Winter Timeshare Rentals in Florida

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 10, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,993 ($285/night)

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Palm Beach Shores Resort and Vacation Villas

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,314 ($331/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,513 ($502/night)

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Club Wyndham Sea Gardens

Pompano Beach, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,439 ($240/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,476 ($211/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
$7,000 ($1,000/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 27–31, 2026 (4 nights)
Studio/1 bath, sleeps 5
$3,478 ($870/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)

Hyatt Sunset Harbor Resort

Key West, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 2
$4,930 ($704/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)

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
$10,216 ($1,460/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 Ocean Walk

Daytona Beach, Florida

Dec 27, 2026 – Jan 4, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$924 ($115/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
$6,891 ($984/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 27, 2026 – Jan 4, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$1,524 ($190/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$4,688 ($670/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,777 ($682/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
$8,526 ($1,218/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
$4,766 ($681/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$487 ($81/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)

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
$9,616 ($1,374/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,532 ($362/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
$9,180 ($1,311/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 27, 2026 – Jan 2, 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 27, 2026 – Jan 2, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,172 ($195/night)

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Club Wyndham Santa Barbara

Pompano Beach, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,685 ($384/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 5
$5,440 ($777/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,222 ($603/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$4,603 ($767/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)

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
$7,654 ($1,093/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$4,688 ($670/night)

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Vistana Beach Club

Jensen Beach, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$4,603 ($658/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
$5,284 ($755/night)

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Palm Beach Shores Resort and Vacation Villas

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,410 ($344/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 27–31, 2026 (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 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,865 ($266/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
$8,417 ($1,202/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,524 ($218/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 Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,202 ($172/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
$9,181 ($1,312/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
$9,181 ($1,312/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,529 ($218/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
$8,418 ($1,203/night)