Holiday rentals near Shops at Wailea
We found 4,737 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals close to Shops at Wailea that can be your home away from home. Whether you're travelling with your children or with friends, holiday rentals have the amenities that you need and want for your stay, which might include parking and a washer and dryer. You're sure to find a property to rent that has what everyone needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Shops at Wailea
Showing deals for:21 Nov - 28 Nov
Image gallery for Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets
1010 out of 10 rating
Exceptional
(181 reviews)
Oceanfront, Exceptionally Remodeled, Split A/C, King bed, OH the sunsets
Kihei, HI
7% off
Price is NZ$6,485
NZ$6,485
NZ$926 per night
includes taxes & fees
Image gallery for Makena Surf B202 - Beachfront Platinum Condo; Gorgeous Ocean & Crater Views.
1010 out of 10 rating
Exceptional
(50 reviews)
Makena Surf B202 - Beachfront Platinum Condo; Gorgeous Ocean & Crater Views.
Kihei, HI
8% off
Price is NZ$16,383
NZ$16,383
NZ$2,340 per night
includes taxes & fees
Image gallery for Best view in Maui. Condo fully remodeled. August special 10% weekly discount.
9.89.8 out of 10 rating
Exceptional
(49 reviews)
Best view in Maui. Condo fully remodeled. August special 10% weekly discount.
Maalaea, HI
7% off
Price is NZ$8,008
NZ$8,008
NZ$1,144 per night
includes taxes & fees
Image gallery for Newly Renovated Kihei Condo with Sunset Views – Steps From a Beautiful Beach!
9.89.8 out of 10 rating
Exceptional
(130 reviews)
Newly Renovated Kihei Condo with Sunset Views – Steps From a Beautiful Beach!
Kihei, HI
7% off
Price is NZ$4,490
NZ$4,490
NZ$641 per night
includes taxes & fees
Image gallery for Maui Banyan #G-309 Ocean View 2-bedroom condo in fabulous Kihei
1010 out of 10 rating
Exceptional
(5 reviews)
Maui Banyan #G-309 Ocean View 2-bedroom condo in fabulous Kihei
Kihei, HI
7% off
Price is NZ$7,061
NZ$7,061
NZ$1,009 per night
includes taxes & fees
Image gallery for Ocean Front with Spectacular View
9.49.4 out of 10 rating
Exceptional
(63 reviews)
Ocean Front with Spectacular View
Maalaea, HI
8% off
Price is NZ$3,230
NZ$3,230
NZ$461 per night
includes taxes & fees
Image gallery for Endless Waves, Incredible Direct Oceanfront Views!
9.89.8 out of 10 rating
Exceptional
(73 reviews)
Endless Waves, Incredible Direct Oceanfront Views!
Maalaea, HI
7% off
Price is NZ$4,009
NZ$4,009
NZ$573 per night
includes taxes & fees
Image gallery for 50 steps to the Ocean! Newly remodeled!
9.29.2 out of 10 rating
Wonderful
(33 reviews)
50 steps to the Ocean! Newly remodeled!
Maalaea, HI
7% off
Price is NZ$3,002
NZ$3,002
NZ$429 per night
includes taxes & fees
Image gallery for Breath taking ocean and volcano views! Pool,Close to beaches and everything else
9.89.8 out of 10 rating
Exceptional
(157 reviews)
Breath taking ocean and volcano views! Pool,Close to beaches and everything else
Kihei, HI
8% off
Price is NZ$22,611
NZ$22,611
NZ$3,230 per night
includes taxes & fees
Image gallery for Wailea 1 BR Condo, amazing lanai, close to everything, good pricing
9.89.8 out of 10 rating
Exceptional
(155 reviews)
Wailea 1 BR Condo, amazing lanai, close to everything, good pricing
Kihei, HI
7% off
Price is NZ$3,439
NZ$3,439
NZ$491 per night
includes taxes & fees
Image gallery for Completely remodeled 2 bedroom King bed AC Kauhale Makai on the top floor
1010 out of 10 rating
Exceptional
(82 reviews)
Completely remodeled 2 bedroom King bed AC Kauhale Makai on the top floor
Kihei, HI
7% off
Price is NZ$9,718
NZ$9,718
NZ$1,388 per night
includes taxes & fees
Image gallery for Kanai A Nalu-Spectacular Whale Watching, Beachfront, Wifi & Split Air thru out
9.69.6 out of 10 rating
Exceptional
(94 reviews)
Kanai A Nalu-Spectacular Whale Watching, Beachfront, Wifi & Split Air thru out
Maalaea, HI
7% off
Price is NZ$4,236
NZ$4,236
NZ$605 per night
includes taxes & fees
Image gallery for Updated Kauhale Makai unit 610 1 bedroom top floor, king bed, AC
1010 out of 10 rating
Exceptional
(63 reviews)
Updated Kauhale Makai unit 610 1 bedroom top floor, king bed, AC
Kihei, HI
8% off
Price is NZ$7,115
NZ$7,115
NZ$1,016 per night
includes taxes & fees
Image gallery for Huge Ocean Views! Direct Ocean Front Condo Sugar Beach Resort #527
9.69.6 out of 10 rating
Exceptional
(133 reviews)
Huge Ocean Views! Direct Ocean Front Condo Sugar Beach Resort #527
Kihei, HI
7% off
Price is NZ$5,284
NZ$5,284
NZ$755 per night
includes taxes & fees
Image gallery for Lovely Palms at Wailea #406, spacious, large lanai, Full A/C, close to beach!
