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
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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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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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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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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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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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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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
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 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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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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Maui Schooner
Kihei, Hawaii- Oct 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/night)
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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)
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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)
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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)
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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
- $5,475 ($782/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Oct 10–17, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $15,285 ($2,184/night)