
Holiday rentals near The Skyline Trail
We found 3,339 holiday rentals — enter your dates for availability
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:13 Mar - 20 Mar
Image gallery for Maui Banyan king, 2 bathroom, steps to Kamaole beach, sleeps 4 - No parking fee

1010 out of 10, Exceptional, (78 reviews)
Exceptional
(78 reviews)
Maui Banyan king, 2 bathroom, steps to Kamaole beach, sleeps 4 - No parking fee
Kihei, HI
7% off
Price is AU$3,883
AU$3,883
for 7 nights, 1 apartment
AU$555 per night
includes taxes & fees
Image gallery for Great for families and couples. Next to a tropical pool in Hawaiian landscape.

9.69.6 out of 10, Exceptional, (203 reviews)
Exceptional
(203 reviews)
Great for families and couples. Next to a tropical pool in Hawaiian landscape.
Kihei, HI
7% off
Price is AU$5,376
AU$5,376
for 7 nights, 1 apartment
AU$768 per night
includes taxes & fees
Image gallery for Ekahi 27A: Priceless Ocean View from a Private Lanai

1010 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)
Ekahi 27A: Priceless Ocean View from a Private Lanai
Kihei, HI
7% off
Price is AU$6,914
AU$6,914
for 7 nights, 1 apartment
AU$988 per night
includes taxes & fees
Image gallery for Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere

1010 out of 10, Exceptional, (89 reviews)
Exceptional
(89 reviews)
Direct Beach Access - Best Location - Wailea Beach Villas H101 - Walk Everywhere
Kihei, HI
8% off
Price is AU$18,294
AU$18,294
for 7 nights, 1 villa
AU$2,613 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, Exceptional, (93 reviews)
Exceptional
(93 reviews)
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Kihei, HI
7% off
Price is AU$10,611
AU$10,611
for 7 nights, 1 home
AU$1,516 per night
includes taxes & fees
Image gallery for BEST RATES in Low Season!~Never a better time to make a trip to Paradise!!

8.88.8 out of 10, Excellent, (59 reviews)
Excellent
(59 reviews)
BEST RATES in Low Season!~Never a better time to make a trip to Paradise!!
Kihei, HI
7% off
Price is AU$3,005
AU$3,005
for 7 nights, 1 apartment
AU$429 per night
includes taxes & fees
Image gallery for Breathtaking Ocean Front Views. Incredible Reviews.

1010 out of 10, Exceptional, (41 reviews)
Exceptional
(41 reviews)
Breathtaking Ocean Front Views. Incredible Reviews.
Kihei, HI
7% off
Price is AU$11,616
AU$11,616
for 7 nights, 1 apartment
AU$1,659 per night
includes taxes & fees
Image gallery for Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed

1010 out of 10, Exceptional, (150 reviews)
Exceptional
(150 reviews)
Kamaole Sands Remodeled 1 Bed 2 bathroom, Split AC, king bed
Kihei, HI
7% off
Price is AU$4,991
AU$4,991
for 7 nights, 1 apartment
AU$713 per night
includes taxes & fees
Image gallery for Maui Banyan fave! Ocean View, Renovated, Steps to the Beach, King Bed, Split AC

9.89.8 out of 10, Exceptional, (157 reviews)
Exceptional
(157 reviews)
Maui Banyan fave! Ocean View, Renovated, Steps to the Beach, King Bed, Split AC
Kihei, HI
7% off
Price is AU$4,121
AU$4,121
for 7 nights, 1 apartment
AU$589 per night
includes taxes & fees
Image gallery for Experience Maui in Comfort!! ~Fully Furnished 1b/2b Recently Updated Condo

9.89.8 out of 10, Exceptional, (31 reviews)
Exceptional
(31 reviews)
Experience Maui in Comfort!! ~Fully Furnished 1b/2b Recently Updated Condo
Kihei, HI
9% off
Price is AU$4,073
AU$4,073
for 7 nights, 1 apartment
AU$582 per night
includes taxes & fees
Image gallery for ~Amazing Ocean View on 3rd flr~ MAUI AWAITS YOU!!

8.88.8 out of 10, Excellent, (39 reviews)
Excellent
(39 reviews)
~Amazing Ocean View on 3rd flr~ MAUI AWAITS YOU!!
Kihei, HI
9% off
Price is AU$3,293
AU$3,293
for 7 nights, 1 apartment
AU$470 per night
includes taxes & fees
Image gallery for Fully Remodeled Modern Island Style!

1010 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)
Fully Remodeled Modern Island Style!
Kihei, HI
7% off
Price is AU$10,561
AU$10,561
for 7 nights, 1 apartment
AU$1,509 per night
includes taxes & fees
Image gallery for Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225

9.69.6 out of 10, Exceptional, (69 reviews)
Exceptional
(69 reviews)
Wailea Grand Champions. Walk to shops, dining & golf. Nice Ocean View. From 225
Kihei, HI
7% off
Price is AU$4,441
AU$4,441
for 7 nights, 1 apartment
AU$634 per night
includes taxes & fees
Image gallery for 5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View!

1010 out of 10, Exceptional, (235 reviews)
Exceptional
(235 reviews)
5-Star Reviews! All Remodeled! Split Air! Quiet Building 5! Ocean/Garden View!
Kihei, HI
7% off
Price is AU$4,393
AU$4,393
for 7 nights, 1 apartment
AU$628 per night
includes taxes & fees
Image gallery for Temp.Aug. sp Pro Design Ground fl. Lovey flower gardens Sleeps 6 .

