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.
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Oct 10–16, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($277/night)
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
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)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/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
- $3,431 ($490/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
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)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,202 ($743/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
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,294 ($471/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 10–15, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $1,550 ($310/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 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 11–18, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,091 ($1,156/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/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
- $3,077 ($440/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Oct 11–18, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,314 ($331/night)
Verified & Protected
Paniolo Greens
Waikoloa Village, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($221/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
- $3,497 ($500/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
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Oct 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,854 ($408/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/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
Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Oct 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Oct 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,039 ($720/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 7–13, 2026 (6 nights)
- Studio/1 bath, sleeps 2
- $2,532 ($422/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/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
- $2,642 ($377/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Oct 7–14, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,423 ($346/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
Kalia Suites by Hilton Grand Vacations
Honolulu, Hawaii- Oct 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,418 ($345/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,832 ($547/night)
Verified & Protected
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)
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
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)
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
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Oct 7–13, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($604/night)
Verified & Protected
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)
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)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)