Holiday rentals near The Skyline Trail
We found 3,341 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:20 Mar - 27 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
7% off
Price is AU$3,739
AU$3,739
for 7 nights, 1 apartment
AU$534 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.
Wailea-Makena
7% off
Price is AU$5,263
AU$5,263
for 7 nights, 1 apartment
AU$752 per night
includes taxes & fees
Image gallery for Hana Harvest Cottage
9.49.4 out of 10, Exceptional, (65 reviews)
Exceptional
(65 reviews)
Hana Harvest Cottage
Hana
8% off
Price is AU$5,531
AU$5,531
for 7 nights, 1 cottage
AU$790 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
7% off
Price is AU$6,875
AU$6,875
for 7 nights, 1 apartment
AU$982 per night
includes taxes & fees
Image gallery for Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
9.69.6 out of 10, Exceptional, (191 reviews)
Exceptional
(191 reviews)
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Hana
7% off
Price is AU$3,854
AU$3,854
for 7 nights, 1 cottage
AU$551 per night
includes taxes & fees
Image gallery for Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
1010 out of 10, Exceptional, (89 reviews)
Exceptional
(89 reviews)
Ocean View Cabin located on Organic Coffee Farm with Hiking Trails
Makawao
7% off
Price is AU$4,556
AU$4,556
for 7 nights, 1 cottage
AU$651 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
7% off
Price is AU$10,531
AU$10,531
for 7 nights, 1 home
AU$1,504 per night
includes taxes & fees
Image gallery for Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.
9.49.4 out of 10, Exceptional, (90 reviews)
Exceptional
(90 reviews)
Upcountry Short Term Rental Home with Ocean and Mt Views, Close to Makawao Town.
Makawao
8% off
Price is AU$7,361
AU$7,361
for 7 nights, 1 home
AU$1,052 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
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 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
7% off
Price is AU$4,939
AU$4,939
for 7 nights, 1 apartment
AU$706 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, (158 reviews)
Exceptional
(158 reviews)
Maui Banyan fave! Ocean View, Renovated, Steps to the Beach, King Bed, Split AC
Kihei
7% off
Price is AU$4,080
AU$4,080
for 7 nights, 1 apartment
AU$583 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
9% off
Price is AU$4,034
AU$4,034
for 7 nights, 1 apartment
AU$576 per night
includes taxes & fees
Image gallery for Largest ‘One of a Kind’ 2-bd 2-Bth Condo 🏄 New Air Conditioner throughout🌴
9.69.6 out of 10, Exceptional, (91 reviews)
Exceptional
(91 reviews)
Largest ‘One of a Kind’ 2-bd 2-Bth Condo 🏄 New Air Conditioner throughout🌴
Kihei, Maui
7% off
Price is AU$4,153
AU$4,153
for 7 nights, 1 apartment
AU$593 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
Wailea-Makena
7% off
Price is AU$4,398
AU$4,398
for 7 nights, 1 apartment
AU$628 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
9% off
Price is AU$3,295
AU$3,295
for 7 nights, 1 apartment
AU$471 per night
includes taxes & fees
Image gallery for The Best of 'The Palms' - Panoramic Views, Private End Unit #1102
9.89.8 out of 10, Exceptional, (45 reviews)
Exceptional
(45 reviews)
The Best of 'The Palms' - Panoramic Views, Private End Unit #1102
Wailea-Makena
7% off
Price is AU$7,269
AU$7,269
for 7 nights, 1 apartment
AU$1,038 per night
includes taxes & fees
Image gallery for 3 minute walk to beach in South Maui!
9.89.8 out of 10, Exceptional, (117 reviews)
Exceptional
(117 reviews)
3 minute walk to beach in South Maui!
Kihei
7% off
Price is AU$4,555
AU$4,555
for 7 nights, 1 apartment
AU$651 per night
includes taxes & fees
Image gallery for FULL OCEAN VIEW, 2nd Floor 2 BR/1 BA, BEST STAND-UP PADDLEBOARDING ON MAUI!
1010 out of 10, Exceptional, (131 reviews)
Exceptional
(131 reviews)
FULL OCEAN VIEW, 2nd Floor 2 BR/1 BA, BEST STAND-UP PADDLEBOARDING ON MAUI!
Kihei
7% off
Price is AU$3,910
AU$3,910
for 7 nights, 1 apartment
AU$559 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
7% off
Price is AU$4,350
AU$4,350
for 7 nights, 1 apartment
AU$621 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!
Wailea-Makena
7% off
Price is AU$8,092
AU$8,092
for 7 nights, 1 apartment
AU$1,156 per night
includes taxes & fees
Image gallery for Fantastic home away from home on Island!! Recently remodeled and new furnishings
9.09.0 out of 10, Wonderful, (14 reviews)
Wonderful
(14 reviews)
Fantastic home away from home on Island!! Recently remodeled and new furnishings
Kihei
11% off
Price is AU$3,319
AU$3,319
for 7 nights, 1 apartment
AU$474 per night
includes taxes & fees
Image gallery for Maui Kamaole I-205; 2 bedroom ocean view condo
9.69.6 out of 10, Exceptional, (76 reviews)
Exceptional
(76 reviews)
Maui Kamaole I-205; 2 bedroom ocean view condo
Kihei
7% off
Price is AU$5,357
AU$5,357
for 7 nights, 1 apartment
AU$765 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
9% off
Price is AU$3,355
AU$3,355
for 7 nights, 1 apartment
AU$479 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, (221 reviews)
Exceptional
(221 reviews)
Temp.Aug. sp Pro Design Ground fl. Lovey flower gardens Sleeps 6 .
Kihei
7% off
Price is AU$5,243
AU$5,243
for 7 nights, 1 apartment
AU$749 per night
includes taxes & fees
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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
414 reviews(414 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
Great retreat
1010 out of 10
Exceptionalexceptional
197 reviews(197 reviews)
Simple, clean and homely. A quiet base for exploring the island
Bo D.
Stayed July 2024
Fantastic farm stay
1010 out of 10
Exceptionalexceptional
136 reviews(136 reviews)
Amazing charming farmhouse about 10 minutes drive from Hana. Very clean and nicely furnished. Had everything you could need. Fresh farm eggs was a nice touch! Cute farm animals and very welcoming host.
Evie Y.
Stayed June 2024
Great value for money
1010 out of 10
Exceptionalexceptional
123 reviews(123 reviews)
Good location near the beach. Was perfect for what we needed. Would stay here again in future.
Nicholas V.
Stayed June 2023
Wonderful stay in Maui
1010 out of 10
Exceptionalexceptional
86 reviews(86 reviews)
Fantastic property in a great location! Communicative, friendly hosts and clean, perfectly suited apartment in quiet, relaxing Grand Champions.
Alison T.
Stayed Apr 2023
Kihei
1010 out of 10
Exceptionalexceptional
210 reviews(210 reviews)
We loved our stay, everything was exactly as described. Thanks for everything!
Clark T.
Stayed Sept 2019
Amazing Condo
1010 out of 10
Exceptionalexceptional
201 reviews(201 reviews)
This condo was truly the best one we stayed at during our Hawaiian visit (we stayed in 7 different places). Immaculate and everything you could think of was supplied. Having the washer/dryer was an absolute bonus. Well situated so even though we had a car, we could walk to shops and restaurants. The owners have done a fab job with the renovations and everything is very tastefully decorated. I would highly recommend this home away from home!
KYM C.
Stayed July 2018
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value