Winter Timeshare Rentals in Florida

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 7–11, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$343 ($86/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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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 7–13, 2026 (6 nights)
Studio/1 bath, sleeps 4
$2,390 ($398/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 7–14, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$995 ($142/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 7–14, 2026 (7 nights)
Studio/1 bath, sleeps 5
$4,498 ($643/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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 7–11, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$746 ($186/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 8–11, 2026 (3 nights)
2 bed/2 bath, sleeps 6
$559 ($186/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 8–13, 2026 (5 nights)
2 bed/2 bath, sleeps 6
$1,180 ($236/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 8–11, 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 8–11, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$559 ($186/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 8–15, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 8–13, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$1,180 ($236/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 8–13, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$586 ($117/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 8–15, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

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

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 9–23, 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 9–23, 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 9–23, 2026 (14 nights)
1 bed/1 bath, sleeps 4
$1,856 ($133/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 9–13, 2026 (4 nights)
2 bed/2 bath, sleeps 6
$995 ($249/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 9–12, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$451 ($150/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 9–23, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$2,711 ($194/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 9–13, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$511 ($128/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 9–13, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$995 ($249/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 9–12, 2026 (3 nights)
2 bed/2 bath, sleeps 6
$684 ($228/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 9–12, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$684 ($228/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 9–16, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,622 ($517/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,306 ($472/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$586 ($117/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,949 ($564/night)

DiamondHead Beach Resort

Fort Myers Beach, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,768 ($253/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
2 bed/2 bath, sleeps 6
$1,180 ($236/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–14, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$439 ($146/night)

Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–19, 2026 (8 nights)
2 bed/2 bath, sleeps 6
$2,109 ($264/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,295 ($471/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–19, 2026 (8 nights)
3 bed/2 bath, sleeps 10
$2,109 ($264/night)

DiamondHead Beach Resort

Fort Myers Beach, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,123 ($303/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,077 ($615/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,077 ($615/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,749 ($393/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–19, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,039 ($130/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–19, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,012 ($127/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,314 ($331/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$1,180 ($236/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$764 ($153/night)