Hawaii Sailing Vacation Rentals

Planning a Hawaiian sailing vacation and need the perfect accommodation? These accommodations offer locations specific for amazing sailing experiences for all levels of expertise. Whether you’re a seasoned sailor or just want to try it for the first time, these locations will be perfect for you. Check out the wide selection of accommodations we have available spread throughout Hawaii in the prime sailing locations. Let CB Island Vacations help find your sailing vacation accommodations.

MAP

Located in Waikoloa

2 | 2 | 6

Located in Kailua-Kona

3 | 2 | 8

Located in Koloa

1 | 1 | 4

Located in Poipu

1 | 1 | 4

Located in Kihei

2 | 2 | 4

Located in Wailea

1 | 2 | 4

Located in Koloa

4 | 2.5 | 8

Located in Wailea

2 | 2 | 6

Located in Kailua Kona

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kailua-Kona

3 | 2.5 | 6

Located in Kaanapali

1 | 1 | 4

Located in Kihei

2 | 2 | 4

Located in Koloa

1 | 1 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in Wailea

1 | 1 | 2

Located in Wailea

1 | 2 | 4

Located in Koloa

3 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Waikoloa

2 | 2 | 6

Located in Kailua Kona

2 | 2 | 6

Located in Kailua-Kona

1 | 2 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in PRINCEVILLE

3 | 2 | 8

Located in Lahaina

1 | 1 | 4

Located in Wailea

1 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Wailea

2 | 2 | 4

Located in Kailua-Kona

1 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Wailea

2 | 2 | 4

Located in Wailea

1 | 2 | 2

Located in Kailua Kona

1 | 1 | 2

Located in Wailea

2 | 2 | 5

Located in Kihei

1 | 1 | 4

Located in Wailea

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Wailea

1 | 2 | 2

Located in Kailua-Kona

3 | 2.5 | 6

Located in Kahana

1 | 1 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in Koloa

3 | 3 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 7

Located in Kihei

1 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Wailea

3 | 3 | 8

Located in Kihei

1 | 1 | 4

Located in Kailua Kona

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Wailea

1 | 2 | 4

Located in Kihei

2 | 2 | 4

Located in Wailea

2 | 2 | 5

Located in Princeville

1 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Lihue

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Princeville

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Kailua Kona

2 | 2 | 4

Located in Kihei

1 | 1 | 4

Located in Kapalua

1 | 2 | 4

Located in Kailua-Kona

1 | 1 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in Kihei

2 | 2 | 4

Located in Kailua-Kona

2 | 2 | 6

Located in Waikoloa

2 | 2 | 6

Located in Wailea

3 | 3.5 | 8

Located in Kailua-Kona

3 | 3 | 8

Located in Kihei

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Kihei

1 | 2 | 4

Located in Kihei

1 | 1.5 | 4

Located in Kihei

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Wailuku

2 | 2 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in Wailea

2 | 2 | 7

Located in Kihei

1 | 1 | 4

Located in Wailea

3 | 3.5 | 8

Located in Wailea

1 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Koloa

5 | 4 | 12

Located in Wailea

1 | 2 | 5

Located in Kihei

1 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Poipu

2 | 3 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Kailua Kona

2 | 2 | 6

Located in Wailea

2 | 2.5 | 6

Located in Kaanapali

0 | 1 | 4

Located in Kihei

1 | 1 | 4

Located in Kailua Kona

1 | 2 | 4

Located in Kailua Kona

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Honolulu

0 | 1 | 4

Located in Wailea

2 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Wailea

3 | 2 | 6

Located in Kihei

3 | 2 | 6

Located in Kapaa

2 | 3 | 6

Located in Kahana

1 | 1 | 4

Located in Wailea

2 | 2 | 6

Located in Kapalua

2 | 2 | 4

Located in Wailea

1 | 2 | 4

Located in Wailea

1 | 2 | 4

Located in Kailua-Kona

1 | 1 | 4

Located in Wailea

3 | 3.5 | 8

Located in Kihei

2 | 2 | 6

Located in Wailea

1 | 2 | 2

Located in Kailua-Kona

1 | 1 | 2

Located in Kihei

2 | 2 | 4

Located in Poipu

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Kahana

1 | 1 | 4

Located in Wailea

2 | 2 | 6

Located in Waikoloa

3 | 3 | 6

