Holiday rentals near Shops at Wailea
We found 4,616 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:1 Aug - 8 Aug
Image gallery for Kula Luxury Retreat With Stunning Ocean & Mountain Views!
1010 out of 10 rating
Exceptional
(72 reviews)
Kula Luxury Retreat With Stunning Ocean & Mountain Views!
Kihei, HI
8% off
Price is NZ$18,907
NZ$18,907
NZ$2,701 per night
includes taxes & fees
Image gallery for Just another day in Paradise!
9.89.8 out of 10 rating
Exceptional
(111 reviews)
Just another day in Paradise!
Kihei, HI
7% off
Price is NZ$6,677
NZ$6,677
NZ$954 per night
includes taxes & fees
Image gallery for Maui Paradise: Steps to Sand & Sun. Blg#1-Ocean View, AC's, Fast Wifi, 1st Floor
1010 out of 10 rating
Exceptional
(31 reviews)
Maui Paradise: Steps to Sand & Sun. Blg#1-Ocean View, AC's, Fast Wifi, 1st Floor
Kihei, HI
7% off
Price is NZ$3,753
NZ$3,753
NZ$536 per night
includes taxes & fees
Image gallery for Nice Large Floor Plan / Pool View Unit B-201
1010 out of 10 rating
Exceptional
(153 reviews)
Nice Large Floor Plan / Pool View Unit B-201
Kihei, HI
7% off
Price is NZ$4,240
NZ$4,240
NZ$606 per night
includes taxes & fees
Image gallery for Oceanside -Walk to Beach- Modern & Serene- 2BD, 2BA- Kihei Alii Kai-Full Remodel
1010 out of 10 rating
Exceptional
(23 reviews)
Oceanside -Walk to Beach- Modern & Serene- 2BD, 2BA- Kihei Alii Kai-Full Remodel
Kihei, HI
7% off
Price is NZ$6,216
NZ$6,216
NZ$888 per night
includes taxes & fees
Image gallery for Fully remodeled & equipped condo, steps to amazing beaches!
9.49.4 out of 10 rating
Exceptional
(158 reviews)
Fully remodeled & equipped condo, steps to amazing beaches!
Kihei, HI
7% off
Price is NZ$5,180
NZ$5,180
NZ$740 per night
includes taxes & fees
Image gallery for Beautiful 2 Bedroom Oceanview Condo at Maui Kamaole Perfect Maui Escape! 5 Star!
9.89.8 out of 10 rating
Exceptional
(61 reviews)
Beautiful 2 Bedroom Oceanview Condo at Maui Kamaole Perfect Maui Escape! 5 Star!
Kihei, HI
14% off
Price is NZ$4,839
NZ$4,839
NZ$691 per night
includes taxes & fees
Image gallery for Beautiful OCEAN View! Across from the BEACH! From 140 a night!
9.09.0 out of 10 rating
Wonderful
(136 reviews)
Beautiful OCEAN View! Across from the BEACH! From 140 a night!
Kihei, HI
7% off
Price is NZ$2,437
NZ$2,437
NZ$348 per night
includes taxes & fees
Image gallery for Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
1010 out of 10 rating
Exceptional
(86 reviews)
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Kihei, HI
7% off
Price is NZ$9,673
NZ$9,673
NZ$1,382 per night
includes taxes & fees
Image gallery for Wailea Ekahi 51F Oceanview - Walk to Beach
9.89.8 out of 10 rating
Exceptional
(95 reviews)
Wailea Ekahi 51F Oceanview - Walk to Beach
Kihei, HI
8% off
Price is NZ$4,385
NZ$4,385
NZ$626 per night
includes taxes & fees
Image gallery for Relaxing Wailea Ekahi Garden Hideaway.
9.89.8 out of 10 rating
Exceptional
(53 reviews)
Relaxing Wailea Ekahi Garden Hideaway.
Kihei, HI
7% off
Price is NZ$4,196
NZ$4,196
NZ$599 per night
includes taxes & fees
Image gallery for Watch the whales from your own personal lanai!!!!
9.89.8 out of 10 rating
Exceptional
(85 reviews)
Watch the whales from your own personal lanai!!!!
Kihei, HI
7% off
Price is NZ$5,966
NZ$5,966
NZ$852 per night
includes taxes & fees
Image gallery for NEWLY REMODELED! Beautiful & Spacious- Two Story Wailea Ocean View 2BR/2.5BA
1010 out of 10 rating
Exceptional
(102 reviews)
NEWLY REMODELED! Beautiful & Spacious- Two Story Wailea Ocean View 2BR/2.5BA
Kihei, HI
7% off
Price is NZ$7,970
NZ$7,970
NZ$1,139 per night
includes taxes & fees
Image gallery for 3 minute walk to beach in South Maui!
