Columbus Day Timeshare Rentals in Florida

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
$2,750 ($393/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 12–19, 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 12–19, 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 12–19, 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 12–19, 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 12–19, 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 5–14, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$2,068 ($230/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 5–14, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,383 ($154/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 5–14, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$2,068 ($230/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 5–14, 2026 (9 nights)
2 bed/2 bath, sleeps 6
$2,528 ($281/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 5–14, 2026 (9 nights)
3 bed/2 bath, sleeps 10
$2,528 ($281/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,428 ($347/night)

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Sheraton Vistana Resort

Orlando, Florida

Oct 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,330 ($190/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 11–18, 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 11–18, 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 12–17, 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 12–17, 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 12–17, 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 12–17, 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 12–17, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$759 ($152/night)

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Hyatt Sunset Harbor Resort

Key West, Florida

Oct 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,404 ($486/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 7–13, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,475 ($246/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 7–13, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$986 ($164/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 7–13, 2026 (6 nights)
3 bed/2 bath, sleeps 10
$1,795 ($299/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 7–13, 2026 (6 nights)
2 bed/2 bath, sleeps 6
$1,795 ($299/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 7–13, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,475 ($246/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Oct 12–16, 2026 (4 nights)
Studio/1 bath, sleeps 5
$2,222 ($556/night)

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Disney's Animal Kingdom Villas - Jambo House

Lake Buena Vista, Florida

Oct 12–17, 2026 (5 nights)
Studio/1 bath, sleeps 4
$2,509 ($502/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,660 ($237/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 11–17, 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 11–17, 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 11–17, 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 11–17, 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 11–17, 2026 (6 nights)
2 bed/2 bath, sleeps 6
$1,642 ($274/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)
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
$1,251 ($156/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 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)
2 bed/2 bath, sleeps 6
$2,283 ($285/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 11–25, 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)
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 11–15, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$804 ($201/night)