Wailea-Makena long stay rentals
Stay a week, a month or longer in a comfortable place all your own
Relax—Stayz 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 Stayz. 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
Properties highly-rated for stays of 28 nights or longer, with space to feel right at home
Showing deals for:22 June - 20 July
Image gallery for Maui Banyan king, 2 bath,steps to Kamaole beach,great walking spot, free parking
1010 out of 10, Exceptional, (84 reviews)
Exceptional
(84 reviews)
Maui Banyan king, 2 bath,steps to Kamaole beach,great walking spot, free parking
Kihei
8% off
Price is AU$9,206
AU$9,206
for 28 nights, 1 apartment
AU$329 per night
includes taxes & fees
Image gallery for Kihei Kai Nani 238 - Garden View 1 Bedroom, Split AC, Steps to Kamaole II Beach!
9.69.6 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)
Kihei Kai Nani 238 - Garden View 1 Bedroom, Split AC, Steps to Kamaole II Beach!
Kihei
15% off
Price is AU$8,661
AU$8,661
for 28 nights, 1 apartment
AU$309 per night
includes taxes & fees
Image gallery for The Blue Tide House: Steps to Maui beaches + nearby eats
1010 out of 10, Exceptional, (5 reviews)
Exceptional
(5 reviews)
The Blue Tide House: Steps to Maui beaches + nearby eats
Kihei
8% off
Price is AU$10,386
AU$10,386
for 28 nights, 1 apartment
AU$371 per night
includes taxes & fees
Image gallery for Charming Studio at Maui Banyan Resort - Walk to Beach, Pools, AC, Beach Gear
9.09.0 out of 10, Wonderful, (12 reviews)
Wonderful
(12 reviews)
Charming Studio at Maui Banyan Resort - Walk to Beach, Pools, AC, Beach Gear
Kihei
8% off
Price is AU$6,848
AU$6,848
for 28 nights, 1 room
AU$245 per night
includes taxes & fees
Image gallery for Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!
1010 out of 10, Exceptional, (71 reviews)
Exceptional
(71 reviews)
Panoramic Ocean Views! Amazing Interior! Spectacular Wailea Listing!
Kihei
12% off
Price is AU$10,947
AU$10,947
for 28 nights, 1 apartment
AU$391 per night
includes taxes & fees
Image gallery for Incredible Top Floor Amazing Ocean Views and your own Assigned Parking space.
9.89.8 out of 10, Exceptional, (318 reviews)
Exceptional
(318 reviews)
Incredible Top Floor Amazing Ocean Views and your own Assigned Parking space.
Kihei
8% off
Price is AU$8,630
AU$8,630
for 28 nights, 1 apartment
AU$308 per night
includes taxes & fees
Image gallery for Great Wailea studio Condo
9.49.4 out of 10, Exceptional, (156 reviews)
Exceptional
(156 reviews)
Great Wailea studio Condo
Kihei
12% off
Price is AU$9,777
AU$9,777
for 28 nights, 1 apartment
AU$349 per night
includes taxes & fees
Image gallery for Ekahi 27A: Priceless Ocean View from a Private Lanai
1010 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)
Ekahi 27A: Priceless Ocean View from a Private Lanai
Kihei
24% off
Price is AU$14,775
AU$14,775
for 28 nights, 1 apartment
AU$528 per night
includes taxes & fees
Image gallery for Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!
9.29.2 out of 10, Wonderful, (19 reviews)
Wonderful
(19 reviews)
Oceanside Cozy, Clean, Casual Suite - steps to beach and amenities!
Kihei
8% off
Price is AU$13,950
AU$13,950
for 28 nights, 1 apartment
AU$498 per night
includes taxes & fees
Image gallery for Wailea Ekolu 304 - Luxurious Front-Row Unit with Amazing Ocean & Golf Views
9.69.6 out of 10, Exceptional, (94 reviews)
Exceptional
(94 reviews)
Wailea Ekolu 304 - Luxurious Front-Row Unit with Amazing Ocean & Golf Views
Kihei
8% off
Price is AU$11,960
AU$11,960
for 28 nights, 1 apartment
AU$427 per night
includes taxes & fees
Image gallery for Kamaole Sands 4-306 - Steps to Kamaole III Beach - Split AC + Pool + King Bed
9.69.6 out of 10, Exceptional, (57 reviews)
Exceptional
(57 reviews)
Kamaole Sands 4-306 - Steps to Kamaole III Beach - Split AC + Pool + King Bed
Kihei
15% off
Price is AU$9,237
AU$9,237
for 28 nights, 1 apartment
AU$330 per night
includes taxes & fees
Image gallery for Kamaole Sands 4-213 - Beautiful Modern Renovation - Bright & Open - Split AC
1010 out of 10, Exceptional, (47 reviews)
Exceptional
(47 reviews)
Kamaole Sands 4-213 - Beautiful Modern Renovation - Bright & Open - Split AC
Kihei
15% off
Price is AU$11,031
AU$11,031
for 28 nights, 1 apartment
AU$394 per night
includes taxes & fees
Image gallery for Fabulous Ocean Views from Front Row Condo!