9.89.8 out of 10 rating
Exceptional
(113 reviews)
3 minute walk to beach in South Maui!
Kihei, HI
7% off
Price is NZ$5,104
NZ$5,104
NZ$729 per night
includes taxes & fees
Image gallery for Resort condo situated in spectacular oceanfront grounds with pools.
1010 out of 10 rating
Exceptional
(32 reviews)
Resort condo situated in spectacular oceanfront grounds with pools.
Kihei, HI
8% off
Price is NZ$5,089
NZ$5,089
NZ$727 per night
includes taxes & fees
Image gallery for Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
9.69.6 out of 10 rating
Exceptional
(106 reviews)
Tropical Garden Family Home - Sleeps 6 - Walk to Beach, BBQ, Hot Tub
Kihei, HI
7% off
Price is NZ$9,175
NZ$9,175
NZ$1,311 per night
includes taxes & fees
Image gallery for Beautiful Maui Home Away from Home
9.89.8 out of 10 rating
Exceptional
(129 reviews)
Beautiful Maui Home Away from Home
Kihei, HI
7% off
Price is NZ$2,712
NZ$2,712
NZ$387 per night
includes taxes & fees
Image gallery for Modern Luxury 2nd-Floor 2Bd/2Ba Retreat with Ultra-Quiet A/C, & 6'x5' Shower
9.89.8 out of 10 rating
Exceptional
(59 reviews)
Modern Luxury 2nd-Floor 2Bd/2Ba Retreat with Ultra-Quiet A/C, & 6'x5' Shower
Kihei, HI
7% off
Price is NZ$6,013
NZ$6,013
NZ$859 per night
includes taxes & fees
Image gallery for Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
1010 out of 10 rating
Exceptional
(182 reviews)
Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004
Kihei, HI
8% off
Price is NZ$6,998
NZ$6,998
NZ$1,000 per night
includes taxes & fees
Image gallery for Maalaea Maui Oceanfront Condo -Mountain Views & Whale Watching
9.49.4 out of 10 rating
Exceptional
(97 reviews)
Maalaea Maui Oceanfront Condo -Mountain Views & Whale Watching
Maalaea, HI
5% off
Price is NZ$3,771
NZ$3,771
NZ$539 per night
includes taxes & fees
Image gallery for Spacious 3 BR, Walk to Best Beaches & Shops in South Kihei! Sleeps 8
9.89.8 out of 10 rating
Exceptional
(155 reviews)
Spacious 3 BR, Walk to Best Beaches & Shops in South Kihei! Sleeps 8
Kihei, HI
7% off
Price is NZ$8,848
NZ$8,848
NZ$1,264 per night
includes taxes & fees
Image gallery for Oceanfront Condo - Steps to the beach, amazing views, perfect for whale watching
9.89.8 out of 10 rating
Exceptional
(129 reviews)
Oceanfront Condo - Steps to the beach, amazing views, perfect for whale watching
Maalaea, HI
7% off
Price is NZ$4,142
NZ$4,142
NZ$592 per night
includes taxes & fees
Image gallery for LUXURY PENTHOUSE 2 BDRM OCEANFRONT BUILDING: Just steps from the beach!
1010 out of 10 rating
Exceptional
(129 reviews)
LUXURY PENTHOUSE 2 BDRM OCEANFRONT BUILDING: Just steps from the beach!
Kihei, HI
6% off
Price is NZ$8,253
NZ$8,253
NZ$1,179 per night
includes taxes & fees
Image gallery for Luxury Meets Affordability! Permit Number: BBKM20150003
9.49.4 out of 10 rating
Exceptional
(114 reviews)
Luxury Meets Affordability! Permit Number: BBKM20150003
Kihei, HI
7% off
Price is NZ$2,527
NZ$2,527
NZ$361 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Shops at Wailea
Wailea Serenity | 2 Bed, 2 Bath
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
32 reviews(32 reviews)
Wailea Grand Champions - CoralTree Residence Collection
Sleeps 4 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
706 reviews(706 reviews)
Grand Champions #147 Golf Course Views Full Kitchen AC Throughout
Sleeps 4 · 2 bedrooms · 2 bathrooms
Spacious, thoughtfully appointed 2nd-floor condo
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
Palms at Wailea 1302! Top floor condo with Amazing Garden and Ocean Views!
Sleeps 6 · 2 bedrooms · 2 bathrooms
8.28.2 out of 10
Very goodvery good
18 reviews(18 reviews)
Wailea Ekahi 36B: Ground Floor, Lush Garden Views
Sleeps 4 · 1 bedroom · 2 bathrooms
8.48.4 out of 10
Very goodvery good
35 reviews(35 reviews)
Top rated rentals - Shops at Wailea
Great condo
1010 out of 10
Exceptionalexceptional
40 reviews(40 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