Holiday rentals near Pilates Maui

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November 2025

December 2025

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:6 Feb - 13 Feb

Exceptional

(149 reviews)

Featured on A&E's Vacation Rental Potential! Luxury Family Condo! AC and Pool!

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$1,139 per night

includes taxes & fees

Exceptional

(30 reviews)

WEK 43D Remodeled Wailea 2BD w AC Pool Near Beach

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$1,396 per night

includes taxes & fees

Exceptional

(202 reviews)

Great for families and couples. Next to a tropical pool in Hawaiian landscape.

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$903 per night

includes taxes & fees

This is our beach entry stairwell down to the beach. Need an access code.

Exceptional

(24 reviews)

October LAST Minute SPECIAL ! Direct Ocean Front Prop Wailea Ekahi 42A 1 Bed/2B

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$1,184 per night

includes taxes & fees

Dine al fresco on the furnished lanai overlooking the lush greens of Wailea's golf course

Exceptional

(21 reviews)

GC 163 2BD Wailea Condo w AC Pool Close to Beach

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$1,055 per night

includes taxes & fees

Exceptional

(95 reviews)

North Shore Guest House @ Maui Adventure Villa

Haiku, HI

8% off

for 7 nights, 1 room

AU$898 per night

includes taxes & fees

Exceptional

(200 reviews)

Maui is calling you back! Enjoy our Ocean View Cottage- 200+ Rave Reviews Await!

Kaanapali, HI

7% off

for 7 nights, 1 cottage

AU$792 per night

includes taxes & fees

Exceptional

(38 reviews)

PU 153-4 Spacious Puamana Unit & Walk To The Beach

Lahaina, HI

7% off

for 7 nights, 1 home

AU$1,284 per night

includes taxes & fees

Exceptional

(6 reviews)

Welcome to Paradise! Paia is Maui's hidden gem. Windsports, shopping, & dinning

Paia, HI

7% off

for 7 nights, 1 apartment

AU$962 per night

includes taxes & fees

You'll love the lanai which is right near the sunken pool area, creating quiet

Exceptional

(47 reviews)

Maui Kamaole, 2 lanais, queen sofa beds, quiet, eco friendly, south Kihei condo

Kihei, HI

8% off

for 7 nights, 1 apartment

AU$933 per night

includes taxes & fees

Wonderful

(32 reviews)

WE 1604 Wailea 2BD Condo w AC Pool Near Beaches

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$985 per night

includes taxes & fees

Exceptional

(17 reviews)

Beautiful Kamaole Sands Oceanview Condominium - Xmas is available!!

Kihei, HI

8% off

for 7 nights, 1 apartment

AU$741 per night

includes taxes & fees

Exceptional

(46 reviews)

OCT-Nov 2025 SPEC! 2BR/1BA BEACHFRONT - GREAT LOCATION- EXCEPTIONAL REVIEWS

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$744 per night

includes taxes & fees

Exceptional

(5 reviews)

Limited Offer! Couples Getaway! Beach, Pool, Tennis, AC. Video Tour!

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$456 per night

includes taxes & fees

That amazing ocean view from every seat in the house!

Exceptional

(49 reviews)

Oceanfront Gem, Top Floor Views & Gorgeous Sunsets, KING Bed, FULL AC, DUAL Bath Sink, FAST WiFi

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$880 per night

includes taxes & fees

Exceptional

(78 reviews)

ALII 456 OceanFront Tropical Getaway w Ocean Views

Kaanapali, HI

7% off

for 7 nights, 1 apartment

AU$2,421 per night

includes taxes & fees

Exceptional

(65 reviews)

Very popular unit top floor garden and ocean view. Hot summer deals, book now!

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$728 per night

includes taxes & fees

Exceptional

(121 reviews)

Nov 10-Dec 20 199/day OCEANFRONT walkout 1bdrm 2ba sleeps 4, pool,lawn & beach.

