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Holiday rentals near Waihee Ridge Trail

We found 10,396 holiday rentals — enter your dates for availability

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November 2025

December 2025

If you'd like to stay close to Waihee Ridge Trail, take a look at private holiday rentals to choose your home away from home. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the amenities that you need and want, which might include parking and a washer and dryer. At the end of the day, you'll find a property to rent to meet everyone's needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Waihee Ridge Trail

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

(110 reviews)

Last minute discounts available, please ask.

Kahana, HI

8% off

for 7 nights, 1 home

AU$6,010 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

Exceptional

(67 reviews)

MODERN HAWAII ⛳️ Modern Remodel, steps to the Beach, 4th Tee, Ocean View, 4 Pools

Kapalua, HI

7% off

for 7 nights, 1 villa

AU$1,922 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

(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

Exceptional

(12 reviews)

NP B37 Relax Recharge Whale Watch OceanFront 2BD

Napili, HI

7% off

for 7 nights, 1 apartment

AU$1,452 per night

includes taxes & fees

Exceptional

(9 reviews)

RK 909 OceanFront Condo w Beautiful Ocean Views

Kahana, HI

7% off

for 7 nights, 1 apartment

AU$699 per night

includes taxes & fees

Wonderful

(77 reviews)

Ocean Front Napili Point C25 Great Views Turtles Whales & Sunsets from Lanai A/C

Napili, HI

7% off

for 7 nights, 1 apartment

AU$1,133 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

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

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

(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

Kapalua Ridge Villas 1612 ocean view lanai 1

Wonderful

(10 reviews)

KRV 1612 Remodeled Kapalua Villa w Ocean Views

Kapalua, HI

7% off

for 7 nights, 1 apartment

AU$1,407 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

Find spaces that suit your style

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Condo/Apartment

Find properties near top attractions in Waihee Ridge Trail

Waihee Ridge Trail

Find the best place to stay - Waihee Ridge Trail

Showing deals for: 2 Feb - 5 Feb

The use of natural tones and textures creates a warm, welcoming environment. Kapalua Golf Villas offer elegant design that feels like home.

Premier Host

KBM Resorts | FREE CAR | Kapalua Golf Villa | 2-Bedroom Condo with Fairway views! KGV-16P3

Sleeps 4 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

AU$1,634 per night

includes taxes & fees

Imagine yourself sipping a warm cup of coffee or enjoying a nice glass of wine with this lovely view from your personal lanai!

Premier Host

Coral Cove-Poolside Condo and Panoramic Ocean View

Sleeps 7 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 apartment

AU$887 per night

includes taxes & fees

Top rated rentals - Waihee Ridge Trail

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

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
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Holiday rentals near Waihee Ridge Trail

Holiday rentals with weekly discounts - Waihee Ridge Trail

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 properties near top attractions in Waihee Ridge Trail

Map Attractions

Waihee Ridge Trail

Find the best place to stay - Waihee Ridge Trail

KBM Resorts | FREE CAR | Kapalua Golf Villa | 2-Bedroom Condo with Fairway views! KGV-16P3

Top rated rentals - Waihee Ridge Trail

Great retreat

Peace of mind

More quality time

All the privacy of home

More for less

Holiday Rental options near Waihee Ridge Trail

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