
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:28 Sept - 26 Oct
Image gallery for The Blue Tide House: Steps to Maui beaches + nearby eats

The Blue Tide House: Steps to Maui beaches + nearby eats
Kihei
Image gallery for Kihei Kai Nani 238 - Garden View 1 Bedroom, Split AC, Steps to Kamaole II Beach!

Kihei Kai Nani 238 - Garden View 1 Bedroom, Split AC, Steps to Kamaole II Beach!
Kihei
Image gallery for Ocean View Sunsets and Haleakala Sunrises! Resort Zoned!

Ocean View Sunsets and Haleakala Sunrises! Resort Zoned!
Kihei
Image gallery for PRICES SLASHED!! Partial Ocean View + Short Walk to Everywhere You Want to Go

PRICES SLASHED!! Partial Ocean View + Short Walk to Everywhere You Want to Go
Kihei
Image gallery for ~Amazing Ocean View on 3rd flr~ MAUI AWAITS YOU!!

~Amazing Ocean View on 3rd flr~ MAUI AWAITS YOU!!
Kihei
Image gallery for Great Wailea studio Condo

Great Wailea studio Condo
Kihei
Image gallery for 5 Star Ocean View, Beach House Chic, Click the Video tour below!

5 Star Ocean View, Beach House Chic, Click the Video tour below!
Kihei
Image gallery for Grand Champions 55, Beautifully Renovated Single Level, Ocean Views, Split AC

Grand Champions 55, Beautifully Renovated Single Level, Ocean Views, Split AC
Kihei
Image gallery for Relaxing Wailea Ekahi Garden Hideaway.

Relaxing Wailea Ekahi Garden Hideaway.
Kihei
Image gallery for Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!

Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!
Kihei
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 Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.

Wailea Sensation Vacation! Spectacular Oceanview Villa! On the 2nd hole.
Kihei
Image gallery for #162 Ground Floor Peak Ocean View New Stearns & Foster CA King Bed

#162 Ground Floor Peak Ocean View New Stearns & Foster CA King Bed
Kihei
Image gallery for Kamaole Sands 10-113: Ocean View, Ground Level, Renovated, Large Lanai, Split-AC

Kamaole Sands 10-113: Ocean View, Ground Level, Renovated, Large Lanai, Split-AC
Kihei
Image gallery for Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled

Luxury 3BR Wailea Kihei Retreat. Walk to Beaches, Private Lanai, Newly Remodeled
Kihei
Image gallery for Stunning Ocean View Wailea Beach Villa- Book & Save

Stunning Ocean View Wailea Beach Villa- Book & Save
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 Ekahi 27A: Priceless Ocean View from a Private Lanai

Ekahi 27A: Priceless Ocean View from a Private Lanai
Kihei
Image gallery for Kamaole Sands 4-407 - Ocean View, King Beds, Split-AC Pool, Hot Tubs - Book Now!

Kamaole Sands 4-407 - Ocean View, King Beds, Split-AC Pool, Hot Tubs - Book Now!
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 New! Palms 702 - Romantic Retreat - Split AC in Bedroom - Open-Air Living Area

New! Palms 702 - Romantic Retreat - Split AC in Bedroom - Open-Air Living Area
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 Budget Friendly - Kihei Akahi C-608, Ocean Views, Short Walk to Kamaole Beach II

Budget Friendly - Kihei Akahi C-608, Ocean Views, Short Walk to Kamaole Beach II
Kihei
Image gallery for Quiet, Private Paradise M208 steps to the tropical pool and tennis court

Quiet, Private Paradise M208 steps to the tropical pool and tennis court
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.