Columbus Day Timeshare Rentals
Observed on the second Monday in October, Columbus Day is a U.S. federal holiday that creates a long weekend for many travelers. While some states now recognize the day as Indigenous Peoples’ Day, the extended weekend is still a great time to enjoy a fall getaway and take advantage of the changing seasons.
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 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
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
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
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
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
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
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
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
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
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
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
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 9–16, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)