Holiday rentals near The Skyline Trail
We found 3,203 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:3 Oct - 10 Oct
Image gallery for Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01
9.89.8 out of 10 rating
Exceptional
(185 reviews)
Beautiful Hana, Near Waianapanapa State Park. STR 216/0003 TA186-656-9728-01
Hana, HI
12% off
Price is AU$4,279
AU$4,279
AU$611 per night
includes taxes & fees
Image gallery for Luxury Upcountry Villa with breathtaking views
1010 out of 10 rating
Exceptional
(41 reviews)
Luxury Upcountry Villa with breathtaking views
Makawao, HI
8% off
Price is AU$9,778
AU$9,778
AU$1,397 per night
includes taxes & fees
Image gallery for Hana Harvest Cottage
9.49.4 out of 10 rating
Exceptional
(64 reviews)
Hana Harvest Cottage
Hana, HI
7% off
Price is AU$5,580
AU$5,580
AU$797 per night
includes taxes & fees
Image gallery for Great location between Hana Town and Hamoa Beach, private, family-friendly
9.89.8 out of 10 rating
Exceptional
(229 reviews)
Great location between Hana Town and Hamoa Beach, private, family-friendly
Hana, HI
8% off
Price is AU$4,081
AU$4,081
AU$583 per night
includes taxes & fees
Image gallery for Oceanfront #3 at Hana Kai Maui - 1 Bedroom Corner Unit 100ʻ from Water!
9.49.4 out of 10 rating
Exceptional
(19 reviews)
Oceanfront #3 at Hana Kai Maui - 1 Bedroom Corner Unit 100ʻ from Water!
Hana, HI
8% off
Price is AU$5,470
AU$5,470
AU$781 per night
includes taxes & fees
Image gallery for Mountain to Ocean Views Pole House @ Maui Adventure Villa
1010 out of 10 rating
Exceptional
(223 reviews)
Mountain to Ocean Views Pole House @ Maui Adventure Villa
Haiku, HI
8% off
Price is AU$4,456
AU$4,456
AU$637 per night
includes taxes & fees
Image gallery for Oceanview #202 at Hana Kai Maui - Lofted Studio Upper Floor, Panoramic View!
9.69.6 out of 10 rating
Exceptional
(61 reviews)
Oceanview #202 at Hana Kai Maui - Lofted Studio Upper Floor, Panoramic View!
Hana, HI
7% off
Price is AU$4,920
AU$4,920
AU$703 per night
includes taxes & fees
Image gallery for Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
9.29.2 out of 10 rating
Wonderful
(142 reviews)
Beautiful home in the Heart of Hana, sleeps 4 with 2br/1b
Hana, HI
7% off
Price is AU$4,632
AU$4,632
AU$662 per night
includes taxes & fees
Image gallery for Partial Oceanview #106 at Hana Kai Maui - Studio unit with a really nice view!
8.88.8 out of 10 rating
Excellent
(35 reviews)
Partial Oceanview #106 at Hana Kai Maui - Studio unit with a really nice view!
Hana, HI
7% off
Price is AU$4,370
AU$4,370
AU$624 per night
includes taxes & fees
Image gallery for Hana Bay View 3 BR/2 BA house sleeps 6 comfortably with 2 patios.
9.49.4 out of 10 rating
Exceptional
(28 reviews)
Hana Bay View 3 BR/2 BA house sleeps 6 comfortably with 2 patios.
Hana, HI
7% off
Price is AU$7,309
AU$7,309
AU$1,044 per night
includes taxes & fees
Image gallery for Reduced rates. Eco friendly elegant modern home, gorgeous Ocean & Mt views
1010 out of 10 rating
Exceptional
(171 reviews)
Reduced rates. Eco friendly elegant modern home, gorgeous Ocean & Mt views
Kula, HI
7% off
Price is AU$8,376
AU$8,376
AU$1,197 per night
includes taxes & fees
Image gallery for HAWAIIAN DREAM TEMPLE - w/Private Hot Tub and Shared Pool - Permit#BBPH2012-0004
9.89.8 out of 10 rating
Exceptional
(84 reviews)
HAWAIIAN DREAM TEMPLE - w/Private Hot Tub and Shared Pool - Permit#BBPH2012-0004
Haiku, HI
14% off
Price is AU$4,871
AU$4,871
AU$696 per night
includes taxes & fees
Image gallery for PICTURESQUE OCEAN VIEW CONDO - LAST MINUTE DEAL! BEAUTIFUL WAILEA AT ELUA 2002
1010 out of 10 rating
Exceptional
(92 reviews)
PICTURESQUE OCEAN VIEW CONDO - LAST MINUTE DEAL! BEAUTIFUL WAILEA AT ELUA 2002
Kihei, HI
7% off
Price is AU$10,526
AU$10,526
AU$1,504 per night
includes taxes & fees
Image gallery for Best Location! Beachy 3 BR Home, 4 miles to Ho'okipa, Permit #STPH2015/0006
1010 out of 10 rating
Exceptional
(31 reviews)
Best Location! Beachy 3 BR Home, 4 miles to Ho'okipa, Permit #STPH2015/0006
Haiku, HI
14% off
Price is AU$4,054
AU$4,054
AU$579 per night
includes taxes & fees
Image gallery for Great Location, Clean, Beachy 1BR Cottage
9.89.8 out of 10 rating
Exceptional
(63 reviews)
Great Location, Clean, Beachy 1BR Cottage
Haiku, HI
7% off
Price is AU$3,051
AU$3,051
AU$436 per night
includes taxes & fees
Image gallery for Plumeria Room on a Lush Farm on Maui's North Shore
1010 out of 10 rating
Exceptional
(7 reviews)
Plumeria Room on a Lush Farm on Maui's North Shore
Haiku, HI
8% off
Price is AU$5,287
AU$5,287
AU$755 per night
includes taxes & fees
Image gallery for Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.
