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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Club Wyndham Cypress Palms
Kissimmee, Florida- Oct 5–14, 2026 (9 nights)
- 2 bed/2 bath, sleeps 8
- $1,576 ($175/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Oct 12–18, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,207 ($201/night)
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Marriott Vacation Club Pulse, South Beach
Miami Beach, Florida- Oct 10–15, 2026 (5 nights)
- Studio/1 bath, sleeps 5
- $2,423 ($485/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Oct 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,968 ($424/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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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
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Marriott's Grande Vista
Orlando, Florida- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,440 ($206/night)
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The Galleon Resort
Key West, Florida- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($564/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
- $1,824 ($260/night)
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Sanibel Beach Club
Sanibel Island, Florida- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,772 ($253/night)
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Holiday Inn Club Vacations Panama City Beach Resort
Panama City Beach, Florida- Oct 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,260 ($323/night)
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Coral Reef Beach Resort
St. Pete Beach, Florida- Oct 10–17, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Oct 10–16, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,450 ($408/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Oct 8–13, 2026 (5 nights)
- 2 bed/2 bath, sleeps 9
- $6,020 ($1,204/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
- $3,404 ($486/night)
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Holiday Inn Club Vacations at Orange Lake Resort - East Village
Kissimmee, Florida- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
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Westgate Lakes Resort & Spa
Orlando, Florida- Oct 9–16, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,291 ($327/night)
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Westgate Lakes Resort & Spa
Orlando, Florida- Oct 9–16, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $1,866 ($267/night)
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Westgate Town Center
Kissimmee, Florida- Oct 9–16, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
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Westgate Lakes Resort & Spa
Orlando, Florida- Oct 10–17, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $1,866 ($267/night)
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Westgate Town Center
Kissimmee, Florida- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,536 ($219/night)
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Westgate Town Center
Kissimmee, Florida- Oct 9–16, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
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Westgate Town Center
Kissimmee, Florida- Oct 9–16, 2026 (7 nights)
- 5 bed/5 bath, sleeps 20
- $2,531 ($362/night)
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Westgate Town Center
Kissimmee, Florida- Oct 9–16, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Oct 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Oct 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/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
- $2,696 ($385/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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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Oct 12–15, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $603 ($201/night)
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CHOOSE YOUR OWN DATES
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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Club Wyndham Cypress Palms
Kissimmee, Florida- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Oct 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/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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Caloosa Cove Resort
Islamorada, Florida- Oct 10–17, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $1,550 ($221/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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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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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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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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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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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)
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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)