Holiday rentals near Shops at Wailea
We found 4,721 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:19 Sept - 26 Sept
Image gallery for Wailea Ekahi 54A: Completely Remodeled & Panoramic Ocean View
1010 out of 10 rating
Exceptional
(84 reviews)
Wailea Ekahi 54A: Completely Remodeled & Panoramic Ocean View
Kihei, HI
11% off
Price is AU$6,417
AU$6,417
AU$917 per night
includes taxes & fees
Image gallery for Enjoy Sun Rise over Volcano & Sunset over Ocean from our Lanai! BEST VIEWS!!
1010 out of 10 rating
Exceptional
(126 reviews)
Enjoy Sun Rise over Volcano & Sunset over Ocean from our Lanai! BEST VIEWS!!
Kihei, HI
7% off
Price is AU$6,844
AU$6,844
AU$978 per night
includes taxes & fees
Image gallery for Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo
Kihei, HI
8% off
Price is AU$14,476
AU$14,476
AU$2,068 per night
includes taxes & fees
Image gallery for "ALOHA" Ocean View Maui Kamaole Condo in South Maui
1010 out of 10 rating
Exceptional
(78 reviews)
"ALOHA" Ocean View Maui Kamaole Condo in South Maui
Kihei, HI
11% off
Price is AU$3,998
AU$3,998
AU$571 per night
includes taxes & fees
Image gallery for Just Steps to Kamaole III Beach!!!
1010 out of 10 rating
Exceptional
(127 reviews)
Just Steps to Kamaole III Beach!!!
Kihei, HI
7% off
Price is AU$4,401
AU$4,401
AU$629 per night
includes taxes & fees
Image gallery for Escape to Paradise – Your Dream Wailea Getaway Awaits!
9.89.8 out of 10 rating
Exceptional
(94 reviews)
Escape to Paradise – Your Dream Wailea Getaway Awaits!
Kihei, HI
7% off
Price is AU$4,093
AU$4,093
AU$585 per night
includes taxes & fees
Image gallery for Very popular unit top floor garden and ocean view. Hot summer deals, book now!
9.89.8 out of 10 rating
Exceptional
(61 reviews)
Very popular unit top floor garden and ocean view. Hot summer deals, book now!
Kihei, HI
7% off
Price is AU$3,920
AU$3,920
AU$560 per night
includes taxes & fees
Image gallery for DIRECT BEACHFRONT WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS 4Bd 3BA 3892 s.f.
1010 out of 10 rating
Exceptional
(112 reviews)
DIRECT BEACHFRONT WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS 4Bd 3BA 3892 s.f.
Kihei, HI
8% off
Price is AU$21,221
AU$21,221
AU$3,032 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
14% off
Price is AU$6,166
AU$6,166
AU$881 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
(24 reviews)
Oceanside -Walk to Beach- Modern & Serene- 2BD, 2BA- Kihei Alii Kai-Full Remodel
Kihei, HI
7% off
Price is AU$5,038
AU$5,038
AU$720 per night
includes taxes & fees
Image gallery for BEST VALUE! Partial Ocean View-Prime location-Steps to Kam II Beach-Redecorated
9.49.4 out of 10 rating
Exceptional
(127 reviews)
BEST VALUE! Partial Ocean View-Prime location-Steps to Kam II Beach-Redecorated
Kihei, HI
7% off
Price is AU$2,813
AU$2,813
AU$402 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
13% off
Price is AU$2,064
AU$2,064
AU$295 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 AU$4,632
AU$4,632
AU$662 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
(87 reviews)
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Kihei, HI
7% off
Price is AU$8,197
AU$8,197
AU$1,171 per night
includes taxes & fees
Image gallery for 20%off 7days! Ocean View Top Floor, Steps from Beach, AC all rooms, Pool, Tennis
9.89.8 out of 10 rating
Exceptional
(141 reviews)
20%off 7days! Ocean View Top Floor, Steps from Beach, AC all rooms, Pool, Tennis
Kihei, HI
19% off
Price is AU$3,443
AU$3,443
AU$492 per night
includes taxes & fees
Image gallery for Luxurious Wailea Polo Beach Club Oceanfront Condo, Spectaular View
9.69.6 out of 10 rating
Exceptional
(84 reviews)
Luxurious Wailea Polo Beach Club Oceanfront Condo, Spectaular View
Kihei, HI
8% off
Price is AU$10,552
AU$10,552
AU$1,507 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 AU$3,752
AU$3,752
AU$536 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
5% off
Price is AU$4,072
AU$4,072
AU$582 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
(156 reviews)
Spacious 3 BR, Walk to Best Beaches & Shops in South Kihei! Sleeps 8
Kihei, HI
8% off
Price is AU$7,888
AU$7,888
AU$1,127 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 AU$4,748
AU$4,748
AU$678 per night
includes taxes & fees
Image gallery for Beachfront Platinum Condo, Makena Surf. 15% off till 7/31 due to construction.
1010 out of 10 rating
Exceptional
(50 reviews)
Beachfront Platinum Condo, Makena Surf. 15% off till 7/31 due to construction.
Kihei, HI
8% off
Price is AU$11,235
AU$11,235
AU$1,605 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 AU$2,319
AU$2,319
AU$331 per night
includes taxes & fees
Image gallery for Largest Two Bedroom/ Two Bath in the Village, Sleeps Eight & Close to the Beach
9.89.8 out of 10 rating
Exceptional
(179 reviews)
Largest Two Bedroom/ Two Bath in the Village, Sleeps Eight & Close to the Beach
Kihei, HI
14% off
Price is AU$7,355
AU$7,355
AU$1,051 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Shops at Wailea
Showing deals for: 13 Sept - 16 Sept
Wailea Serenity | 2 Bed, 2 Bath
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
36 reviews(36 reviews)
The current price is AU$1,484
AU$1,484
for 3 nights, 1 apartment
AU$495 per night
includes taxes & fees
Wailea Grand Champions - CoralTree Residence Collection
Sleeps 4 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
719 reviews(719 reviews)
The current price is AU$2,415
AU$2,415
for 3 nights, 1 apartment
AU$805 per night
includes taxes & fees
Spacious, thoughtfully appointed 2nd-floor condo
Sleeps 6 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
The current price is AU$2,054
AU$2,054
for 3 nights, 1 apartment
AU$685 per night
includes taxes & fees
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)
The current price is AU$2,455
AU$2,455
for 3 nights, 1 apartment
AU$818 per night
includes taxes & fees
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)
The current price is AU$2,280
AU$2,280
for 3 nights, 1 apartment
AU$760 per night
includes taxes & fees
Ground-level Wailea condo with golf views
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
20 reviews(20 reviews)
The current price is AU$2,091
AU$2,091
for 3 nights, 1 apartment
AU$697 per night
includes taxes & fees
Top rated rentals - Shops at Wailea
Kihei
1010 out of 10
Exceptionalexceptional
200 reviews(200 reviews)
Wonderful property couldn't ask for better
1010 out of 10
Exceptionalexceptional
90 reviews(90 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