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Wailea-Makena long stay rentals
Stay a week, a month or longer in a comfortable place all your own
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:26 Jan - 23 Feb
Image gallery for Wailea Luxury Retreat | Walk to Beach & Shops
9.29.2 out of 10, Wonderful, (7 reviews)
Wonderful
(7 reviews)
Wailea Luxury Retreat | Walk to Beach & Shops
Kihei, HI
17% off
Price is NZ$20,576
NZ$20,576
for 28 nights, 1 apartment
NZ$735 per night
includes taxes & fees
Image gallery for Shores of Maui - Ocean View with pool
1010 out of 10, Exceptional, (119 reviews)
Exceptional
(119 reviews)
Shores of Maui - Ocean View with pool
Kihei, HI
8% off
Price is NZ$18,385
NZ$18,385
for 28 nights, 1 apartment
NZ$657 per night
includes taxes & fees
Image gallery for Great for families and couples. Next to a tropical pool in Hawaiian landscape.
9.69.6 out of 10, Exceptional, (202 reviews)
Exceptional
(202 reviews)
Great for families and couples. Next to a tropical pool in Hawaiian landscape.
Kihei, HI
8% off
Price is NZ$26,307
NZ$26,307
for 28 nights, 1 apartment
NZ$940 per night
includes taxes & fees
Image gallery for Palms At Wailea 1801, 2Bd 2Bath, FULL AC, Sleep 6, New Owner, Renovated,
9.89.8 out of 10, Exceptional, (22 reviews)
Exceptional
(22 reviews)
Palms At Wailea 1801, 2Bd 2Bath, FULL AC, Sleep 6, New Owner, Renovated,
Kihei, HI
8% off
Price is NZ$33,588
NZ$33,588
for 28 nights, 1 apartment
NZ$1,200 per night
includes taxes & fees
Image gallery for ~Amazing Ocean View on 3rd flr~ MAUI AWAITS YOU!!
8.88.8 out of 10, Excellent, (39 reviews)
Excellent
(39 reviews)
~Amazing Ocean View on 3rd flr~ MAUI AWAITS YOU!!
Kihei, HI
8% off
Price is NZ$13,887
NZ$13,887
for 28 nights, 1 apartment
NZ$496 per night
includes taxes & fees
Image gallery for Kalama Terrace P-307 - 3rd-floor walkup, 7 min walk to Charley Young Beach, AC!
9.69.6 out of 10, Exceptional, (179 reviews)
Exceptional
(179 reviews)
Kalama Terrace P-307 - 3rd-floor walkup, 7 min walk to Charley Young Beach, AC!
Kihei, HI
16% off
Price is NZ$12,386
NZ$12,386
for 28 nights, 1 apartment
NZ$442 per night
includes taxes & fees
Image gallery for Maui Kamaole, 2 lanais, queen sofa beds, quiet, eco friendly, south Kihei condo
1010 out of 10, Exceptional, (47 reviews)
Exceptional
(47 reviews)
Maui Kamaole, 2 lanais, queen sofa beds, quiet, eco friendly, south Kihei condo
Kihei, HI
16% off
Price is NZ$22,877
NZ$22,877
for 28 nights, 1 apartment
NZ$817 per night
includes taxes & fees
Image gallery for PARADISE RV .You won't forget your time in this romantic, memorable place.
1010 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)
PARADISE RV .You won't forget your time in this romantic, memorable place.
Kihei, HI
8% off
Price is NZ$8,569
NZ$8,569
for 28 nights, 1 home
NZ$306 per night
includes taxes & fees
Image gallery for Kihei Paradise! 1bed/2baths, 5 mins to beach
1010 out of 10, Exceptional, (2 reviews)
Exceptional
(2 reviews)
Kihei Paradise! 1bed/2baths, 5 mins to beach
Kihei, HI
8% off
Price is NZ$14,785
NZ$14,785
for 28 nights, 1 apartment
NZ$528 per night
includes taxes & fees
Image gallery for Serene Maui Retreat | Walk to Beach & Shops
8.08.0 out of 10, Very good, (2 reviews)
Very good
(2 reviews)
Serene Maui Retreat | Walk to Beach & Shops
Kihei, HI
17% off
Price is NZ$20,524
NZ$20,524
for 28 nights, 1 apartment
NZ$733 per night
includes taxes & fees
Image gallery for Experience Maui in Comfort!! ~Fully Furnished 1b/2b Recently Updated Condo
9.89.8 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
Experience Maui in Comfort!! ~Fully Furnished 1b/2b Recently Updated Condo
Kihei, HI
8% off
Price is NZ$17,290
NZ$17,290
for 28 nights, 1 apartment
NZ$618 per night
includes taxes & fees
Image gallery for Kanai A Nalu - Top floor Oceanfront condo w Pool
1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Kanai A Nalu - Top floor Oceanfront condo w Pool
Maalaea, HI
16% off
Price is NZ$42,659
NZ$42,659
for 28 nights, 1 apartment
NZ$1,524 per night
includes taxes & fees
Image gallery for Steps to Beach | Hot Tub | Luxe Maui Retreat
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
Steps to Beach | Hot Tub | Luxe Maui Retreat
Kihei, HI
17% off
Price is NZ$18,353
NZ$18,353
for 28 nights, 1 apartment
NZ$655 per night
includes taxes & fees
Image gallery for Kamaole Beach 1BR/Ocean View & AC/2 Pools & Tennis, Full Kitchen, Walk to Dining
9.09.0 out of 10, Wonderful, (18 reviews)
Wonderful
(18 reviews)
Kamaole Beach 1BR/Ocean View & AC/2 Pools & Tennis, Full Kitchen, Walk to Dining
Kihei, HI
8% off
Price is NZ$16,318
NZ$16,318
for 28 nights, 1 apartment
NZ$583 per night
includes taxes & fees
Image gallery for Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!
