Columbus Day Timeshare Rentals in Hawaii

Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,384 ($626/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,584 ($798/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,584 ($798/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Oct 11–18, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,129 ($876/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Oct 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Oct 11–18, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,568 ($510/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$6,129 ($876/night)

Verified & Protected

Wyndham Kauai Coast Resort at the Beachboy

Kapaa, Hawaii

Oct 9–19, 2026 (10 nights)
1 bed/1 bath, sleeps 4
$3,949 ($395/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,167 ($595/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Oct 7–14, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,385 ($626/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Oct 10–17, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,750 ($393/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Oct 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,402 ($914/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,015 ($859/night)

Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Oct 9–16, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,748 ($821/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,385 ($626/night)

Verified & Protected

Maui Schooner

Kihei, Hawaii

Oct 9–16, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,824 ($260/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,948 ($564/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Oct 11–18, 2026 (7 nights)
Studio/1 bath, sleeps 2
$3,077 ($440/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Oct 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,603 ($658/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Oct 10–17, 2026 (7 nights)
Studio/1 bath, sleeps 2
$2,423 ($346/night)

Verified & Protected

Lawai Beach Resort

Koloa, Hawaii

Oct 8–15, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,314 ($331/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,622 ($517/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Oct 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,107 ($872/night)

Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Oct 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,603 ($658/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$9,677 ($1,382/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,641 ($377/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,213 ($459/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,505 ($358/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,679 ($668/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,750 ($393/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$6,565 ($938/night)

Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,294 ($471/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Oct 11–18, 2026 (7 nights)
Studio/1 bath, sleeps 2
$3,077 ($440/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Oct 10–17, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,603 ($658/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Oct 11–18, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$7,982 ($1,140/night)

Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,494 ($642/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,467 ($352/night)

Verified & Protected

The Cliffs at Princeville

Princeville, Hawaii

Oct 11–18, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$2,423 ($346/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Oct 10–17, 2026 (7 nights)
Studio/1 bath, sleeps 2
$2,314 ($331/night)

Verified & Protected

Paniolo Greens

Waikoloa Village, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,550 ($221/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,072 ($439/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Oct 9–16, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,854 ($408/night)

Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Oct 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,385 ($626/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Oct 10–17, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,077 ($440/night)

Verified & Protected

Club Wyndham Royal Sea Cliff

Kailua-Kona, Hawaii

Oct 7–14, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,314 ($331/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Oct 7–13, 2026 (6 nights)
Studio/1 bath, sleeps 2
$2,205 ($368/night)

Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,167 ($595/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,693 ($813/night)