9.69.6 out of 10, Exceptional, (220 reviews)
Exceptional
(220 reviews)
Temp.Aug. sp Pro Design Ground fl. Lovey flower gardens Sleeps 6 .
Kihei, HI
7% off
Price is AU$5,209
AU$5,209
for 7 nights, 1 apartment
AU$744 per night
includes taxes & fees
Image gallery for Tropical getaway at the Maui Banyan! Partial Ocean View 1 bedroom, 2 bath.

9.09.0 out of 10, Wonderful, (40 reviews)
Wonderful
(40 reviews)
Tropical getaway at the Maui Banyan! Partial Ocean View 1 bedroom, 2 bath.
Kihei, HI
9% off
Price is AU$3,354
AU$3,354
for 7 nights, 1 apartment
AU$479 per night
includes taxes & fees
Image gallery for Ocean View Condo Across from Best Beach in Maui (Kamaole Beach Royale 202)

8.68.6 out of 10, Excellent, (14 reviews)
Excellent
(14 reviews)
Ocean View Condo Across from Best Beach in Maui (Kamaole Beach Royale 202)
Kihei, HI
7% off
Price is AU$5,288
AU$5,288
for 7 nights, 1 apartment
AU$755 per night
includes taxes & fees
Image gallery for Island Surf, 612B, Kihei, Maui, Hawaii. Across the street from the beach.

9.49.4 out of 10, Exceptional, (141 reviews)
Exceptional
(141 reviews)
Island Surf, 612B, Kihei, Maui, Hawaii. Across the street from the beach.
Kihei, HI
8% off
Price is AU$2,787
AU$2,787
for 7 nights, 1 apartment
AU$398 per night
includes taxes & fees
Image gallery for Upgraded unit with Panoramic Ocean and Mountain Views

9.89.8 out of 10, Exceptional, (106 reviews)
Exceptional
(106 reviews)
Upgraded unit with Panoramic Ocean and Mountain Views
Kihei, HI
7% off
Price is AU$5,426
AU$5,426
for 7 nights, 1 apartment
AU$775 per night
includes taxes & fees
Image gallery for Fall/winter specials! Enjoy Maui for less!

9.69.6 out of 10, Exceptional, (125 reviews)
Exceptional
(125 reviews)
Fall/winter specials! Enjoy Maui for less!
Kihei, HI
7% off
Price is AU$3,918
AU$3,918
for 7 nights, 1 apartment
AU$560 per night
includes taxes & fees
Image gallery for Mana Kai Maui Condo - Right on the Beach!

9.69.6 out of 10, Exceptional, (241 reviews)
Exceptional
(241 reviews)
Mana Kai Maui Condo - Right on the Beach!
Kihei, HI
8% off
Price is AU$9,299
AU$9,299
for 7 nights, 1 apartment
AU$1,328 per night
includes taxes & fees
Image gallery for 3 minute walk to beach in South Maui!

9.89.8 out of 10, Exceptional, (129 reviews)
Exceptional
(129 reviews)
3 minute walk to beach in South Maui!
Kihei, HI
7% off
Price is AU$4,408
AU$4,408
for 7 nights, 1 apartment
AU$630 per night
includes taxes & fees
Image gallery for Your Hawaiian Beach Get Away, Steps From Great Beach!

9.69.6 out of 10, Exceptional, (102 reviews)
Exceptional
(102 reviews)
Your Hawaiian Beach Get Away, Steps From Great Beach!
Kihei, HI
7% off
Price is AU$3,474
AU$3,474
for 7 nights, 1 apartment
AU$496 per night
includes taxes & fees
Image gallery for Just Reduced Value Season! 3rd Floor Unit Steps from the Beach

9.29.2 out of 10, Wonderful, (86 reviews)
Wonderful
(86 reviews)
Just Reduced Value Season! 3rd Floor Unit Steps from the Beach
Kihei, HI
7% off
Price is AU$3,151
AU$3,151
for 7 nights, 1 apartment
AU$450 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - The Skyline Trail
Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Sleeps 4 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
413 reviews(413 reviews)
Fisher's Hana Bay Hale, Across from Hana Bay
Sleeps 4 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
409 reviews(409 reviews)
Oceanview Condo in Hana-Let the ocean lull you to sleep
Sleeps 2 · 1 bedroom · 1 bathroom
9.29.2 out of 10
Wonderfulwonderful
115 reviews(115 reviews)
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
185 reviews(185 reviews)
Couples & Honeymooners. Privacy & Romance! 7 Sacred Pools
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
259 reviews(259 reviews)
Secluded cottage on Tropical flower farm
Sleeps 4 · 2 bedrooms
9.49.4 out of 10
Exceptionalexceptional
281 reviews(281 reviews)
Top rated rentals - The Skyline Trail
delightful quiet location
1010 out of 10
Exceptionalexceptional
110 reviews(110 reviews)
Lovely room and communal kitchen with views over the garden to the ocean.
It was a good base from which to explore Maui
Veronica W.
Stayed Aug 2024
Beautiful views and lovely property
1010 out of 10
Exceptionalexceptional
193 reviews(193 reviews)
This property is lovely and tucked away amongst green Hawaiian forest. Easy a quick access from Hana Hwy. Clean house with great facilities. Breakfast provided in the morning is a great touch. Would definitely stay again.
Tim B.
Stayed July 2023








