homes just for you.
Pet-friendly monthly rentals
Many homes welcome guests with animal companions, so you don’t have to leave your pet at home.
Wailea-Makena Furnished monthly rentals for remote workers
Find your perfect home office set up. There are plenty of stays on Bookabach with dedicated workspaces and fast Wi-Fi so that you can take your work with you.
Monthly stays with practical kitchens
Most furnished extended-stay rentals in Wailea-Makena come with well-equipped kitchens ideal for home cooking, so you can enjoy healthy meals in or even host your own dinner parties.
Long-term rentals with parking in Wailea-Makena
Take advantage of the ‘amenities’ filter to find monthly stays with their very own parking spot for the ultimate in convenience.
Wheelchair-accessible holiday rentals
Bookabach offers a range of monthly rental homes designed to accommodate everyone for a comfortable and inclusive extended stay.
Holiday rentals in Wailea-Makena with pool
Bookabach's handy search filters will help you find monthly holiday homes with swimming pools so that you can relax in your very own pool.
Rentals with free cancellation in Wailea-Makena
Plans change. We get that. With Bookabach, you can search, select 'free cancellation,' and see all rentals in Wailea-Makena with flexible cancellation policies.