Winter Timeshare Rentals in Florida

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$710 ($178/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 9, 2027 (12 nights)
1 bed/1 bath, sleeps 4
$1,356 ($113/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28–31, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$535 ($178/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$959 ($240/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 5, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$839 ($105/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$937 ($187/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,923 ($275/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$990 ($198/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 3, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$693 ($115/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 3, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$487 ($81/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28–31, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$463 ($154/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,136 ($162/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$559 ($80/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,334 ($191/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 1, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$1,297 ($432/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,251 ($179/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,365 ($195/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,420 ($774/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,980 ($283/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 2, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$759 ($190/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 2, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$1,057 ($264/night)

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Marriott's Crystal Shores

Marco Island, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,418 ($1,203/night)

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Marriott's Crystal Shores

Marco Island, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 4, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,687 ($281/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 29, 2026 – Jan 4, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,238 ($206/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 4, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,119 ($186/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$808 ($115/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 29, 2026 – Jan 4, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,003 ($167/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 29, 2026 – Jan 4, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$653 ($109/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 30, 2026 – Jan 2, 2027 (3 nights)
2 bed/2 bath, sleeps 8
$1,987 ($662/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 3, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$808 ($202/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 3, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$1,154 ($288/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 4, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,450 ($290/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 6, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,207 ($172/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 2, 2027 (3 nights)
2 bed/2 bath, sleeps 8
$817 ($272/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 4, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$941 ($188/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 5, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,745 ($291/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 2, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$582 ($194/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 6, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,038 ($291/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 30, 2026 – Jan 4, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$870 ($174/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 5, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,074 ($179/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 30, 2026 – Jan 4, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,088 ($218/night)

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Disney's Riviera Resort

Lake Buena Vista, Florida

Dec 31, 2026 – Jan 2, 2027 (2 nights)
Studio/1 bath, sleeps 5
$1,509 ($755/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 31, 2026 – Jan 4, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$764 ($191/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 31, 2026 – Jan 4, 2027 (4 nights)
3 bed/2 bath, sleeps 10
$1,374 ($344/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 31, 2026 – Jan 7, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$559 ($80/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 31, 2026 – Jan 7, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,163 ($166/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 31, 2026 – Jan 7, 2027 (7 nights)
3 bed/2 bath, sleeps 10
$2,109 ($301/night)