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 NZ$6,926
NZ$6,926
NZ$989 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$7,376
NZ$7,376
NZ$1,054 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$4,332
NZ$4,332
NZ$619 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 NZ$5,344
NZ$5,344
NZ$763 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$4,437
NZ$4,437
NZ$634 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$23,916
NZ$23,916
NZ$3,417 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$6,660
NZ$6,660
NZ$951 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
15% off
Price is NZ$7,750
NZ$7,750
NZ$1,107 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$5,448
NZ$5,448
NZ$778 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$3,048
NZ$3,048
NZ$435 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 NZ$5,362
NZ$5,362
NZ$766 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$2,198
NZ$2,198
NZ$314 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$5,012
NZ$5,012
NZ$716 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$9,028
NZ$9,028
NZ$1,290 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
18% off
Price is NZ$3,736
NZ$3,736
NZ$534 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$11,309
NZ$11,309
NZ$1,616 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$4,068
NZ$4,068
NZ$581 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$4,415
NZ$4,415
NZ$631 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$8,688
NZ$8,688
NZ$1,241 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$5,138
NZ$5,138
NZ$734 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$12,546
NZ$12,546
NZ$1,792 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$2,481
NZ$2,481
NZ$354 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$8,105
NZ$8,105
NZ$1,158 per night
includes taxes & fees
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Find the best place to stay - Pilates Maui
Maui Beach Vacation Club
Sleeps 4 · 1 bedroom
8.28.2 out of 10
Very goodvery good
754 reviews(754 reviews)
Beachfront Resort - Ground Floor - Corner Unit - Steps to the Beach-Pool-Spa!
Sleeps 4 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
41 reviews(41 reviews)
Beach Boho 2 Min Walk To Cove and CYB!
Sleeps 6 · 1 bedroom · 1 bathroom
Tranquil 2-bedroom condo with AC, in Kihei. Steps from the Beach!
Sleeps 4 · 2 bedrooms · 1 bathroom
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)
Charming 4 Rooms Steps from the Beach w/ Poolside Drinks Lounge | Pet-friendly
Sleeps 16 · 4 bedrooms · 4 bathrooms
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