Winter Timeshare Rentals in Florida

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
$5,638 ($806/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–12, 2027 (3 nights)
2 bed/2 bath, sleeps 8
$935 ($312/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 Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–12, 2027 (3 nights)
3 bed/2 bath, sleeps 10
$901 ($300/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–12, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$739 ($246/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–23, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$2,222 ($159/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)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–23, 2027 (14 nights)
3 bed/2 bath, sleeps 10
$4,054 ($290/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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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 Ocean Walk

Daytona Beach, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,365 ($195/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 9–15, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$693 ($115/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 9–16, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$808 ($115/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
$2,153 ($308/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
$6,455 ($922/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–12, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$499 ($166/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
$5,038 ($720/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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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 9–15, 2027 (6 nights)
3 bed/3 bath, sleeps 10
$4,162 ($694/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
$5,179 ($740/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,840 ($549/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,334 ($191/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 10–16, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$892 ($149/night)

Hyatt Sunset Harbor Resort

Key West, Florida

Jan 10–14, 2027 (4 nights)
Studio/1 bath, sleeps 2
$1,330 ($332/night)

Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 10–17, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,020 ($860/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 10–16, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$693 ($115/night)

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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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Jan 10–16, 2027 (6 nights)
Studio/1 bath, sleeps 5
$3,230 ($538/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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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Jan 10–17, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,183 ($312/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Jan 10–14, 2027 (4 nights)
Studio/1 bath, sleeps 5
$2,379 ($595/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Jan 10–17, 2027 (7 nights)
Studio/1 bath, sleeps 5
$4,224 ($603/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Jan 10–17, 2027 (7 nights)
Studio/1 bath, sleeps 5
$3,840 ($549/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Jan 10–16, 2027 (6 nights)
Studio/1 bath, sleeps 5
$2,505 ($417/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Jan 10–16, 2027 (6 nights)
Studio/1 bath, sleeps 4
$1,987 ($331/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Jan 10–15, 2027 (5 nights)
Studio/1 bath, sleeps 5
$2,314 ($463/night)

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Copper Creek Villas & Cabins at Disney's Wilderness Lodge

Lake Buena Vista, Florida

Jan 10–16, 2027 (6 nights)
Studio/1 bath, sleeps 4
$3,298 ($550/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Jan 10–15, 2027 (5 nights)
Studio/1 bath, sleeps 5
$2,712 ($542/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Jan 10–16, 2027 (6 nights)
Studio/1 bath, sleeps 5
$2,802 ($467/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)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 10–16, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,339 ($223/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 10–16, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,821 ($304/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 10–16, 2027 (6 nights)
3 bed/2 bath, sleeps 10
$1,642 ($274/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 10–16, 2027 (6 nights)
2 bed/2 bath, sleeps 6
$1,642 ($274/night)