1010 out of 10 rating
Exceptional
(5 reviews)
Lovely Palms at Wailea #406, spacious, large lanai, Full A/C, close to beach!
Kihei, HI
7% off
Price is NZ$4,864
NZ$4,864
NZ$695 per night
includes taxes & fees
Image gallery for Sleeps 4, Full kitchen & AC. Pool, hot tub, tennis court, bbq grills! And Beach!
9.89.8 out of 10 rating
Exceptional
(72 reviews)
Sleeps 4, Full kitchen & AC. Pool, hot tub, tennis court, bbq grills! And Beach!
Kihei, HI
7% off
Price is NZ$3,193
NZ$3,193
NZ$456 per night
includes taxes & fees
Image gallery for Summer specials of 20-30% off for stays of a week or more!
9.69.6 out of 10 rating
Exceptional
(124 reviews)
Summer specials of 20-30% off for stays of a week or more!
Kihei, HI
11% off
Price is NZ$3,395
NZ$3,395
NZ$485 per night
includes taxes & fees
Image gallery for Studio apt. with A/C, Fridge, Semi-Private pool in the Center of kihei
9.49.4 out of 10 rating
Exceptional
(72 reviews)
Studio apt. with A/C, Fridge, Semi-Private pool in the Center of kihei
Kihei, HI
8% off
Price is NZ$2,075
NZ$2,075
NZ$296 per night
includes taxes & fees
Image gallery for Oceanfront, Million-Dollar-View, Newly renovated! B421
1010 out of 10 rating
Exceptional
(183 reviews)
Oceanfront, Million-Dollar-View, Newly renovated! B421
Kihei, HI
7% off
Price is NZ$9,693
NZ$9,693
NZ$1,385 per night
includes taxes & fees
Image gallery for Relaxing Wailea Ekahi Garden Hideaway.
9.89.8 out of 10 rating
Exceptional
(54 reviews)
Relaxing Wailea Ekahi Garden Hideaway.
Kihei, HI
7% off
Price is NZ$5,891
NZ$5,891
NZ$842 per night
includes taxes & fees
Image gallery for Can't get any closer to the Ocean#2
9.89.8 out of 10 rating
Exceptional
(66 reviews)
Can't get any closer to the Ocean#2
Kihei, HI
8% off
Price is NZ$5,850
NZ$5,850
NZ$836 per night
includes taxes & fees
Image gallery for Sugar Beach Oceanfront Condo with Spectacular Views and Steps to the Beach
9.89.8 out of 10 rating
Exceptional
(51 reviews)
Sugar Beach Oceanfront Condo with Spectacular Views and Steps to the Beach
Kihei, HI
7% off
Price is NZ$3,890
NZ$3,890
NZ$556 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 rating
Exceptional
(54 reviews)
Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!
Maalaea, HI
7% off
Price is NZ$4,166
NZ$4,166
NZ$595 per night
includes taxes & fees
Image gallery for Best unit on property! Modern, Ocean Views! Beach, Pool, Whales! Video Tour!
1010 out of 10 rating
Exceptional
(8 reviews)
Best unit on property! Modern, Ocean Views! Beach, Pool, Whales! Video Tour!
Kihei, HI
7% off
Price is NZ$4,457
NZ$4,457
NZ$637 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Shops at Wailea
Spacious End Unit
Sleeps 2 · 1 bedroom · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
81 reviews(81 reviews)
Coursefront Condo with Shared Pool & Hot Tub, Private W/D, WiFi, and Ocean View
Sleeps 4 · 1 bedroom · 2 bathrooms
1010 out of 10
Exceptionalexceptional
26 reviews(26 reviews)
Aston Maui Hill
Sleeps 6 · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
815 reviews(815 reviews)
Wailea Ekolu #405 SUPREME OCEAN VIEW on Wailea Golf Course w/ FULL A/C
Sleeps 4 · 2 bedrooms · 2 bathrooms
Stunning Golf Course & Garden Views - WAILEA GRAND CHAMPION #142
Sleeps 4 · 1 bedroom · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
Grand Champions 12, Great Wailea Location!
Sleeps 6 · 2 bedrooms · 2 bathrooms
7.67.6 out of 10
Goodgood
10 reviews(10 reviews)
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