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
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 11–18, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,725 ($345/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($397/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,268 ($423/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,462 ($487/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
Verified & Protected
Kamaole Beach Club
Kihei, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 6–16, 2026 (10 nights)
- 2 bed/2 bath, sleeps 6
- $4,472 ($447/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,968 ($424/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Club Wyndham Ka 'Eo Kai
Princeville, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,531 ($362/night)
Verified & Protected
Kohala Suites by Hilton Grand Vacations
Waikoloa Village, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,858 ($408/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
- $5,366 ($767/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($673/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Oct 7–14, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,535 ($362/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
WorldMark Kona Resort
Kailua-Kona, Hawaii- Oct 7–14, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,428 ($347/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 11–17, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,404 ($567/night)
Verified & Protected
Pono Kai
Kapaa, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/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
- $6,456 ($922/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
- $5,475 ($782/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Kona Coast Resort
Kailua-Kona, Hawaii- Oct 10–14, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,878 ($470/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
- $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
- $5,748 ($821/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
- $3,022 ($302/night)
Verified & Protected
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/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
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)