Winter Timeshare Rentals in Florida

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Hyatt Sunset Harbor Resort

Key West, Florida

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,167 ($595/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–18, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$577 ($115/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–20, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$2,057 ($294/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–16, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$559 ($186/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$986 ($141/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–18, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$1,082 ($216/night)

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Hyatt Sunset Harbor Resort

Key West, Florida

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,167 ($595/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–16, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$271 ($90/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Dec 13–17, 2026 (4 nights)
2 bed/2 bath, sleeps 6
$1,878 ($470/night)

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Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,696 ($385/night)

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Vacation Village at Parkway

Kissimmee, Florida

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,286 ($184/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–19, 2026 (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 13–19, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$972 ($162/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–18, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$415 ($83/night)

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Holiday Inn Club Vacations Marco Island - Sunset Cove Resort

Marco Island, Florida

Dec 13–18, 2026 (5 nights)
3 bed/2 bath, sleeps 8
$2,204 ($441/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,638 ($234/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–19, 2026 (6 nights)
3 bed/2 bath, sleeps 10
$1,497 ($250/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,365 ($195/night)

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Marriott's Crystal Shores

Marco Island, Florida

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,886 ($412/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 13–19, 2026 (6 nights)
Studio/1 bath, sleeps 4
$2,903 ($484/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 13–18, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$932 ($186/night)

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Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,077 ($440/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–26, 2026 (12 nights)
2 bed/2 bath, sleeps 8
$2,685 ($224/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 14–20, 2026 (6 nights)
Studio/1 bath, sleeps 4
$1,220 ($203/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–26, 2026 (12 nights)
1 bed/1 bath, sleeps 4
$1,141 ($95/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 14–20, 2026 (6 nights)
Studio/1 bath, sleeps 4
$1,220 ($203/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 14–19, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$1,312 ($262/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 14–17, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$271 ($90/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–26, 2026 (12 nights)
2 bed/2 bath, sleeps 8
$2,305 ($192/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 14–17, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$367 ($122/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 14–19, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$857 ($171/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 14–19, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$613 ($123/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–26, 2026 (12 nights)
1 bed/1 bath, sleeps 4
$1,563 ($130/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 14–17, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$559 ($186/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 14–21, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,339 ($477/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 15–25, 2026 (10 nights)
1 bed/1 bath, sleeps 4
$1,251 ($125/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 15–25, 2026 (10 nights)
2 bed/2 bath, sleeps 8
$2,135 ($214/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 15–19, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$1,128 ($282/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 15–17, 2026 (2 nights)
Studio/1 bath, sleeps 5
$1,895 ($948/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 15–22, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$977 ($140/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Dec 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 15–25, 2026 (10 nights)
1 bed/1 bath, sleeps 4
$897 ($90/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 15–19, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$741 ($185/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 15–25, 2026 (10 nights)
2 bed/2 bath, sleeps 8
$1,839 ($184/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,392 ($199/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,830 ($261/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 15–19, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$535 ($134/night)