Located in Wailea

2 | 2 | 4

Located in Kailua-Kona

3 | 2 | 6

Located in Kahana

1 | 1 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in Kapalua

2 | 3 | 4

Located in Poipu

2 | 2 | 6

Located in Koloa

4 | 3 | 10

Located in Kihei

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 7

Located in Kihei

2 | 2 | 6

Located in Kailua Kona

1 | 1 | 4

Located in Wailea

1 | 1 | 2

Located in Wailea

1 | 1 | 2

Located in Kihei

1 | 1 | 4

Located in Wailea

2 | 2 | 6

Located in Wailea

2 | 2 | 4

Located in Kihei

1 | 1 | 4

Located in Kaanapali

3 | 3 | 6

Located in Kihei

2 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Wailuku

1 | 1 | 2

Located in Kihei

1 | 2 | 4

Located in Waikoloa Village

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kaanapali

3 | 3 | 8

Located in Waikiki

0 | 1 | 2

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 7

Located in Wailea

2 | 2 | 6

Located in Kailua-Kona

3 | 2.5 | 6

Located in Koloa

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

1 | 2 | 4

Located in Kailua Kona

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Wailea

1 | 2 | 4

Located in Wailea

1 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Kailua Kona

2 | 2 | 6

Located in Wailea

2 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Honokowai

1 | 1 | 4

Located in Wailea

3 | 3.5 | 8

Located in Kailua-Kona

2 | 2 | 4

Located in Waikoloa

2 | 2.5 | 6

Located in Lahaina

2 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Kihei

4 | 4 | 16

Located in Wailea

2 | 2 | 6

Located in Kihei

2 | 2 | 5

Located in Wailea

1 | 2 | 4

Located in Wailea

1 | 2 | 4

Located in Kailua-Kona

1 | 1 | 2

Located in Waikoloa Village

2 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Wailuku

2 | 2 | 4

Located in Kihei

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Kailua-Kona

3 | 4 | 8

Located in Kailua-Kona

1 | 1 | 4

Located in Wailea

2 | 2 | 4

Located in Kihei

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Waikoloa

2 | 2.5 | 4

Located in Kihei

1 | 1 | 4

Located in Wailea

1 | 2 | 4

Located in Wailea

2 | 2.5 | 7

Located in Kihei

1 | 2 | 4

Located in Wailea

3 | 3.5 | 6

Located in Kihei

1 | 1 | 4

Located in Kihei

2 | 2 | 8

Located in Kihei

2 | 2 | 6

Located in Kailua Kona

3 | 2 | 6

Located in Kailua Kona

1 | 1 | 2

Located in Honokowai

1 | 1 | 4

Located in Lahaina

2 | 2 | 6

Located in Kailua Kona

2 | 2 | 6

Located in Kailua-Kona

2 | 2.5 | 4

Located in Wailea

2 | 2 | 6

Located in Waikoloa

3 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Wailea

3 | 3.5 | 6

Located in Koloa

2 | 1 | 4

Located in Wailea

2 | 2 | 4

Located in Lahaina

2 | 3 | 6

Located in Kihei

1 | 2 | 4

Located in Kihei

2 | 2 | 4

Located in Koloa

1 | 1 | 4

Located in Kihei

1 | 2 | 4

Located in KOLOA

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Kihei

1 | 1 | 2

Located in Waikoloa

2 | 2 | 5

Located in Kapalua

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

1 | 1 | 2

Located in Wailea

3 | 3.5 | 8

Located in Kihei

2 | 2 | 4

Located in Maalaea

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in Wailea

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Wailea

3 | 3.5 | 8

Located in Kihei

2 | 2 | 6

Located in Kihei

1 | 1 | 2

Located in Wailea

3 | 3.5 | 8

Located in Wailea

2 | 2 | 6

Located in Kailua Kona

2 | 2 | 4

Located in Kihei

1 | 1 | 4

Located in Wailea

2 | 2 | 4

Located in Kapaa

2 | 1 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in Princeville

3 | 3 | 6

Located in Kailua-Kona

3 | 3 | 6

Located in KAPAA

1 | 1 | 2

Located in Lahaina

1 | 2 | 4

Located in Koloa

3 | 2.5 | 9

Located in Kihei

3 | 3 | 6

Located in Wailea

2 | 2 | 6

Located in Wailea

2 | 2 | 5

Located in Kailua-Kona

3 | 2.5 | 6

Located in Kihei

1 | 1 | 2

Located in Kihei

2 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Wailea

3 | 3.5 | 8

Located in Kailua Kona

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Kihei

1 | 2 | 4

Located in Kihei

1 | 1 | 4

Located in Wailuku

1 | 1 | 4

Located in Kailua-Kona

1 | 1 | 4

Located in Kailua Kona

3 | 3 | 6

Located in KAPAA

1 | 1 | 4

Located in Waikoloa

1 | 1.5 | 4

Located in Waikoloa

