Holiday rentals near The Skyline Trail

We found 3,293 holiday rentals — enter your dates for availability

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May 2026

June 2026

Holiday rentals with weekly discounts - The Skyline Trail

Showing deals for:7 Aug - 14 Aug

Exceptional

(22 reviews)

Maui Tropical Paradise - Vacation Home In Haiku - Pool/Spa

Haiku

15% off

for 7 nights, 1 home

NZ$1,543 per night

includes taxes & fees

Exceptional

(92 reviews)

Private, Luxurious Dream Home with Swimming Pool, Permitted

Haiku

7% off

for 7 nights, 1 home

NZ$2,193 per night

includes taxes & fees

Exceptional

(199 reviews)

Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath

Hana

7% off

for 7 nights, 1 cottage

NZ$618 per night

includes taxes & fees

Jasmine Suite living room with panoramic ocean view

Exceptional

(153 reviews)

360 Degree Ocean And Mountain Views From This Stunning Home.

Hana

8% off

for 7 nights, 1 home

NZ$662 per night

includes taxes & fees

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

Exceptional

(34 reviews)

LUXURIOUS Wailea BEACH Direct Ocean Front Property Wailea Ekahi 42A 1 Bed/2B

Kihei

7% off

for 7 nights, 1 apartment

NZ$1,001 per night

includes taxes & fees

Stunning views from entire dining/living area

Exceptional

(18 reviews)

Breathtaking Ocean Views! Beach Front Luxury Penthouse, Polo Beach 2 Bed/2 Bath

Kihei

7% off

for 7 nights, 1 apartment

NZ$2,581 per night

includes taxes & fees

Exceptional

(48 reviews)

Ekahi 27A: Priceless Ocean View from a Private Lanai

Kihei

22% off

for 7 nights, 1 apartment

NZ$731 per night

includes taxes & fees

Exceptional

(47 reviews)

Beachfront 1-bedroom corner condo on Kameole Beach II, with two ocean views.

Kihei

7% off

for 7 nights, 1 apartment

NZ$738 per night

includes taxes & fees

Wonderful

(13 reviews)

Charming Studio at Maui Banyan Resort - Walk to Beach, Pools, AC, Beach Gear

Kihei

7% off

for 7 nights, 1 room

NZ$423 per night

includes taxes & fees

Exceptional

(94 reviews)

Fabulous Ocean Views, Steps From Polo Beach, Luxury 2 Bed 2 Bath

Kihei

7% off

for 7 nights, 1 apartment

NZ$1,695 per night

includes taxes & fees

Exceptional

(159 reviews)

Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed

Kihei

7% off

for 7 nights, 1 apartment

NZ$560 per night

includes taxes & fees

Exceptional

(96 reviews)

1BEDROOM/2BATH Downstairs Condo in Wailea Ekahi Village #46A -- Locally Owned

Kihei

7% off

for 7 nights, 1 apartment

NZ$726 per night

includes taxes & fees

Lanai for outdoor dining and with perfect view for turtle or whale watching.

Exceptional

(48 reviews)

Breathtaking Ocean Front Views. Incredible Reviews.

Kihei

7% off

for 7 nights, 1 apartment

NZ$1,595 per night

includes taxes & fees

Exceptional

(102 reviews)

Unobstructed Views – Prime Location - Steps To Beach - Newly Renovated

Kihei

7% off

for 7 nights, 1 apartment

NZ$626 per night

includes taxes & fees

Exceptional

(26 reviews)

Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo

Kihei

8% off

for 7 nights, 1 apartment

NZ$2,957 per night

includes taxes & fees

Exceptional

(166 reviews)

Wailea 1 BR Condo, close to everything, good pricing

Kihei

7% off

for 7 nights, 1 apartment

NZ$545 per night

includes taxes & fees

Exceptional

(31 reviews)

Maui Vista #2109 Ground Floor! Reduced rates! AC in bdrm & LR, steps to beach!!

Kihei

7% off

for 7 nights, 1 apartment

NZ$391 per night

includes taxes & fees

Exceptional

(140 reviews)

BEACH LUX VILLA with AWESOME VIEW! CLICK on “About this Property” for a TOUR!

Kihei

7% off

for 7 nights, 1 apartment

NZ$704 per night

includes taxes & fees

Exceptional

(179 reviews)

Read our Reviews! Newly Updated Condo! Perfect Getaway Steps to Beach & Dining!

Kihei

7% off

for 7 nights, 1 apartment

NZ$411 per night

includes taxes & fees

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Find the best place to stay - The Skyline Trail

Premier Host

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002

Sleeps 4 · 1 bedroom · 1 bathroom

Premier Host

AUTHENTIC HAWAIIAN BEACH HOUSE ON HANA BAY. 5-minute walk to beaches and town.

Sleeps 2 · 1 bedroom · 1 bathroom

Top rated rentals - The Skyline Trail

Image of Lovely Tropical Retreat! Spotless and amazingly well equipped. Great rates.

All you need

Well equipped with toiletries, comprehensive kitchen for self-catering with a large fridge-freezer. A large range of cooking utensils & dishes as well as plastic containers & bags, foil, clingfilm etc. Fantastic beach equipment including child life jacket, beach umbrella & chairs, snorkel & fins, cooler bin with icepacks, and even a boogie board. Quiet location despite a main road nearby - we slept so well & were never disturbed by people or traffic going by. So nice to get a phone call from the owner on our first evening, making sure we'd settled in OK. Very comfortable bed, pillows, & air mattress with bedding for our 5 year old. We totally recommend Nancy & Stafford's condo in Kihei.

Fiona H.

Stayed Jun 2025

Image of Luxe Oceanview Hideaway on Wailea Old Blue Golf Course

Premier Host

Perfect piece of paradise

Great location and a very clean and comfortable unit in Wailea. I would absolutely stay again! Thanks for sharing your beautiful condo with us!

Kelsey L.

Stayed Aug 2022

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