Lahaina, HI

7% off

for 7 nights, 1 apartment

AU$549 per night

includes taxes & fees

Exceptional

(120 reviews)

Artistic Top-Floor Tropical Penthouse – Steps to Maui’s Best Beach

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$962 per night

includes taxes & fees

Exceptional

(11 reviews)

ICC 37 Remodeled Hawaiian Cottage Near Beach wPool

Kaanapali, HI

7% off

for 7 nights, 1 apartment

AU$886 per night

includes taxes & fees

You deserve an unobstructed ocean view for your Maui vacation!

Exceptional

(184 reviews)

Ocean Front Renovated 2 BR/BA Luxury Condo w/ A/C . 2nd Floor Unobstructed View

Kihei, HI

7% off

for 7 nights, 1 apartment

AU$1,103 per night

includes taxes & fees

Exceptional

(48 reviews)

KKP 208 Renovated Condo w AC Near Beach Shops

Kihei, HI

6% off

for 7 nights, 1 apartment

AU$690 per night

includes taxes & fees

Exceptional

(57 reviews)

Beachfront condo in Maalaea - 2 Bedroom 2 Bath - Ground floor, AC!!!

Maalaea, HI

7% off

for 7 nights, 1 apartment

AU$1,063 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Pilates Maui

Showing deals for: 2 Feb - 5 Feb

Relax in comfort-watch whales from your lanai

Premier Host

Kanai A Nalu-Spectacular Whale Watching, Beachfront, Wifi & Split Air thru out

Sleeps 6 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

AU$760 per night

includes taxes & fees

Premier Host

This remodeled condo earned "Best in Kihei" 4 times and “#1 in Maui” Ocean View!

Sleeps 4 · 1 bathroom

for 3 nights, 1 apartment

AU$835 per night

includes taxes & fees

Premier Host

Historic Upcountry Maui Property With Pool, 7Bedrooms, Sleeps 16

Sleeps 16 · 7 bedrooms · 7 bathrooms

for 3 nights, 1 home

AU$3,668 per night

includes taxes & fees

JACKPOT! You just found the best unit. Custom remodel and a HDTV on Steroids!

Premier Host

Bingo! Maui Vista Favorite 170 reviews, pool front w/central split A/C.

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

AU$871 per night

includes taxes & fees

Top rated rentals - Pilates Maui

Welcome to your Private Romantic Cottage in Paradise while enjoying Maui!

Premier Host

Great retreat

Simple, clean and homely. A quiet base for exploring the island

Bo D.

Stayed July 2024

Premier Host

Perfect Stay.

This was such a great place for our family of four older children. It was so beautiful to come back to after our day of touring the island sites. We were right on the beach and could look out over to the island beyond, watch the surfers and even dolphins going by. An afternoon swim was fabulous before a cocktail on our patio. The house was very well set up with everything we needed. We cooked most nights and just enjoyed being at the house. We had great communication with the owner and everything for check in ran smoothly.

Sally Y.

Stayed June 2019

Premier Host

Wonderful property couldn't ask for better

Thank you so much Mark for sharing your beautiful condo with us you couldn't ask for better everything you needed. Amazing beach at your door and swimming with the turtles every morning was a highlight for the children. We loved everything about Makena Surf and especially B-303. Hard coming back to New Zealand's cold and wet winter. Look forward to returning one day.

Sally M.

Stayed July 2016

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More quality time
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All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
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Holiday rentals near Pilates Maui

Holiday rentals with weekly discounts - Pilates Maui

Image gallery for Featured on A&E's Vacation Rental Potential! Luxury Family Condo! AC and Pool!

Featured on A&E's Vacation Rental Potential! Luxury Family Condo! AC and Pool!

Find spaces that suit your style

Find the best place to stay - Pilates Maui

Kanai A Nalu-Spectacular Whale Watching, Beachfront, Wifi & Split Air thru out

Top rated rentals - Pilates Maui

Great retreat

Peace of mind

More quality time

All the privacy of home

More for less

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