Hawaii Vacation Rentals near Hiking Trails

Explore our array of Hawaii vacation rentals near the best hiking spots in Maui, Oahu, Big Island, and Kauai. Whether you’re drawn to Maui’s scenic trails, Oahu’s iconic hikes like Diamond Head, Big Island’s diverse landscapes, or Kauai’s stunning Na Pali Coast trails, our rentals offer convenient access to these outdoor adventures. After a day of hiking, return to the comfort of our luxury rentals to unwind and recharge for your next exploration. Browse our Hawaii rentals now and plan a vacation that seamlessly blends the thrill of hiking with the comfort of a home away from home.

MAP

Located in Kailua Kona

3 | 3 | 6

Located in Wailuku

1 | 1 | 4

Located in Wailuku

1 | 1 | 2

Located in Wailea

3 | 3.5 | 8

Located in Kailua-Kona

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Kailua-Kona

3 | 2.5 | 6

Located in Kihei

4 | 3.5 | 14

Located in Kihei

1 | 1 | 4

Located in Poipu

3 | 3 | 6

Located in Kihei

2 | 2 | 6

Located in Wailea

1 | 2 | 2

Located in Kailua Kona

2 | 2 | 6

Located in Princeville

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Kihei

1 | 1 | 2

Located in Lahaina

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Kahana

1 | 1 | 4

Located in Wailea

2 | 2 | 6

Located in Wailea

2 | 2.5 | 6

Located in Kaanapali

3 | 3 | 6

Located in Wailea

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Waikoloa

2 | 2 | 4

Located in Lahaina

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Wailea

3 | 3.5 | 6

Located in Kihei

2 | 2 | 4

Located in Kihei

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Kihei

1 | 2 | 4

Located in Kailua-Kona

1 | 1 | 2

Located in Wailea

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 4

Located in Wailea

2 | 2 | 4

Located in Kapalua

2 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Lahaina

1 | 1 | 2

Located in Wailea

1 | 1 | 2

Located in Kihei

2 | 2 | 4

Located in Kailua Kona

2 | 2 | 6

Located in Wailea

3 | 3.5 | 8

Located in Wailea

2 | 2 | 7

Located in Wailuku

1 | 1 | 4

Located in Wailea

1 | 2 | 2

Located in KAPAA

2 | 1 | 4

Located in KOLOA

2 | 2 | 6

Located in Kailua-Kona

1 | 1 | 2

Located in Waikoloa

2 | 2 | 6

Located in Kapalua

2 | 3 | 4

Located in Kihei

2 | 2 | 6

Located in Wailuku

1 | 1 | 4

Located in Koloa

1 | 1 | 4

Located in Kihei

2 | 2 | 7

Located in Kailua Kona

1 | 1 | 4

Located in Kihei

1 | 2 | 5

Located in Kailua Kona

1 | 2 | 4

Located in Honolulu

0 | 1 | 3

Located in Waikoloa

1 | 1.5 | 4

Located in Kailua-Kona

2 | 2 | 6

Located in Koloa

2 | 1 | 4

Located in Wailea

3 | 3.5 | 8

Located in Wailea

3 | 2 | 6

Located in Kihei

1 | 1 | 2

Located in Kailua-Kona

1 | 1 | 4

Located in Wailea

1 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Kailua-Kona

1 | 1 | 2

Located in Kapaa

2 | 1 | 4

Located in Wailuku

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Lihue

2 | 1.5 | 4

Located in Kihei

2 | 2 | 6

Located in Kihei

1 | 2 | 2

Located in Kihei

2 | 2 | 4

Located in Kailua-Kona

3 | 2.5 | 6

Located in Kailua-Kona

2 | 2.5 | 4

Located in Wailea

2 | 2 | 6

Located in Kihei

1 | 2 | 4

Located in Koloa

1 | 2 | 4

Located in Wailea

3 | 3.5 | 8

Located in Kihei

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 4

Located in Kihei

2 | 2 | 7

Located in Wailea

2 | 2 | 6

Located in Koloa

1 | 1 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Wailea

1 | 2 | 4

Located in Wailea

2 | 2 | 4

Located in Kihei

2 | 2 | 4

Located in Kihei

1 | 1 | 2

Located in Wailea

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 4

Located in Koloa

4 | 3 | 10

Located in KOLOA

2 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Princeville

3 | 2 | 8

Located in Kailua Kona

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Honokowai

1 | 1 | 4

Located in Lahaina

2 | 2 | 6

Located in Wailea

2 | 2 | 4

Located in Poipu

2 | 2 | 6

Located in Kailua-Kona

3 | 2 | 8

Located in Kaanapali

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Kailua-Kona

3 | 4 | 8

Located in Wailea

3 | 3.5 | 8

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Waikoloa