9.89.8 out of 10, Exceptional, (133 reviews)
Exceptional
(133 reviews)
Fabulous Ocean Views from Front Row Condo!
Kihei
20% off
Price is AU$12,903
AU$12,903
for 28 nights, 1 apartment
AU$461 per night
includes taxes & fees
Image gallery for Get an early start on summer with Aloha Savings!
9.69.6 out of 10, Exceptional, (117 reviews)
Exceptional
(117 reviews)
Get an early start on summer with Aloha Savings!
Kihei
8% off
Price is AU$9,699
AU$9,699
for 28 nights, 1 apartment
AU$346 per night
includes taxes & fees
Image gallery for Superior 1 Bed Bright decor Part ocean view King Bed No risk of zoning change
1010 out of 10, Exceptional, (168 reviews)
Exceptional
(168 reviews)
Superior 1 Bed Bright decor Part ocean view King Bed No risk of zoning change
Kihei
8% off
Price is AU$7,720
AU$7,720
for 28 nights, 1 apartment
AU$276 per night
includes taxes & fees
Image gallery for Great location! Only 200 steps to KAM II beach, great for families!
9.49.4 out of 10, Exceptional, (61 reviews)
Exceptional
(61 reviews)
Great location! Only 200 steps to KAM II beach, great for families!
Kihei
8% off
Price is AU$11,812
AU$11,812
for 28 nights, 1 apartment
AU$422 per night
includes taxes & fees
Image gallery for Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
1010 out of 10, Exceptional, (156 reviews)
Exceptional
(156 reviews)
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
Kihei
8% off
Price is AU$15,763
AU$15,763
for 28 nights, 1 apartment
AU$563 per night
includes taxes & fees
Image gallery for 2 bdrm 2 Bath Condo with Partial Ocean Views, Steps away from Kamaole III Beach
9.49.4 out of 10, Exceptional, (36 reviews)
Exceptional
(36 reviews)
2 bdrm 2 Bath Condo with Partial Ocean Views, Steps away from Kamaole III Beach
Kihei
8% off
Price is AU$12,723
AU$12,723
for 28 nights, 1 apartment
AU$454 per night
includes taxes & fees
Image gallery for Haleakala Shores A-302 - Stunning Ocean Views, Beautiful Renovation, Wi-Fi, & AC
9.89.8 out of 10, Exceptional, (51 reviews)
Exceptional
(51 reviews)
Haleakala Shores A-302 - Stunning Ocean Views, Beautiful Renovation, Wi-Fi, & AC
Kihei
16% off
Price is AU$14,598
AU$14,598
for 28 nights, 1 apartment
AU$521 per night
includes taxes & fees
Image gallery for Kamaole Sands 6-303 - Courtyard and Ocean Views from Renovated 3rd Floor Condo
9.69.6 out of 10, Exceptional, (48 reviews)
Exceptional
(48 reviews)
Kamaole Sands 6-303 - Courtyard and Ocean Views from Renovated 3rd Floor Condo
Kihei
15% off
Price is AU$12,592
AU$12,592
for 28 nights, 1 apartment
AU$450 per night
includes taxes & fees
Image gallery for LUXURIOUS Wailea BEACH Direct Ocean Front Property Wailea Ekahi 42A 1 Bed/2B
9.89.8 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
LUXURIOUS Wailea BEACH Direct Ocean Front Property Wailea Ekahi 42A 1 Bed/2B
Kihei
8% off
Price is AU$21,323
AU$21,323
for 28 nights, 1 apartment
AU$762 per night
includes taxes & fees
Image gallery for Private Ocean View Cottage Overlooking Wailea
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
Private Ocean View Cottage Overlooking Wailea
Kihei
8% off
Price is AU$12,792
AU$12,792
for 28 nights, 1 cottage
AU$457 per night
includes taxes & fees
Image gallery for Beautifully renovated luxury condo steps from the sand on premier Kihei beach!
9.89.8 out of 10, Exceptional, (89 reviews)
Exceptional
(89 reviews)
Beautifully renovated luxury condo steps from the sand on premier Kihei beach!
Kihei
16% off
Price is AU$10,693
AU$10,693
for 28 nights, 1 apartment
AU$382 per night
includes taxes & fees
Image gallery for 3 minute walk to the beach!! Newly renovated 1 bedroom 2 bath condo
9.09.0 out of 10, Wonderful, (4 reviews)
Wonderful
(4 reviews)
3 minute walk to the beach!! Newly renovated 1 bedroom 2 bath condo
Kihei
8% off
Price is AU$10,348
AU$10,348
for 28 nights, 1 apartment
AU$370 per night
includes taxes & fees
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 Stayz, making stays of a month or more excellent value.
Entire homes, maximum privacy
Looking for your own place to retreat to? On Stayz, 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 Stayz 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
Stayz 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
Stayz'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 Stayz, you can search, select 'free cancellation,' and see all rentals in Wailea-Makena with flexible cancellation policies.