Winter Timeshare Rentals in Florida

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Blue Tree Resort at Lake Buena Vista

Orlando, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$760 ($109/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,968 ($424/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,222 ($603/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,535 ($505/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,365 ($195/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,404 ($486/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$684 ($98/night)

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Grand Beach Resort

Orlando, Florida

Dec 5–12, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$1,660 ($237/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 6–13, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$777 ($111/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,535 ($505/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 6–11, 2026 (5 nights)
Studio/1 bath, sleeps 4
$1,522 ($304/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 6–11, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,605 ($321/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–17, 2026 (11 nights)
2 bed/2 bath, sleeps 8
$1,996 ($181/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 6–12, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,092 ($182/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,290 ($470/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–17, 2026 (11 nights)
1 bed/1 bath, sleeps 4
$968 ($88/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 6–12, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$573 ($95/night)

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Hilton Grand Vacations at SeaWorld

Orlando, Florida

Dec 6–13, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$2,478 ($354/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–11, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$2,531 ($506/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–12, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,083 ($181/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–12, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$523 ($87/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–12, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,251 ($208/night)

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Vacation Village at Parkway

Kissimmee, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,385 ($198/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,886 ($412/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–17, 2026 (11 nights)
2 bed/2 bath, sleeps 8
$2,310 ($210/night)

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Silver Lake Resort

Kissimmee, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 6–12, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$892 ($149/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,568 ($510/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,330 ($190/night)

Hyatt Sunset Harbor Resort

Key West, Florida

Dec 6–13, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,268 ($467/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 7–10, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$559 ($186/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 7–12, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$759 ($152/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 7–10, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$367 ($122/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 7–14, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$755 ($108/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 7–12, 2026 (5 nights)
3 bed/3 bath, sleeps 10
$2,750 ($550/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 7–14, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,444 ($206/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 7–11, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$343 ($86/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 7–11, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$604 ($151/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 7–12, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$499 ($100/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 7–11, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$535 ($134/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 7–11, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$471 ($118/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 7–14, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,127 ($161/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 7–12, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$941 ($188/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 8–22, 2026 (14 nights)
1 bed/1 bath, sleeps 4
$1,365 ($98/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 8–22, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$3,199 ($229/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 8–22, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$2,711 ($194/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 9–12, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$355 ($118/night)