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.
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,428 ($632/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,382 ($626/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Oct 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 2
- $1,894 ($271/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 10–19, 2026 (9 nights)
- 2 bed/2 bath, sleeps 6
- $4,341 ($482/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($550/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 11–21, 2026 (10 nights)
- 2 bed/2 bath, sleeps 6
- $4,472 ($447/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 9–13, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,839 ($460/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 9–13, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,118 ($529/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,816 ($831/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 9–17, 2026 (8 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($494/night)
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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)
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The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,967 ($424/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($397/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,462 ($487/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,268 ($423/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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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
- $4,069 ($581/night)
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Kamaole Beach Club
Kihei, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 10–16, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($440/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Club Wyndham Ka 'Eo Kai
Princeville, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,531 ($362/night)
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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)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,855 ($694/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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WorldMark Kona Resort
Kailua-Kona, Hawaii- Oct 7–14, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,428 ($347/night)
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Pono Kai
Kapaa, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
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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)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,175 ($739/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Kona Coast Resort
Kailua-Kona, Hawaii- Oct 10–14, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,220 ($305/night)
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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)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,137 ($734/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,137 ($734/night)
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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
- $4,984 ($712/night)
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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)
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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)
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Wyndham Kauai Coast Resort at the Beachboy
Kapaa, Hawaii- Oct 9–19, 2026 (10 nights)
- 1 bed/1 bath, sleeps 4
- $2,804 ($280/night)
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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)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Maui Schooner
Kihei, Hawaii- Oct 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/night)