Winter Timeshare Rentals in Florida

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,365 ($195/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$799 ($114/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,339 ($191/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$2,886 ($577/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,527 ($1,218/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27–31, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$790 ($198/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$559 ($80/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 27, 2026 – Jan 3, 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 27–31, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$710 ($178/night)

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Hyatt Beach House Resort

Key West, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$5,039 ($720/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,147 ($735/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27–31, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$427 ($107/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$4,276 ($611/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,932 ($386/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 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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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 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 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 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 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 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 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 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 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 Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$577 ($115/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 2, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$937 ($187/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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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 28–31, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$415 ($138/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, 2026 – Jan 5, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$839 ($105/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 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, 2026 – Jan 4, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$733 ($105/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 Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 3, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,172 ($195/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 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 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, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,136 ($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)