Winter Timeshare Rentals in Florida

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Holiday Inn Club Vacations Marco Island - Sunset Cove Resort

Marco Island, Florida

Jan 16–23, 2027 (7 nights)
3 bed/2 bath, sleeps 8
$3,076 ($439/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 16–23, 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 16–30, 2027 (14 nights)
3 bed/2 bath, sleeps 10
$4,054 ($290/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Jan 17–20, 2027 (3 nights)
Studio/1 bath, sleeps 5
$1,581 ($527/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–20, 2027 (3 nights)
3 bed/2 bath, sleeps 10
$746 ($249/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 17–24, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,802 ($829/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–24, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,153 ($308/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Jan 17–22, 2027 (5 nights)
Studio/1 bath, sleeps 4
$1,578 ($316/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–20, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$603 ($201/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–25, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$1,870 ($234/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–24, 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 17–21, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$1,194 ($298/night)

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Jan 17–22, 2027 (5 nights)
Studio/1 bath, sleeps 4
$2,576 ($515/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Jan 17–23, 2027 (6 nights)
Studio/1 bath, sleeps 4
$1,987 ($331/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–31, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$2,222 ($159/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–25, 2027 (8 nights)
3 bed/2 bath, sleeps 10
$2,283 ($285/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–21, 2027 (4 nights)
3 bed/2 bath, sleeps 10
$995 ($249/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Jan 17–22, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$2,472 ($494/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–21, 2027 (4 nights)
2 bed/2 bath, sleeps 6
$995 ($249/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–22, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$666 ($133/night)

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The Villas at Disney's Grand Floridian Resort & Spa

Lake Buena Vista, Florida

Jan 17–20, 2027 (3 nights)
Studio/1 bath, sleeps 5
$1,637 ($546/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–25, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$1,251 ($156/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–23, 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 17–23, 2027 (6 nights)
2 bed/2 bath, sleeps 6
$1,642 ($274/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–20, 2027 (3 nights)
2 bed/2 bath, sleeps 8
$896 ($299/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–25, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,446 ($306/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–25, 2027 (8 nights)
2 bed/2 bath, sleeps 6
$2,283 ($285/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–23, 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 17–24, 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 17–24, 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 17–22, 2027 (5 nights)
2 bed/2 bath, sleeps 6
$4,057 ($811/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Jan 17–23, 2027 (6 nights)
Studio/1 bath, sleeps 5
$3,596 ($599/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–31, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$3,321 ($237/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–31, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$4,280 ($306/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–31, 2027 (14 nights)
3 bed/2 bath, sleeps 10
$4,054 ($290/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Jan 17–21, 2027 (4 nights)
2 bed/2 bath, sleeps 6
$1,834 ($459/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–21, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$804 ($201/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–22, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,488 ($298/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–20, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$415 ($138/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–22, 2027 (5 nights)
3 bed/2 bath, sleeps 10
$1,242 ($248/night)

Hyatt Beach House Resort

Key West, Florida

Jan 17–24, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,295 ($471/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–22, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$1,003 ($201/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–21, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$535 ($134/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 17–24, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–22, 2027 (5 nights)
2 bed/2 bath, sleeps 6
$1,242 ($248/night)

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Jan 17–21, 2027 (4 nights)
Studio/1 bath, sleeps 4
$1,987 ($497/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Jan 17–22, 2027 (5 nights)
Studio/1 bath, sleeps 4
$1,660 ($332/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 17–20, 2027 (3 nights)
2 bed/2 bath, sleeps 6
$746 ($249/night)