1 | 1.5 | 4

Located in Kihei

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Wailea

1 | 2 | 4

Located in Wailea

3 | 3.5 | 8

Located in Wailea

2 | 2 | 4

Located in Kihei

4 | 3.5 | 14

Located in KOLOA

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Lihue

2 | 2 | 6

Located in Wailea

3 | 3 | 7

Located in Wailuku

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Waikoloa

2 | 2.5 | 6

Located in Princeville

2 | 2 | 6

Located in Kihei

1 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Koloa

1 | 1 | 2

Located in Koloa

1 | 1 | 4

Located in Kailua - Kona

2 | 2 | 4

Located in Honokowai

2 | 2 | 6

Located in Kahana

1 | 1 | 4

Located in Wailea

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Wailea

2 | 2 | 4

Located in Kailua-Kona

2 | 2 | 6

Located in Honolulu

0 | 1 | 3

Located in Wailea

2 | 2 | 6

Located in Wailea

2 | 2 | 6

Located in Kihei

2 | 2 | 4

Located in Kailua Kona

2 | 2 | 6

Located in Waikoloa

1 | 1 | 2

Located in Honokowai

1 | 1 | 4

Located in Kona

2 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in KIhei

2 | 2 | 4

Located in Anahola

2 | 2 | 6

Located in Kailua-Kona

1 | 1 | 4

Located in Kailua Kona

2 | 2 | 6

Located in Kahana

2 | 2 | 6

Located in Kihei

3 | 3 | 8

Located in Kihei

2 | 2 | 6

Located in Koloa

4 | 3.5 | 8

Located in Kihei

1 | 1 | 2

Located in Wailea

2 | 2 | 6

Located in Kona

4 | 4 | 10

Located in Kihei

2 | 2 | 4

Located in Kihei

2 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Wailea

1 | 2 | 4

Located in Kihei

1 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Kamuela

3 | 3 | 6

Located in Kailua Kona

1 | 1 | 4

Located in Kailua Kona

2 | 2 | 4

Located in Wailea

2 | 2 | 4

Located in Kailua Kona

1 | 2.5 | 8

Located in Wailea

2 | 2 | 7

Located in Kihei

2 | 2 | 4

Located in Kailua-Kona

2 | 2 | 4

Located in Kihei

2 | 1.5 | 4

Located in Kailua Kona

2 | 2 | 4

Located in Wailea

1 | 2 | 2

Located in Kihei

1 | 2 | 4

Located in Wailuku

1 | 1 | 4

Located in Lahaina

2 | 2.5 | 6

Located in Princeville

3 | 2 | 8

Located in Wailuku

2 | 2 | 6

Located in Poipu

2 | 2 | 6

Located in Kailua Kona

3 | 3.5 | 6

Located in Kihei

1 | 1 | 4

Located in Wailea

1 | 2 | 4

Located in Kahana

1 | 1 | 4

Located in Koloa

1 | 2 | 4

Located in Waikoloa

3 | 2 | 6

Located in Wailea

3 | 3.5 | 8

Located in Kailua-Kona

2 | 2 | 4

Located in Koloa

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 4

Located in Kailua Kona

2 | 2 | 6

Located in Kihei

1 | 1 | 2

Located in Napili

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Poipu

3 | 3 | 6

Located in Wailea

3 | 3.5 | 8

Located in Kihei

2 | 2 | 6

Located in Kailua-Kona

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

1 | 1 | 2

Located in Kihei

1 | 2 | 2

Located in Waikoloa

2 | 2 | 4

Located in Kaanapali

2 | 2 | 6

Located in Lahaina

1 | 1 | 2

Located in Kihei

1 | 1 | 4

Located in Lahaina

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 1 | 6

Located in Wailuku

1 | 1 | 4

Located in Kihei

2 | 2 | 6

Located in Kahana

3 | 2.5 | 8

Located in Kailua-Kona

2 | 2 | 4

Located in Wailea

1 | 2 | 3

Located in Waikoloa

3 | 3 | 6

Located in Kihei

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Wailea

1 | 2 | 4

Located in Wailea

1 | 2 | 4

Located in Kihei

2 | 2 | 4

Located in Wailea

2 | 2 | 6

Located in Kailua Kona

2 | 2 | 6

Located in Lihue

2 | 1.5 | 4

Located in Kihei

1 | 2 | 4

Located in Kailua Kona

2 | 2 | 4

Located in Wailea

2 | 2 | 4

Located in Kailua Kona

2 | 2 | 5

Located in Wailea

3 | 3.5 | 8

Located in Kihei

2 | 2 | 6

Located in Kihei

1 | 1 | 4

Located in KAPAA

2 | 1 | 4

Located in Kihei

1 | 2 | 5

Located in Kihei

1 | 1 | 4

Located in Kihei

1 | 1 | 4

Located in Kailua-Kona

1 | 1 | 2

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 6

Located in Kihei

2 | 2 | 8

Located in Kihei

2 | 2 | 6

Located in Kailua-Kona

1 | 1 | 4

Located in Kihei

1 | 2 | 4

Located in Kihei

2 | 2 | 6

Located in Kamuela

3 | 2 | 6

Located in Kailua-Kona

1 | 1 | 4

Located in Wailea

2 | 2 | 4

Located in Kahana

2 | 2.5 | 6

Located in Kihei

0 | 1 | 4

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