3 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Wailuku

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Wailea

1 | 2 | 3

Located in Kailua Kona

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 6

Located in KIhei

2 | 2 | 4

Located in Waikoloa

1 | 1 | 2

Located in Kailua-Kona

2 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Kahana

1 | 1 | 4

Located in Kaanapali

0 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Waikoloa

1 | 1.5 | 4

Located in Princeville

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Kailua Kona

1 | 1 | 4

Located in Wailea

1 | 2 | 4

Located in Kihei

4 | 4 | 16

Located in Wailea

1 | 2 | 4

Located in Kihei

1 | 1 | 4

Located in Kailua Kona

2 | 2 | 4

Located in Anahola

2 | 2 | 6

Located in Wailuku

2 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Kailua Kona

2 | 2 | 4

Located in Kailua Kona

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Wailea

2 | 2 | 5

Located in Kihei

1 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Kailua-Kona

3 | 2.5 | 6

Located in Kihei

2 | 2 | 4

Located in Wailea

1 | 2 | 4

Located in Kihei

1 | 1 | 4

Located in Kailua-Kona

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Kihei

1 | 1 | 2

Located in Kihei

0 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kailua-Kona

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Kahana

1 | 1 | 4

Located in Kailua Kona

3 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Kapaa

2 | 3 | 6

Located in Lihue

2 | 2 | 6

Located in Kihei

1 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Wailea

2 | 2 | 4

Located in Wailea

3 | 3.5 | 8

Located in Kailua-Kona

1 | 1 | 4

Located in Wailea

3 | 3.5 | 8

Located in Kihei

2 | 2 | 8

Located in Waikoloa

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Wailea

3 | 3.5 | 8

Located in Lahaina

2 | 2.5 | 6

Located in Waikoloa

2 | 2.5 | 6

Located in Kailua-Kona

3 | 2 | 6

Located in Honokowai

1 | 1 | 4

Located in Lahaina

1 | 1 | 4

Located in Kahana

3 | 2.5 | 8

Located in Wailea

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Honokowai

1 | 1 | 4

Located in Kailua-Kona

1 | 2 | 4

Located in Wailea

1 | 2 | 4

Located in Kihei

3 | 2 | 6

Located in Kihei

1 | 2 | 4

Located in Kahana

2 | 2 | 6

Located in Wailea

2 | 2 | 4

Located in Kailua Kona

2 | 2 | 4

Located in Kailua-Kona

1 | 1 | 4

Located in Kamuela

3 | 2 | 6

Located in Wailea

3 | 3.5 | 6

Located in Wailea

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Princeville

3 | 3 | 6

Located in Wailea

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 5

Located in Kihei

3 | 3 | 8

Located in Wailea

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Lihue

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Honolulu

0 | 1 | 4

Located in Wailea

2 | 2 | 4

Located in Kihei

1 | 1.5 | 4

Located in Kapalua

1 | 2 | 4

Located in Wailea

2 | 2 | 4

Located in Kailua Kona

3 | 3.5 | 6

Located in Wailea

1 | 2 | 5

Located in Kailua-Kona

1 | 1 | 4

Located in Wailea

2 | 2 | 6

Located in Wailea

1 | 2 | 4

Located in Kailua Kona

2 | 2 | 6

Located in Wailea

2 | 2 | 7

Located in Wailea

1 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Waikoloa

3 | 3 | 6

Located in Kihei

2 | 1.5 | 4

Located in Wailea

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Wailea

1 | 2 | 4

Located in Koloa

4 | 3.5 | 8

Located in Koloa

3 | 3 | 6

Located in Kihei

1 | 1 | 4

Located in Kailua Kona

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 4

Located in Kihei

1 | 1 | 4

Located in Koloa

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Wailea

1 | 2 | 4

Located in Wailea

2 | 2.5 | 7

Located in Kahana

2 | 2.5 | 6

Located in Kihei

2 | 2 | 6

Located in Kailua Kona

1 | 2.5 | 8

Located in Wailea

1 | 1 | 2

Located in Waikoloa Village

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Wailea

1 | 2 | 4

Located in Kihei

2 | 2 | 4

Located in Kailua Kona

2 | 2 | 4

Located in Wailea

2 | 2 | 4

Located in Wailea

3 | 3.5 | 8

Located in Wailea

1 | 2 | 4

Located in Kaanapali

3 | 3 | 8

Located in Kahana

1 | 1 | 4

