Winter Timeshare Rentals in Florida

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Hyatt Sunset Harbor Resort

Key West, Florida

Dec 24–27, 2026 (3 nights)
2 bed/2.5 bath, sleeps 6
$2,423 ($808/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,978 ($283/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 24–28, 2026 (4 nights)
Studio/1 bath, sleeps 4
$2,532 ($633/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 24–31, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,840 ($549/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–28, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$941 ($235/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–27, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$1,030 ($343/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–27, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$1,030 ($343/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–27, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$764 ($255/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–29, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$2,478 ($496/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–31, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,655 ($1,094/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 24–31, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$986 ($141/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 24–31, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$737 ($105/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 24–29, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$577 ($115/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24, 2026 – Jan 4, 2027 (11 nights)
1 bed/1 bath, sleeps 4
$2,222 ($202/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 24–29, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,172 ($234/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–30, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,295 ($216/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,962 ($1,280/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–30, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,743 ($290/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–29, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,506 ($301/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,268 ($467/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 24–26, 2026 (2 nights)
Studio/1 bath, sleeps 4
$1,123 ($562/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,039 ($434/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24, 2026 – Jan 1, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,214 ($277/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24, 2026 – Jan 4, 2027 (11 nights)
2 bed/2 bath, sleeps 8
$3,170 ($288/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–28, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,268 ($317/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 24–30, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,524 ($254/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,717 ($245/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,167 ($595/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$4,603 ($658/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25–31, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,743 ($290/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,726 ($1,389/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25, 2026 – Jan 2, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$1,695 ($212/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,384 ($626/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25, 2026 – Jan 2, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,310 ($289/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,978 ($283/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,257 ($751/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,513 ($502/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

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Eagle's Nest Beach Resort

Marco Island, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$6,238 ($891/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,802 ($543/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,764 ($538/night)