Holiday rentals near Pilates Maui
We found 6,908 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Pilates Maui, take a look at private holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with your children or with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and garden. Whatever you're looking for, you'll be sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Pilates Maui
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 "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 Newly Remodeled 1BR-just steps to the beach!
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Newly Remodeled 1BR-just steps to the beach!
Kaanapali, HI
7% off
Price is AU$4,940
AU$4,940
AU$706 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 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 Breathtaking views of Kaanapali Beach, Black Rock and the island of Molokai.
1010 out of 10 rating
Exceptional
(49 reviews)
Breathtaking views of Kaanapali Beach, Black Rock and the island of Molokai.
Kaanapali, HI
16% off
Price is AU$7,032
AU$7,032
AU$1,005 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 Westin Kaanapali Oceanfront Resort, Great Studio, Sleeps Four....$400/N
9.69.6 out of 10 rating
Exceptional
(17 reviews)
Westin Kaanapali Oceanfront Resort, Great Studio, Sleeps Four....$400/N
Kaanapali, HI
8% off
Price is AU$4,957
AU$4,957
AU$708 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 A403 - 1 Bedroom Fully Remodeled
9.89.8 out of 10 rating
Exceptional
(123 reviews)
A403 - 1 Bedroom Fully Remodeled
Kaanapali, HI
7% off
Price is AU$4,945
AU$4,945
AU$706 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Pilates Maui
Showing deals for: 13 Sept - 16 Sept
Maui Beach Vacation Club
Sleeps 4 · 1 bedroom
8.28.2 out of 10
Very goodvery good
754 reviews(754 reviews)
The current price is AU$1,396
AU$1,396
for 3 nights, 1 room
AU$465 per night
includes taxes & fees
Beach Boho 2 Min Walk To Cove and CYB!
Sleeps 6 · 1 bedroom · 1 bathroom
The current price is AU$1,402
AU$1,402
for 3 nights, 1 home
AU$467 per night
includes taxes & fees
Stunning Oceanview * Oceanfront 2/ 2 Bath Prime Location
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
The current price is AU$2,511
AU$2,511
for 3 nights, 1 apartment
AU$837 per night
includes taxes & fees
Charming 4 Rooms Steps from the Beach w/ Poolside Drinks Lounge | Pet-friendly
Sleeps 16 · 4 bedrooms · 4 bathrooms
The current price is AU$6,008
AU$6,008
for 3 nights, 1 home
AU$2,003 per night
includes taxes & fees
Menehune Shores #220 – Beachside Bliss with Panoramic Ocean Views
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
20 reviews(20 reviews)
The current price is AU$3,250
AU$3,250
for 3 nights, 1 apartment
AU$1,083 per night
includes taxes & fees
Oceanfront Studio #102 at Kauhale Makai Beach Activities and Comfort Await!
Sleeps 4 · 1 bathroom
8.68.6 out of 10
Excellentexcellent
21 reviews(21 reviews)
The current price is AU$1,440
AU$1,440
for 3 nights, 1 apartment
AU$480 per night
includes taxes & fees
Top rated rentals - Pilates Maui
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