Holiday rentals near The Skyline Trail
We found 3,272 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:22 Aug - 29 Aug
Image gallery for Kula Luxury Retreat With Stunning Ocean & Mountain Views!
1010 out of 10 rating
Exceptional
(72 reviews)
Kula Luxury Retreat With Stunning Ocean & Mountain Views!
Kihei, HI
8% off
Price is AU$16,640
AU$16,640
AU$2,377 per night
includes taxes & fees
Image gallery for Beautiful beaches for swimming and sunsets! Kamaole Sands 3-207
9.69.6 out of 10 rating
Exceptional
(19 reviews)
Beautiful beaches for swimming and sunsets! Kamaole Sands 3-207
Kihei, HI
6% off
Price is AU$2,605
AU$2,605
AU$372 per night
includes taxes & fees
Image gallery for "ALOHA" Ocean View Maui Kamaole Condo in South Maui
1010 out of 10 rating
Exceptional
(78 reviews)
"ALOHA" Ocean View Maui Kamaole Condo in South Maui
Kihei, HI
11% off
Price is AU$3,998
AU$3,998
AU$571 per night
includes taxes & fees
Image gallery for Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Wailea Beach Villas M311 Seaview Sanctuary Luxury Oceanview Condo
Kihei, HI
8% off
Price is AU$16,386
AU$16,386
AU$2,341 per night
includes taxes & fees
Image gallery for Just another day in Paradise!
9.89.8 out of 10 rating
Exceptional
(111 reviews)
Just another day in Paradise!
Kihei, HI
7% off
Price is AU$6,121
AU$6,121
AU$874 per night
includes taxes & fees
Image gallery for South Kihei Ocean View & easy walk to the beach.
1010 out of 10 rating
Exceptional
(85 reviews)
South Kihei Ocean View & easy walk to the beach.
Kihei, HI
7% off
Price is AU$3,160
AU$3,160
AU$451 per night
includes taxes & fees
Image gallery for Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms
9.49.4 out of 10 rating
Exceptional
(39 reviews)
Wailea Beach Villas Luxury Four Bedroom Condo L109 Ginger And Palms
Kihei, HI
8% off
Price is AU$16,981
AU$16,981
AU$2,426 per night
includes taxes & fees
Image gallery for Wailea Ekahi 54C: Best View & New Kitchen
1010 out of 10 rating
Exceptional
(36 reviews)
Wailea Ekahi 54C: Best View & New Kitchen
Kihei, HI
7% off
Price is AU$7,502
AU$7,502
AU$1,072 per night
includes taxes & fees
Image gallery for Spectacular ocean and beach view 2 BR condo, steps from the ocean!
1010 out of 10 rating
Exceptional
(92 reviews)
Spectacular ocean and beach view 2 BR condo, steps from the ocean!
Kihei, HI
7% off
Price is AU$4,460
AU$4,460
AU$637 per night
includes taxes & fees
Image gallery for CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal
9.89.8 out of 10 rating
Exceptional
(75 reviews)
CLOUD 9 BEACH HOUSE, Walk to Beach, Oceanview. Many Amenities, Very Clean, Legal
Kihei, HI
7% off
Price is AU$9,361
AU$9,361
AU$1,337 per night
includes taxes & fees
Image gallery for DIRECT BEACHFRONT WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS 4Bd 3BA 3892 s.f.
1010 out of 10 rating
Exceptional
(111 reviews)
DIRECT BEACHFRONT WAILEA PANORAMIC OCEAN & OUTER ISLAND VIEWS 4Bd 3BA 3892 s.f.
Kihei, HI
8% off
Price is AU$26,165
AU$26,165
AU$3,738 per night
includes taxes & fees
Image gallery for Nice Large Floor Plan / Pool View Unit B-201
1010 out of 10 rating
Exceptional
(153 reviews)
Nice Large Floor Plan / Pool View Unit B-201
Kihei, HI
7% off
Price is AU$3,874
AU$3,874
AU$553 per night
includes taxes & fees
Image gallery for Oceanside -Walk to Beach- Modern & Serene- 2BD, 2BA- Kihei Alii Kai-Full Remodel
1010 out of 10 rating
Exceptional
(23 reviews)
Oceanside -Walk to Beach- Modern & Serene- 2BD, 2BA- Kihei Alii Kai-Full Remodel
Kihei, HI
7% off
Price is AU$5,690
AU$5,690
AU$813 per night
includes taxes & fees
Image gallery for Hula On In to Beach House Chic Style, Click the Video tour below!
1010 out of 10 rating
Exceptional
(130 reviews)
Hula On In to Beach House Chic Style, Click the Video tour below!
Kihei, HI
7% off
Price is AU$5,113
AU$5,113
AU$730 per night
includes taxes & fees
Image gallery for BEACH LUX VILLA with AWESOME VIEW! CLICK on “About this Property” for a TOUR!
1010 out of 10 rating
Exceptional
(126 reviews)
BEACH LUX VILLA with AWESOME VIEW! CLICK on “About this Property” for a TOUR!
