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
- $6,107 ($872/night)
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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)
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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
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
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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)
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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
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,804 ($401/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 11–18, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,791 ($1,113/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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The Cliffs at Princeville
Princeville, Hawaii- Oct 11–18, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,423 ($346/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,932 ($276/night)
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Paniolo Greens
Waikoloa Village, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($221/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Oct 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,636 ($377/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Oct 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 7–13, 2026 (6 nights)
- Studio/1 bath, sleeps 2
- $1,440 ($240/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 7–14, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,368 ($338/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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Kalia Suites by Hilton Grand Vacations
Honolulu, Hawaii- Oct 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,150 ($307/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,756 ($537/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,749 ($393/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)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,532 ($362/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,077 ($440/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,764 ($538/night)