Holiday rentals near The Skyline Trail

We found 3,343 holiday rentals — enter your dates for availability

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February 2026

March 2026

Choose the right holiday rental that's near The Skyline Trail. Holiday homes provide the amenities that you need and want for your family, friends or furry companion, such as Wi-Fi and a washer and dryer. No matter what you're looking for, you'll be able to choose a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - The Skyline Trail

Showing deals for:15 May - 22 May

Wonderful

(12 reviews)

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

Kihei

7% off

for 7 nights, 1 room

NZ$324 per night

includes taxes & fees

Exceptional

(43 reviews)

Ekahi 27A: Priceless Ocean View from a Private Lanai

Kihei

7% off

for 7 nights, 1 apartment

NZ$854 per night

includes taxes & fees

Cozy Hana Bay View Cottage with covered lanai, new vinyl decking and siding.

Exceptional

(193 reviews)

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

Hana

7% off

for 7 nights, 1 cottage

NZ$615 per night

includes taxes & fees

Cottage and pool area with surrounding tropical foliage

Exceptional

(153 reviews)

Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted

Kihei

7% off

for 7 nights, 1 cottage

NZ$985 per night

includes taxes & fees

Master bedroom #1 king bed with eqyptian cotton linens

Exceptional

(138 reviews)

Hula On In to Beach House Chic Style, Click the Video tour below!

Wailea

7% off

for 7 nights, 1 villa

NZ$886 per night

includes taxes & fees

Beautifully updated living area with wood floors

Excellent

(60 reviews)

BEST RATES in Low Season!~Never a better time to make a trip to Paradise!!

Kihei

7% off

for 7 nights, 1 apartment

NZ$423 per night

includes taxes & fees

Wonderful

(5 reviews)

Escape to Serenity – Oceanview 1 Bedroom 2 Bath at Wailea Ekahi 48-E, Sleeps 4

Kihei

7% off

for 7 nights, 1 apartment

NZ$960 per night

includes taxes & fees

Wonderful

(150 reviews)

Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b

Hana

7% off

for 7 nights, 1 home

NZ$733 per night

includes taxes & fees

Jasmine Suite living room with panoramic ocean view

Exceptional

(150 reviews)

360 Degree Ocean And Mountain Views From This Stunning Home.

Hana

8% off

for 7 nights, 1 home

NZ$656 per night

includes taxes & fees

Entertainment Room with beautiful view of the ocean

Exceptional

(92 reviews)

Luxury Vacation Rental in Wailea Beachfront - Exclusive Polo Beach Location

Kihei

8% off

for 7 nights, 1 apartment

NZ$1,517 per night

includes taxes & fees

Exceptional

(24 reviews)

Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo

Wailea-Makena

8% off

for 7 nights, 1 apartment

NZ$2,243 per night

includes taxes & fees

Exceptional

(119 reviews)

Luxury Wailea Condo - Incredible Ocean Views! 5 Star Reviews. Multi Zone AC.

Wailea, Maui

7% off

for 7 nights, 1 apartment

NZ$1,066 per night

includes taxes & fees

Exceptional

(32 reviews)

March openings! Beautiful oceanview Kamaole Sands 2-206

Kihei

7% off

for 7 nights, 1 apartment

NZ$660 per night

includes taxes & fees

Exceptional

(26 reviews)

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

Kihei

7% off

for 7 nights, 1 apartment

NZ$461 per night

includes taxes & fees

Exceptional

(109 reviews)

Spectacular ocean and beach view 2 BR condo, steps from the ocean!

Kihei

7% off

for 7 nights, 1 apartment

NZ$793 per night

includes taxes & fees

Excellent

(40 reviews)

~Amazing Ocean View on 3rd flr~ MAUI AWAITS YOU!!

Kihei

7% off

for 7 nights, 1 apartment

NZ$490 per night

includes taxes & fees

Exceptional

(93 reviews)

Aloha! Close enough to the beach you can walk. Maui misses you!

Kihei

7% off

for 7 nights, 1 apartment

NZ$576 per night

includes taxes & fees

Exceptional

(29 reviews)

Oceanside -Walk to Beach- Modern & Serene- 2BD, 2BA- Kihei Alii Kai-Full Remodel

Kihei

7% off

for 7 nights, 1 apartment

NZ$879 per night

includes taxes & fees

3 bed/2 bath double suite rental. View of lanai from the backyard.

Exceptional

(31 reviews)

Hana Bay View 3 BR/2 BA house sleeps 6 comfortably with 2 patios.

Hana

7% off

for 7 nights, 1 home

NZ$1,037 per night

includes taxes & fees

Exceptional

(80 reviews)

Ekahi 29C, Ocean View, Steps away from the pool

Wailea

7% off

for 7 nights, 1 apartment

NZ$1,103 per night

includes taxes & fees

You won't want to leave your Maui paradise . . . . on the lanai!

Exceptional

(111 reviews)

Direct Oceanfront/Beachfront Luxury! Recently Remodeled

Kihei

7% off

for 7 nights, 1 apartment

NZ$1,455 per night

includes taxes & fees

Find spaces that suit your style

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Condo/Apartment

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

1 bedroom · 1 bathroom

Premier Host

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

1 bedroom · 1 bathroom

Top rated rentals - The Skyline Trail

Wailea Ekolu

Gorgeous condo. Lovely and quiet. Well furnished and stocked. Fantastic sunset views. We thoroughly enjoyed our stay. Can't wait to return

Sharyn v.

Stayed Jul 2023

Image of Luxury Cottage w/ Private Pool. Under The Warm Maui Sun Pmt #BBKM\2016\0004

Premier Host

Peace, quiet and comfort.

The Villa Paola was ideal for me travelling alone - if anything it was probably more than I needed but it had all the conveniences and the environment that I required. I will definitely be sharing my memories of this Villa with friends and family. Thank you Marcello for a wonderful stay.

Michael T.

Stayed Sept 2022

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