Holiday rentals near Shops at Wailea
We found 4,677 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:18 Jul - 25 Jul
Image gallery for Hawaiian Cottage and Personal Paradise /BBKM 2013/0004

1010 out of 10 rating
Exceptional
(191 reviews)
Hawaiian Cottage and Personal Paradise /BBKM 2013/0004
Kihei, HI
7% off
Price is NZ$13,410
NZ$13,410
NZ$1,916 per night
includes taxes & fees
Image gallery for Beautiful beaches for swimming and sunsets! Kamaole Sands 3-207

9.89.8 out of 10 rating
Exceptional
(18 reviews)
Beautiful beaches for swimming and sunsets! Kamaole Sands 3-207
Kihei, HI
7% off
Price is NZ$3,609
NZ$3,609
NZ$516 per night
includes taxes & fees
Image gallery for PRIVATE HOME on a lush half acre, Kihei Oasis boasts a 40k gallon heated pool!

1010 out of 10 rating
Exceptional
(182 reviews)
PRIVATE HOME on a lush half acre, Kihei Oasis boasts a 40k gallon heated pool!
Kihei, HI
7% off
Price is NZ$11,509
NZ$11,509
NZ$1,644 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
(30 reviews)
Maui Paradise: Steps to Sand & Sun. Blg#1-Ocean View, AC's, Fast Wifi, 1st Floor
Kihei, HI
7% off
Price is NZ$4,562
NZ$4,562
NZ$652 per night
includes taxes & fees
Image gallery for Wailea Ekahi 54C: Best View & New Kitchen

1010 out of 10 rating
Exceptional
(36 reviews)
Wailea Ekahi 54C: Best View & New Kitchen
Kihei, HI
7% off
Price is NZ$8,465
NZ$8,465
NZ$1,209 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$4,304
NZ$4,304
NZ$615 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
(22 reviews)
Oceanside -Walk to Beach- Modern & Serene- 2BD, 2BA- Kihei Alii Kai-Full Remodel
Kihei, HI
7% off
Price is NZ$6,306
NZ$6,306
NZ$901 per night
includes taxes & fees
Image gallery for Maui Banyan fave! Ocean View, Renovated, Steps to the Beach, King Bed, Split AC

9.89.8 out of 10 rating
Exceptional
(148 reviews)
Maui Banyan fave! Ocean View, Renovated, Steps to the Beach, King Bed, Split AC
Kihei, HI
7% off
Price is NZ$4,304
NZ$4,304
NZ$615 per night
includes taxes & fees
Image gallery for Watch the whales from your own personal lanai!!!!

9.89.8 out of 10 rating
Exceptional
(84 reviews)
Watch the whales from your own personal lanai!!!!
Kihei, HI
7% off
Price is NZ$6,888
NZ$6,888
NZ$984 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$9,409
NZ$9,409
NZ$1,344 per night
includes taxes & fees
Image gallery for Wailea Ekahi 51F Oceanview - Walk to Beach

9.89.8 out of 10 rating
Exceptional
(94 reviews)
Wailea Ekahi 51F Oceanview - Walk to Beach
Kihei, HI
8% off
Price is NZ$4,371
NZ$4,371
NZ$624 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
(154 reviews)
Spacious 3 BR, Walk to Best Beaches & Shops in South Kihei! Sleeps 8
Kihei, HI
7% off
Price is NZ$8,977
NZ$8,977
NZ$1,282 per night
includes taxes & fees
Image gallery for 5 Star Ocean View, Beach House Chic, Click the Video tour below!

1010 out of 10 rating
Exceptional
(86 reviews)
5 Star Ocean View, Beach House Chic, Click the Video tour below!
Kihei, HI
7% off
Price is NZ$4,943
NZ$4,943
NZ$706 per night
includes taxes & fees
Image gallery for Amazing Oceanfront Views!

