Columbus Day Timeshare Rentals in Florida

Hyatt Sunset Harbor Resort

Key West, Florida

Oct 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,513 ($502/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,840 ($549/night)

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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 8–16, 2026 (8 nights)
2 bed/2 bath, sleeps 6
$2,283 ($285/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 8–16, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,870 ($234/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
$1,870 ($234/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 8–16, 2026 (8 nights)
3 bed/2 bath, sleeps 10
$2,283 ($285/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
$3,068 ($219/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 11–25, 2026 (14 nights)
2 bed/2 bath, sleeps 6
$3,871 ($276/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 11–25, 2026 (14 nights)
3 bed/2 bath, sleeps 10
$3,871 ($276/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 11–25, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$3,068 ($219/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 11–15, 2026 (4 nights)
2 bed/2 bath, sleeps 6
$995 ($249/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)
2 bed/2 bath, sleeps 8
$804 ($201/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 11–15, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$995 ($249/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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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 10–15, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,141 ($228/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 10–15, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,141 ($228/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 10–15, 2026 (5 nights)
2 bed/2 bath, sleeps 6
$1,396 ($279/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 10–15, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$1,396 ($279/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)
3 bed/2 bath, sleeps 10
$1,242 ($248/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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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 10–16, 2026 (6 nights)
3 bed/2 bath, sleeps 10
$1,642 ($274/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)
2 bed/2 bath, sleeps 6
$1,642 ($274/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
$1,339 ($223/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
$1,003 ($201/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 6
$1,242 ($248/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 9–22, 2026 (13 nights)
2 bed/2 bath, sleeps 8
$3,125 ($240/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 9–22, 2026 (13 nights)
1 bed/1 bath, sleeps 4
$3,125 ($240/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 9–22, 2026 (13 nights)
3 bed/2 bath, sleeps 10
$3,809 ($293/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 9–22, 2026 (13 nights)
2 bed/2 bath, sleeps 6
$3,809 ($293/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 10–17, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$2,039 ($291/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 6
$2,039 ($291/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
$1,673 ($239/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)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Oct 9–14, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,660 ($332/night)

Verified & Protected

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)