Winter Timeshare Rentals in Florida

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 4–7, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$439 ($146/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,750 ($393/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
$2,696 ($385/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 5
$4,498 ($643/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,614 ($373/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
$5,366 ($767/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,600 ($514/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–9, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$870 ($218/night)

The Galleon Resort

Key West, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,930 ($704/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
$4,058 ($580/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
$2,804 ($401/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–19, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$2,161 ($154/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
$4,551 ($650/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$995 ($142/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–9, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$555 ($139/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–9, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$427 ($107/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$746 ($107/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
$5,366 ($767/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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–19, 2026 (14 nights)
3 bed/2 bath, sleeps 10
$3,087 ($220/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
$3,175 ($454/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–8, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$684 ($228/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$1,550 ($221/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 5–11, 2026 (6 nights)
Studio/1 bath, sleeps 4
$2,292 ($382/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–19, 2026 (14 nights)
1 bed/1 bath, sleeps 4
$1,507 ($108/night)

Hyatt Windward Pointe Resort

Key West, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,840 ($549/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–14, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$999 ($111/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–10, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$499 ($100/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–8, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$451 ($150/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–8, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$355 ($118/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–10, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$1,057 ($211/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,022 ($604/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–9, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$271 ($90/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–19, 2026 (13 nights)
1 bed/1 bath, sleeps 4
$1,202 ($92/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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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,022 ($604/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–9, 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 6–9, 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 6–11, 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 6–12, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$573 ($95/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$932 ($186/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–19, 2026 (13 nights)
2 bed/2 bath, sleeps 8
$2,432 ($187/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)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–19, 2026 (13 nights)
2 bed/2 bath, sleeps 8
$2,842 ($219/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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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,022 ($604/night)

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
Studio/1 bath, sleeps 4
$2,990 ($598/night)