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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Hyatt Sunset Harbor Resort
Key West, Florida- Oct 11–15, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,824 ($456/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 8–16, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,251 ($156/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 11–25, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,118 ($151/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 11–15, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($134/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 11–15, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $804 ($201/night)
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Hyatt Pinon Pointe
Sedona, Arizona- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 10–15, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $759 ($152/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 11–16, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 11–16, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/night)
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Voted Top Pick 2026
Marriott's Desert Springs Villas II
Palm Desert, California- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 10–16, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,779 ($296/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 10–16, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $892 ($149/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 10–16, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,339 ($223/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,443 ($289/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Oct 11–18, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,077 ($440/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 9–22, 2026 (13 nights)
- 1 bed/1 bath, sleeps 4
- $2,092 ($161/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,113 ($302/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Oct 9–14, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($310/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
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Marriott's Harbour Point and Sunset Pointe at Shelter Cove
Hilton Head Island, South Carolina- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Oct 11–16, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,576 ($515/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 8–14, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $986 ($164/night)
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Desert Springs Villas II
Palm Desert, California- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
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La Cabana Beach Resort
Oranjestad, Aruba- Oct 9–16, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,768 ($253/night)
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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)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Oct 9–16, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,532 ($362/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($673/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Oct 10–17, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Oct 9–16, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,495 ($214/night)
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The Westin Los Cabos Resort Villas & Spa
San Jose del Cabo, Mexico- Oct 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Oct 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,233 ($462/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Oct 9–16, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,535 ($362/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,619 ($374/night)
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Marriott's Summit Watch
Park City, Utah- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,361 ($766/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Oct 10–17, 2026 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $3,731 ($533/night)
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Marriott's Shadow Ridge - The Villages
Palm Desert, California- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($412/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Oct 11–17, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $3,653 ($609/night)
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Grand Lodge on Peak 7
Breckenridge, Colorado- Oct 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,150 ($307/night)