Kihei, HI
7% off
Price is AU$4,098
AU$4,098
AU$585 per night
includes taxes & fees
Image gallery for Fully remodeled & equipped condo, steps to amazing beaches!
9.49.4 out of 10 rating
Exceptional
(158 reviews)
Fully remodeled & equipped condo, steps to amazing beaches!
Kihei, HI
7% off
Price is AU$3,709
AU$3,709
AU$530 per night
includes taxes & fees
Image gallery for BEST VALUE! Partial Ocean View-Prime location-Steps to Kam II Beach-Redecorated
9.49.4 out of 10 rating
Exceptional
(124 reviews)
BEST VALUE! Partial Ocean View-Prime location-Steps to Kam II Beach-Redecorated
Kihei, HI
7% off
Price is AU$2,838
AU$2,838
AU$405 per night
includes taxes & fees
Image gallery for Gated 2-story beach house with big yard
1010 out of 10 rating
Exceptional
(55 reviews)
Gated 2-story beach house with big yard
Kihei, HI
7% off
Price is AU$7,637
AU$7,637
AU$1,091 per night
includes taxes & fees
Image gallery for Beautiful OCEAN View! Across from the BEACH! From 140 a night!
9.09.0 out of 10 rating
Wonderful
(136 reviews)
Beautiful OCEAN View! Across from the BEACH! From 140 a night!
Kihei, HI
7% off
Price is AU$2,257
AU$2,257
AU$322 per night
includes taxes & fees
Image gallery for Wailea Ekahi 51F Oceanview - Walk to Beach
9.89.8 out of 10 rating
Exceptional
(97 reviews)
Wailea Ekahi 51F Oceanview - Walk to Beach
Kihei, HI
8% off
Price is AU$3,664
AU$3,664
AU$523 per night
includes taxes & fees
Image gallery for Ocean view! 3 Bedrooms! Great Location!
9.69.6 out of 10 rating
Exceptional
(121 reviews)
Ocean view! 3 Bedrooms! Great Location!
Kihei, HI
8% off
Price is AU$6,395
AU$6,395
AU$914 per night
includes taxes & fees
Image gallery for NEWLY REMODELED! Beautiful & Spacious- Two Story Wailea Ocean View 2BR/2.5BA
1010 out of 10 rating
Exceptional
(102 reviews)
NEWLY REMODELED! Beautiful & Spacious- Two Story Wailea Ocean View 2BR/2.5BA
Kihei, HI
7% off
Price is AU$7,162
AU$7,162
AU$1,023 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 rating
Exceptional
(86 reviews)
Maui 🌺 Private Home in Wailea Kihei with 3 bed 2 bath Best Beaches on Maui
Kihei, HI
7% off
Price is AU$8,269
AU$8,269
AU$1,181 per night
includes taxes & fees
Image gallery for 3 minute walk to beach in South Maui!
9.89.8 out of 10 rating
Exceptional
(113 reviews)
3 minute walk to beach in South Maui!
Kihei, HI
7% off
Price is AU$4,672
AU$4,672
AU$667 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - The Skyline Trail
Showing deals for: 20 Aug - 23 Aug
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
177 reviews(177 reviews)
The current price is AU$2,293
AU$2,293
for 3 nights, 1 home
AU$764 per night
includes taxes & fees
Beautiful Cottage in the heart of Hana, sleeps 2 with 1bed/1bath
Sleeps 2 · 1 bedroom · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
183 reviews(183 reviews)
The current price is AU$2,106
AU$2,106
for 3 nights, 1 cottage
AU$702 per night
includes taxes & fees
Breathtaking Oceanfront Location, Gorgeous Views, Stroll to Hamoa Beach, Hot Tub
Sleeps 6 · 3 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
167 reviews(167 reviews)
The current price is AU$6,433
AU$6,433
for 3 nights, 1 home
AU$2,144 per night
includes taxes & fees
360 Degree Ocean And Mountain Views From This Stunning Home.
Sleeps 4 · 2 bedrooms · 2 bathrooms
9.89.8 out of 10
Exceptionalexceptional
139 reviews(139 reviews)
The current price is AU$2,009
AU$2,009
for 3 nights, 1 home
AU$670 per night
includes taxes & fees
Great location between Hana Town and Hamoa Beach, private, family-friendly
Sleeps 4 · 2 bedrooms · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
226 reviews(226 reviews)
The current price is AU$2,039
AU$2,039
for 3 nights, 1 cottage
AU$680 per night
includes taxes & fees
Amazing Hana Bay Beach Cottage Location! 5-Minute Walk to Hana town & beaches!
Sleeps 4 · 2 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
16 reviews(16 reviews)
The current price is AU$5,977
AU$5,977
for 3 nights, 1 home
AU$1,992 per night
includes taxes & fees
Top rated rentals - The Skyline Trail
Incredible Stay
1010 out of 10
Exceptionalexceptional
72 reviews(72 reviews)
Outstanding property in an perfect location
1010 out of 10
Exceptionalexceptional
190 reviews(190 reviews)
Kihei
1010 out of 10
Exceptionalexceptional
199 reviews(199 reviews)
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