Winter Timeshare Rentals in Florida

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 6–18, 2027 (12 nights)
2 bed/2 bath, sleeps 6
$3,565 ($297/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 6–10, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$694 ($173/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Jan 8–15, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$1,893 ($270/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 8–11, 2027 (3 nights)
3 bed/3 bath, sleeps 10
$3,622 ($1,207/night)

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Westgate Palace

Orlando, Florida

Jan 8–15, 2027 (7 nights)
2 bed/2 bath, sleeps 4
$1,190 ($170/night)

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Eagle's Nest Beach Resort

Marco Island, Florida

Jan 8–15, 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

Jan 8–15, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,673 ($239/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–15, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,673 ($239/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–15, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,119 ($160/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–15, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,039 ($291/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Jan 8–15, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,984 ($712/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–15, 2027 (7 nights)
3 bed/2 bath, sleeps 10
$2,039 ($291/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,673 ($239/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Jan 9–16, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,309 ($330/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,179 ($740/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (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

Jan 9–16, 2027 (7 nights)
3 bed/2 bath, sleeps 10
$2,039 ($291/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,821 ($689/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–16, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,673 ($239/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,039 ($291/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 9–23, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$2,701 ($193/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 9–23, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$1,849 ($132/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (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

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,748 ($821/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 9–12, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$331 ($110/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–16, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,119 ($160/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,455 ($922/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 9–12, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$427 ($142/night)

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The Banyan Resort

Key West, Florida

Jan 9–16, 2027 (7 nights)
Studio/1 bath, sleeps 2
$2,423 ($346/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 9–23, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,489 ($249/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 9–12, 2027 (3 nights)
2 bed/2 bath, sleeps 8
$604 ($201/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 9–12, 2027 (3 nights)
2 bed/2 bath, sleeps 8
$719 ($240/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Jan 9–16, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,831 ($404/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,085 ($869/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,766 ($681/night)

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Marriott's Villas at Doral

Miami, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,320 ($903/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Jan 9–15, 2027 (6 nights)
Studio/1 bath, sleeps 4
$2,150 ($358/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 10–16, 2027 (6 nights)
3 bed/3 bath, sleeps 10
$6,892 ($1,149/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 10–17, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,638 ($806/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 10–17, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,112 ($588/night)

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Copper Creek Villas & Cabins at Disney's Wilderness Lodge

Lake Buena Vista, Florida

Jan 10–13, 2027 (3 nights)
Studio/1 bath, sleeps 4
$1,346 ($449/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 10–17, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,456 ($922/night)

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Hyatt Beach House Resort

Key West, Florida

Jan 10–17, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,513 ($502/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Jan 10–17, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,458 ($494/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Jan 10–15, 2027 (5 nights)
Studio/1 bath, sleeps 4
$1,462 ($292/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Jan 10–17, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,077 ($440/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 10–17, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,603 ($658/night)