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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Marriott's Oceana Palms
Riviera Beach, Florida- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($517/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($517/night)
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Plantation Beach Club at Indian River
Stuart, Florida- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,095 ($299/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,382 ($483/night)
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Plantation House at South Seas Island Resort
Captiva, Florida- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,189 ($313/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 4–16, 2026 (12 nights)
- 2 bed/2 bath, sleeps 8
- $3,618 ($301/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Oct 11–17, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,207 ($201/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Oct 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,399 ($343/night)
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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 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)
- 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
- $415 ($138/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)
- 2 bed/2 bath, sleeps 8
- $1,271 ($318/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 9–14, 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 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 1–15, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $4,102 ($293/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 Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 8–22, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $4,201 ($300/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)
- 2 bed/2 bath, sleeps 8
- $4,201 ($300/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)
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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)
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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)
- 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)
- 2 bed/2 bath, sleeps 8
- $1,194 ($298/night)
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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)
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Club Sevilla
Kissimmee, Florida- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,165 ($166/night)
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Marriott's Grande Vista
Orlando, Florida- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,878 ($268/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,113 ($302/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 4–17, 2026 (13 nights)
- 2 bed/2 bath, sleeps 8
- $3,870 ($298/night)
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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 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 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,113 ($302/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
- $2,113 ($302/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 12–17, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,528 ($306/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($455/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
- $1,860 ($310/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 8
- $1,385 ($198/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
- $1,779 ($296/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)