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
$3,633 ($519/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 9–17, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,484 ($311/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 9–17, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$2,004 ($251/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 9–17, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,343 ($168/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 9–17, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,769 ($221/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 8–13, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,506 ($301/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 8–13, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$786 ($157/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 8–13, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,145 ($229/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 7–21, 2026 (14 nights)
1 bed/1 bath, sleeps 4
$2,222 ($159/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 7–21, 2026 (14 nights)
1 bed/1 bath, sleeps 4
$3,321 ($237/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 7–21, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$4,280 ($306/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 12–15, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$746 ($249/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 12–15, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$896 ($299/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 12–15, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$603 ($201/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 12–15, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$415 ($138/night)

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The Galleon Resort

Key West, Florida

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,513 ($502/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 9–16, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,026 ($147/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 9–16, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,948 ($278/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Oct 9–16, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,488 ($213/night)

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Casa Ybel Resort

Sanibel Island, Florida

Oct 9–16, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,314 ($331/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 8–13, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,566 ($313/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 9–13, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,077 ($269/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 9–13, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$703 ($176/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 9–13, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,271 ($318/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 9–16, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,063 ($152/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 9–16, 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 9–14, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$852 ($170/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 10–14, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$626 ($157/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 10–14, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,232 ($308/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 10–14, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$940 ($235/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 1–15, 2026 (14 nights)
1 bed/1 bath, sleeps 4
$2,170 ($155/night)

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Caloosa Cove Resort

Islamorada, Florida

Oct 10–17, 2026 (7 nights)
Studio/1 bath, sleeps 3
$1,660 ($237/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Oct 10–13, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$427 ($142/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Oct 10–13, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$604 ($201/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 3–17, 2026 (14 nights)
1 bed/1 bath, sleeps 4
$2,222 ($159/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 3–17, 2026 (14 nights)
1 bed/1 bath, sleeps 4
$3,321 ($237/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 8–18, 2026 (10 nights)
1 bed/1 bath, sleeps 4
$2,533 ($253/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 8–18, 2026 (10 nights)
1 bed/1 bath, sleeps 4
$1,699 ($170/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 8–18, 2026 (10 nights)
2 bed/2 bath, sleeps 8
$3,109 ($311/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Oct 10–17, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,467 ($352/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Oct 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,458 ($494/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 12–16, 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 12–16, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,194 ($298/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Oct 12–16, 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 12–16, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$804 ($201/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
$3,840 ($549/night)

Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Oct 12–26, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$3,840 ($274/night)

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Club Sevilla

Kissimmee, Florida

Oct 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,165 ($166/night)