Winter Timeshare Rentals in Florida

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Marriott's Grande Vista

Orlando, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/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
$817 ($163/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 3, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,145 ($191/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
$1,387 ($198/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 3, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,163 ($194/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28–31, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$271 ($90/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$415 ($83/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28–31, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$415 ($138/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 Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$955 ($191/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 3, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$626 ($104/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)
1 bed/1 bath, sleeps 4
$710 ($178/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28–31, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$719 ($240/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,295 ($259/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 1, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$764 ($191/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$977 ($195/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,295 ($185/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 5, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$1,585 ($198/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 Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 5, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$1,295 ($162/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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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
Studio/1 bath, sleeps 4
$2,615 ($523/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 9, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$2,554 ($213/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 9, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$2,048 ($171/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$781 ($195/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 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 Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$343 ($86/night)

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Marriott Vacation Club Pulse, South Beach

Miami Beach, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
Studio/1 bath, sleeps 3
$2,750 ($550/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$733 ($105/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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 3, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,629 ($272/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$523 ($105/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 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 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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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 Ocean Walk

Daytona Beach, Florida

Dec 29, 2026 – Jan 2, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$781 ($195/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 Ocean Walk

Daytona Beach, Florida

Dec 29, 2026 – Jan 2, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$764 ($191/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 Ocean Walk

Daytona Beach, Florida

Dec 29, 2026 – Jan 2, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$343 ($86/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)