9.49.4 out of 10, Exceptional, (56 reviews)
Exceptional
(56 reviews)
Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!
Maalaea, HI
8% off
Price is NZ$32,259
NZ$32,259
for 28 nights, 1 apartment
NZ$1,152 per night
includes taxes & fees
Image gallery for W/M DISCOUNTS + FULL KITCHEN + COMFY KING + GREEN VIEW + RESERVED PARKING SPOT
9.89.8 out of 10, Exceptional, (171 reviews)
Exceptional
(171 reviews)
W/M DISCOUNTS + FULL KITCHEN + COMFY KING + GREEN VIEW + RESERVED PARKING SPOT
Kihei, HI
21% off
Price is NZ$16,349
NZ$16,349
for 28 nights, 1 apartment
NZ$584 per night
includes taxes & fees
Image gallery for Experience Kamaole Sands 4-409 - Ocean Views, Spacious, Renovated, Wi-Fi, AC!
9.89.8 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Experience Kamaole Sands 4-409 - Ocean Views, Spacious, Renovated, Wi-Fi, AC!
Kihei, HI
16% off
Price is NZ$19,985
NZ$19,985
for 28 nights, 1 apartment
NZ$714 per night
includes taxes & fees
Image gallery for South Kihei Condo; Steps to Beach!!
1010 out of 10, Exceptional, (1 review)
Exceptional
(1 review)
South Kihei Condo; Steps to Beach!!
Kihei, HI
8% off
Price is NZ$22,596
NZ$22,596
for 28 nights, 1 apartment
NZ$807 per night
includes taxes & fees
Image gallery for Great Ocean View, Privacy-a Sweet Spot Near the Office, Pool, BBQ, Park, Beach!
9.09.0 out of 10, Wonderful, (18 reviews)
Wonderful
(18 reviews)
Great Ocean View, Privacy-a Sweet Spot Near the Office, Pool, BBQ, Park, Beach!
Kihei, HI
8% off
Price is NZ$16,520
NZ$16,520
for 28 nights, 1 apartment
NZ$590 per night
includes taxes & fees
Image gallery for MKO E202 Remodeled 2BD Retreat wAC Pool Near Beach
8.88.8 out of 10, Excellent, (12 reviews)
Excellent
(12 reviews)
MKO E202 Remodeled 2BD Retreat wAC Pool Near Beach
Kihei, HI
11% off
Price is NZ$21,710
NZ$21,710
for 28 nights, 1 apartment
NZ$775 per night
includes taxes & fees
Image gallery for Summer Sale! - Ocean View, King Beds, Split-AC - Kamaole Sands 4-407 - Book Now!
9.09.0 out of 10, Wonderful, (11 reviews)
Wonderful
(11 reviews)
Summer Sale! - Ocean View, King Beds, Split-AC - Kamaole Sands 4-407 - Book Now!
Kihei, HI
16% off
Price is NZ$19,985
NZ$19,985
for 28 nights, 1 apartment
NZ$714 per night
includes taxes & fees
Image gallery for Updated 1BD/1BA in the best South Kihei location! (quiet split A/C + great WiFi)
1010 out of 10, Exceptional, (8 reviews)
Exceptional
(8 reviews)
Updated 1BD/1BA in the best South Kihei location! (quiet split A/C + great WiFi)
Kihei, HI
12% off
Price is NZ$20,736
NZ$20,736
for 28 nights, 1 apartment
NZ$741 per night
includes taxes & fees
Image gallery for Beach Retreat | Walk to Maui’s Best Shores
8.88.8 out of 10, Excellent, (8 reviews)
Excellent
(8 reviews)
Beach Retreat | Walk to Maui’s Best Shores
Kihei, HI
17% off
Price is NZ$19,316
NZ$19,316
for 28 nights, 1 apartment
NZ$690 per night
includes taxes & fees
Image gallery for MAUI'S BEST VALUE Upgraded Luxury Condo Amazing Views Steps to A+ Kamaole Beach
1010 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)
MAUI'S BEST VALUE Upgraded Luxury Condo Amazing Views Steps to A+ Kamaole Beach
Kihei, HI
8% off
Price is NZ$17,018
NZ$17,018
for 28 nights, 1 apartment
NZ$608 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