Holiday rentals near Shops at Wailea
We found 4,722 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 NZ$6,909
NZ$6,909
NZ$987 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 NZ$7,635
NZ$7,635
NZ$1,091 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 NZ$16,234
NZ$16,234
NZ$2,319 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 NZ$4,322
NZ$4,322
NZ$617 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 NZ$4,765
NZ$4,765
NZ$681 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 NZ$4,426
NZ$4,426
NZ$632 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 NZ$23,857
NZ$23,857
NZ$3,408 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 NZ$6,644
NZ$6,644
NZ$949 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 NZ$5,434
NZ$5,434
NZ$776 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 NZ$3,041
NZ$3,041
NZ$434 per night
includes taxes & fees
Image gallery for Remodeled 2BR Condo with Lanai, Pool, and Walkable Beach Access
9.49.4 out of 10 rating
Exceptional
(158 reviews)
Remodeled 2BR Condo with Lanai, Pool, and Walkable Beach Access
Kihei, HI
7% off
Price is NZ$3,844
NZ$3,844
NZ$549 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 NZ$2,192
NZ$2,192
NZ$313 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 NZ$9,006
NZ$9,006
NZ$1,287 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
(142 reviews)
20%off 7days! Ocean View Top Floor, Steps from Beach, AC all rooms, Pool, Tennis
Kihei, HI
19% off
Price is NZ$4,003
NZ$4,003
NZ$572 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
18% off
Price is NZ$3,712
NZ$3,712
NZ$530 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 NZ$11,281
NZ$11,281
NZ$1,612 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$4,057
NZ$4,057
NZ$580 per night
includes taxes & fees
Image gallery for Aloha! Close enough to the beach you can walk. Maui misses you!
9.89.8 out of 10 rating
Exceptional
(92 reviews)
Aloha! Close enough to the beach you can walk. Maui misses you!
Kihei, HI
7% off
Price is NZ$3,742
NZ$3,742
NZ$535 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 NZ$4,404
NZ$4,404
NZ$629 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
7% off
Price is NZ$8,667
NZ$8,667
NZ$1,238 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
7% off
Price is NZ$12,515
NZ$12,515
NZ$1,788 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$5,125
NZ$5,125
NZ$732 per night
includes taxes & fees
Image gallery for Wailea Elua 803 - Ocean Views, Modern Renovation, Central AC, Wi-Fi, BBQ Grill
1010 out of 10 rating
Exceptional
(48 reviews)
Wailea Elua 803 - Ocean Views, Modern Renovation, Central AC, Wi-Fi, BBQ Grill
Kihei, Hawaii
7% off
Price is NZ$13,941
NZ$13,941
NZ$1,992 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 NZ$8,085
NZ$8,085
NZ$1,155 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
9.69.6 out of 10
Exceptionalexceptional
37 reviews(37 reviews)
Grand Champions #147 Golf Course Views Full Kitchen AC Throughout
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Wailea Grand Champions - CoralTree Residence Collection
Sleeps 4 · 1 bedroom · 1 bathroom
9.09.0 out of 10
Wonderfulwonderful
720 reviews(720 reviews)
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 place!
1010 out of 10
Exceptionalexceptional
21 reviews(21 reviews)
Perfect!
1010 out of 10
Exceptionalexceptional
127 reviews(127 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