Winter Timeshare Rentals in Florida

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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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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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 27–30, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$573 ($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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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
$3,186 ($455/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)

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
$5,910 ($844/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 Ocean Walk

Daytona Beach, Florida

Dec 27–30, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$367 ($122/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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Marriott's Grande Vista

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/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
$3,622 ($517/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)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$9,018 ($1,503/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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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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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 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 Ocean Walk

Daytona Beach, Florida

Dec 27–30, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$271 ($90/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 27–30, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$719 ($240/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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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)

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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Vistana Beach Club

Jensen Beach, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,077 ($440/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,114 ($186/night)

Vistana Beach Club

Jensen Beach, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,750 ($393/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
$3,290 ($470/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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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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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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The Villas at Disney's Grand Floridian Resort & Spa

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 5
$13,105 ($1,872/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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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,385 ($626/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
$3,949 ($564/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
$4,276 ($611/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, 2026 – Jan 1, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$888 ($178/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
$1,559 ($195/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 4, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,158 ($270/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)

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
$8,723 ($1,246/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 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
$8,417 ($1,202/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27–31, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$626 ($157/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)