Located in Wailea

2 | 2 | 6

Located in Kamuela

3 | 3 | 6

Located in Kailua-Kona

2 | 2 | 4

Located in Kahana

1 | 1 | 4

Located in Kailua Kona

1 | 1 | 2

Located in Kihei

1 | 1 | 4

Located in Kihei

1 | 2 | 4

Located in Waikoloa

3 | 2 | 6

Located in Princeville

1 | 2 | 4

Located in Koloa

1 | 1 | 4

Located in Kihei

2 | 2 | 4

Located in PRINCEVILLE

3 | 2 | 8

Located in Kihei

1 | 2 | 4

Located in Wailea

3 | 3.5 | 8

Located in Poipu

2 | 3 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Wailea

2 | 2 | 5

Located in Kihei

1 | 1 | 4

Located in Kihei

2 | 2 | 8

Located in Wailea

3 | 3.5 | 8

Located in Kihei

2 | 2 | 6

Located in Waikiki

0 | 1 | 2

Located in Kailua-Kona

3 | 3 | 8

Located in Kailua Kona

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in Koloa

2 | 2 | 6

Located in Lahaina

1 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Poipu

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Wailuku

2 | 2 | 4

Located in Kapalua

2 | 2 | 6

Located in Kihei

1 | 2 | 4

Located in Kihei

1 | 1 | 4

Located in Kaanapali

1 | 1 | 4

Located in Kihei

2 | 2 | 4

Located in Wailea

2 | 2 | 5

Located in KAPAA

1 | 1 | 4

Located in Kailua Kona

2 | 2 | 4

Located in Koloa

3 | 2 | 6

Located in Waikoloa

2 | 2 | 6

Located in KAPAA

1 | 1 | 2

Located in Kihei

1 | 2 | 4

Located in Kihei

1 | 1 | 2

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kailua Kona

2 | 2 | 6

Located in Lahaina

2 | 3 | 6

Located in Wailea

1 | 2 | 4

Located in Kihei

1 | 1 | 4

Located in Wailea

1 | 2 | 4

Located in Wailea

2 | 2 | 4

Located in Kailua-Kona

1 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Wailea

1 | 2 | 4

Located in Kihei

1 | 1 | 4

Located in Wailea

1 | 2 | 2

Located in Kahana

1 | 1 | 4

Located in Wailea

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Kailua-Kona

3 | 2.5 | 6

Located in Wailea

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Koloa

1 | 1 | 2

Located in Kihei

1 | 1 | 4

Located in Kihei

1 | 2 | 4

Located in Wailea

2 | 2 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in Maalaea

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Kailua - Kona

2 | 2 | 4

Located in Wailea

2 | 2 | 4

Located in Kailua Kona

1 | 1 | 4

Located in Kihei

1 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Wailea

2 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in Napili

1 | 1 | 4

Located in Kailua Kona

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Poipu

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Wailea

1 | 1 | 2

Located in Koloa

5 | 4 | 12

Located in Waikoloa Village

2 | 2 | 4

Located in Kailua Kona

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Wailea

3 | 3 | 7

Located in Kihei

2 | 1 | 6

Located in Wailea

2 | 2 | 6

Located in Honokowai

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Wailea

2 | 2 | 4

Located in Kailua-Kona

3 | 3 | 6

Located in Wailea

3 | 3.5 | 8

Located in Kona

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Koloa

3 | 2.5 | 9

Located in Koloa

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Wailea

2 | 2 | 4

Located in Waikoloa

2 | 2.5 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Kailua Kona

1 | 1 | 2

Located in Kihei

2 | 2 | 7

Located in Kona

4 | 4 | 10

Located in Wailea

2 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 4

Located in Waikoloa

3 | 3 | 6

Located in Poipu

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Waikoloa

2 | 2.5 | 4

Located in Wailea

2 | 2 | 6

Located in Wailea

1 | 2 | 4

Located in Wailea

3 | 3 | 8

Located in Koloa

4 | 2.5 | 8

Located in Waikoloa

2 | 2 | 5

Located in Kihei

1 | 2 | 4

Located in Kihei

3 | 3 | 6

Located in Kailua Kona

2 | 2 | 6

Located in Kihei

1 | 1 | 2

Located in Kihei

2 | 2 | 6

Located in Wailea

1 | 2 | 2

Located in Kihei

2 | 2 | 6

Located in Wailea

2 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Wailea

1 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Kailua Kona

2 | 2 | 5

Located in Kihei

1 | 1 | 2

Located in Kihei

1 | 1 | 4

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