
Wailea 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. 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 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
Image gallery for Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!

Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!
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 Fabulous Ocean Views from Front Row Condo!

Fabulous Ocean Views from Front Row Condo!
Kihei
Image gallery for LUXURIOUS Wailea BEACH Direct Ocean Front Property Wailea Ekahi 42A 1 Bed/2B

LUXURIOUS Wailea BEACH Direct Ocean Front Property Wailea Ekahi 42A 1 Bed/2B
Kihei
Image gallery for Great Wailea studio Condo

Great Wailea studio 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 Escape to Serenity – Oceanview 1 Bedroom 2 Bath at Wailea Ekahi 48-E, Sleeps 4

Escape to Serenity – Oceanview 1 Bedroom 2 Bath at Wailea Ekahi 48-E, Sleeps 4
Kihei
Image gallery for Wailea Ekahi 20J - Secluded Garden Oasis Surrounded by Trees & Tropical Blooms

Wailea Ekahi 20J - Secluded Garden Oasis Surrounded by Trees & Tropical Blooms
Kihei
Image gallery for Wailea Ekahi 45D - Ocean & Garden Views, Beautifully Renovated, Split AC, Wi-Fi!

Wailea Ekahi 45D - Ocean & Garden Views, Beautifully Renovated, Split AC, Wi-Fi!
Kihei
Image gallery for Relaxing Wailea Ekahi Garden Hideaway.

Relaxing Wailea Ekahi Garden Hideaway.
Kihei
Image gallery for Discover Wailea Ekahi 39E - Breathtaking Ocean Views, Renovated, Wi-Fi, Split AC

Discover Wailea Ekahi 39E - Breathtaking Ocean Views, Renovated, Wi-Fi, Split AC
Kihei
Image gallery for Extra spacious, private, 1BR/2BA, front row, ocean view at Maui Kamaole (A101)

Extra spacious, private, 1BR/2BA, front row, ocean view at Maui Kamaole (A101)
Kihei
Image gallery for Mana Kai 314 - Experience Stunning Coastal Views on Keawakapu Beach, Split AC

Mana Kai 314 - Experience Stunning Coastal Views on Keawakapu Beach, Split AC
Kihei
Image gallery for Amazing Ocean View Condo Walk to The Beach

Amazing Ocean View Condo Walk to The Beach
Kihei
Image gallery for Ekahi 8F, Oceanview Studio, extremely close to Beach and Main Pool! 2nd Floor

Ekahi 8F, Oceanview Studio, extremely close to Beach and Main Pool! 2nd Floor
Kihei
Image gallery for The Best of 'The Palms' - Panoramic Views, Private End Unit #1102

The Best of 'The Palms' - Panoramic Views, Private End Unit #1102
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
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 Makena Surf G-201 - Corner Unit with Amazing Views, Pools, Pickleball & Peloton

Makena Surf G-201 - Corner Unit with Amazing Views, Pools, Pickleball & Peloton
Kihei
Image gallery for Wailea Ekolu 1514 - Ocean Views, Private Lanais, Spacious 2-Story in Beautiful Wailea

Wailea Ekolu 1514 - Ocean Views, Private Lanais, Spacious 2-Story in Beautiful Wailea
Kihei
Image gallery for Paradise in Maui - the Maui Kamaole Resort!

Paradise in Maui - the Maui Kamaole Resort!
Kihei
Image gallery for Ekahi 29C, Ocean View, Steps away from the pool

Ekahi 29C, Ocean View, Steps away from the pool
Kihei
Image gallery for Kihei Getaway in Paradise

Kihei Getaway in Paradise
Kihei
Image gallery for 1BR/2BA Maui Kamaole/Wailea Border. K Cluster @ Tropical Pool!

1BR/2BA Maui Kamaole/Wailea Border. K Cluster @ Tropical Pool!
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
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 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 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
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 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
Plans change. We get that. With Bookabach, you can search, select 'free cancellation,' and see all rentals in Wailea with flexible cancellation policies.