9.29.2 out of 10 rating
Wonderful
(5 reviews)
Amazing Oceanfront Views!
Kihei, HI
7% off
Price is NZ$6,924
NZ$6,924
NZ$989 per night
includes taxes & fees
Image gallery for Beachfront South Kihei Road ~ Royal Mauian

1010 out of 10 rating
Exceptional
(6 reviews)
Beachfront South Kihei Road ~ Royal Mauian
Kihei, HI
7% off
Price is NZ$5,151
NZ$5,151
NZ$736 per night
includes taxes & fees
Image gallery for Book Summer '25 NOW! Ocean-view, top-floor condo for 2.

9.69.6 out of 10 rating
Exceptional
(35 reviews)
Book Summer '25 NOW! Ocean-view, top-floor condo for 2.
Kihei, HI
7% off
Price is NZ$4,153
NZ$4,153
NZ$593 per night
includes taxes & fees
Image gallery for Contemporary Chic Comfy - 2Bed 2Bath Condo, Steps to Charley Young Beach

1010 out of 10 rating
Exceptional
(8 reviews)
Contemporary Chic Comfy - 2Bed 2Bath Condo, Steps to Charley Young Beach
Kihei, HI
7% off
Price is NZ$5,720
NZ$5,720
NZ$817 per night
includes taxes & fees
Image gallery for 🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean Sunsets

9.89.8 out of 10 rating
Exceptional
(138 reviews)
🌺Lush Oceanfront Penthouse with Pool, Hot Tub, Mountain Sunrises, Ocean Sunsets
Kihei, HI
7% off
Price is NZ$4,508
NZ$4,508
NZ$644 per night
includes taxes & fees
Image gallery for **Elegant Condo, Ocean Front ! Top floor 2bed&2bath.. NO ELEVATOR

9.69.6 out of 10 rating
Exceptional
(72 reviews)
**Elegant Condo, Ocean Front ! Top floor 2bed&2bath.. NO ELEVATOR
Kihei, HI
7% off
Price is NZ$3,940
NZ$3,940
NZ$563 per night
includes taxes & fees
Image gallery for Maui Kamaole I-205; 2 bedroom ocean view condo

9.69.6 out of 10 rating
Exceptional
(75 reviews)
Maui Kamaole I-205; 2 bedroom ocean view condo
Kihei, HI
7% off
Price is NZ$5,120
NZ$5,120
NZ$731 per night
includes taxes & fees
Image gallery for Wailea Ekahi6D NEWLY UPDATED 2nd Floor, Part Ocean View,1 min walk to Beach&Pool

9.89.8 out of 10 rating
Exceptional
(76 reviews)
Wailea Ekahi6D NEWLY UPDATED 2nd Floor, Part Ocean View,1 min walk to Beach&Pool
Kihei, HI
7% off
Price is NZ$6,190
NZ$6,190
NZ$884 per night
includes taxes & fees
Image gallery for Kamaole Sands Inner Courtyard - Building 1

9.49.4 out of 10 rating
Exceptional
(106 reviews)
Kamaole Sands Inner Courtyard - Building 1
Kihei, HI
7% off
Price is NZ$3,122
NZ$3,122
NZ$446 per night
includes taxes & fees
Image gallery for Romantic Maui Getaway! Direct Beach~Ocean Front! ~ Ground floor! Hotel Protected

9.49.4 out of 10 rating
Exceptional
(84 reviews)
Romantic Maui Getaway! Direct Beach~Ocean Front! ~ Ground floor! Hotel Protected
Kihei, HI
7% off
Price is NZ$4,357
NZ$4,357
NZ$622 per night
includes taxes & fees
Image gallery for Maui Oceanfront Condo with Spectacular 180 Degree Ocean View!!

9.49.4 out of 10 rating
Exceptional
(110 reviews)
Maui Oceanfront Condo with Spectacular 180 Degree Ocean View!!
Maalaea, HI
7% off
Price is NZ$2,425
NZ$2,425
NZ$346 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
702 reviews(702 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
8 reviews(8 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)
Prime Wailea Location! Split AC! Wailea Ekahi 36E
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
Perfect in every way
1010 out of 10
Exceptionalexceptional
82 reviews(82 reviews)
Great condo
1010 out of 10
Exceptionalexceptional
39 reviews(39 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