9.09.0 out of 10 rating
Wonderful
(23 reviews)
Charming bed & breakfast on the slopes of Haleakala with AC, WiFi.
Makawao, HI
7% off
Price is AU$2,526
AU$2,526
AU$361 per night
includes taxes & fees
Image gallery for Peaceful & Private Studio - 12 Acre Hobby Organic Fruit Farm - Beach 10 minutes
9.89.8 out of 10 rating
Exceptional
(86 reviews)
Peaceful & Private Studio - 12 Acre Hobby Organic Fruit Farm - Beach 10 minutes
Haiku, HI
7% off
Price is AU$3,353
AU$3,353
AU$479 per night
includes taxes & fees
Image gallery for Oceanfront #1 at Hana Kai Maui - 1 Bedroom, Corner Unit 100ʻ from Water!
9.89.8 out of 10 rating
Exceptional
(40 reviews)
Oceanfront #1 at Hana Kai Maui - 1 Bedroom, Corner Unit 100ʻ from Water!
Hana, HI
8% off
Price is AU$5,530
AU$5,530
AU$790 per night
includes taxes & fees
Image gallery for New! Palms 702 - Romantic Retreat - Split AC in Bedroom - Open-Air Living Area
9.29.2 out of 10 rating
Wonderful
(13 reviews)
New! Palms 702 - Romantic Retreat - Split AC in Bedroom - Open-Air Living Area
Kihei, HI
6% off
Price is AU$3,230
AU$3,230
AU$461 per night
includes taxes & fees
Image gallery for Makena Surf C-107: Premier Luxury Condo • Largest 2-Bed • Oceanviews • Local Art
1010 out of 10 rating
Exceptional
(89 reviews)
Makena Surf C-107: Premier Luxury Condo • Largest 2-Bed • Oceanviews • Local Art
Kihei, HI
6% off
Price is AU$12,993
AU$12,993
AU$1,856 per night
includes taxes & fees
Image gallery for North Shore Guest House @ Maui Adventure Villa
9.69.6 out of 10 rating
Exceptional
(94 reviews)
North Shore Guest House @ Maui Adventure Villa
Haiku, HI
8% off
Price is AU$6,046
AU$6,046
AU$864 per night
includes taxes & fees
Image gallery for Amazing Hana Bay Beach Cottage Location! 5-Minute Walk to Hana town & beaches!
1010 out of 10 rating
Exceptional
(16 reviews)
Amazing Hana Bay Beach Cottage Location! 5-Minute Walk to Hana town & beaches!
Hana, HI
15% off
Price is AU$7,466
AU$7,466
AU$1,067 per night
includes taxes & fees
Image gallery for Ekahi 27A: Priceless Ocean View from a Private Lanai
9.89.8 out of 10 rating
Exceptional
(35 reviews)
Ekahi 27A: Priceless Ocean View from a Private Lanai
Kihei, HI
7% off
Price is AU$6,295
AU$6,295
AU$899 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: 30 Sept - 3 Oct
IDEAL BEACH LOCATION 2 BR LARGE DECK "PRIVATE'
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
178 reviews(178 reviews)
The current price is AU$2,241
AU$2,241
for 3 nights, 1 home
AU$747 per night
includes taxes & fees
Secluded cottage on Tropical flower farm
Sleeps 4 · 2 bedrooms
9.69.6 out of 10
Exceptionalexceptional
259 reviews(259 reviews)
The current price is AU$1,972
AU$1,972
for 3 nights, 1 cottage
AU$657 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
229 reviews(229 reviews)
The current price is AU$2,078
AU$2,078
for 3 nights, 1 cottage
AU$693 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$3,711
AU$3,711
for 3 nights, 1 home
AU$1,237 per night
includes taxes & fees
MINUTES TO HAMOA BEACH, BEST LOCATION IN HANA
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
239 reviews(239 reviews)
The current price is AU$2,241
AU$2,241
for 3 nights, 1 cottage
AU$747 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$5,716
AU$5,716
for 3 nights, 1 home
AU$1,905 per night
includes taxes & fees
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