Winter Timeshare Rentals in Florida

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 1–3, 2026 (2 nights)
Studio/1 bath, sleeps 5
$1,277 ($639/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 1–8, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,458 ($494/night)

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Disney's Animal Kingdom Villas - Jambo House

Lake Buena Vista, Florida

Dec 1–5, 2026 (4 nights)
1 bed/1 bath, sleeps 5
$7,010 ($1,752/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 1–6, 2026 (5 nights)
3 bed/3 bath, sleeps 10
$2,750 ($550/night)

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Disney's Riviera Resort

Lake Buena Vista, Florida

Dec 1–2, 2026 (1 night)
Studio/1 bath, sleeps 5
$622 ($622/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 1–8, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,874 ($839/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 1–9, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$3,840 ($480/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 2–9, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$995 ($142/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 2–6, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$648 ($162/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 3–6, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$2,423 ($808/night)

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Marriott's Villas at Doral

Miami, Florida

Dec 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,382 ($626/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$995 ($142/night)

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Westgate Town Center

Kissimmee, Florida

Dec 4–11, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,022 ($432/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,696 ($385/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,914 ($416/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 4–11, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,404 ($486/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 4–7, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$535 ($178/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,603 ($658/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,750 ($393/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,206 ($601/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,968 ($424/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,618 ($374/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 5–9, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,330 ($332/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$995 ($142/night)

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Grand Beach Resort

Orlando, Florida

Dec 5–12, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$1,660 ($237/night)

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Shell Island Beach Club

Sanibel Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,750 ($393/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,404 ($486/night)

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Blue Tree Resort at Lake Buena Vista

Orlando, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$760 ($109/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,603 ($658/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,600 ($514/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,222 ($603/night)

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Lighthouse Resort & Club

Sanibel Island, Florida

Dec 5–12, 2026 (7 nights)
3 bed/2 bath, sleeps 6
$2,750 ($393/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,458 ($494/night)

Westgate Lakes Resort & Spa

Orlando, Florida

Dec 6–13, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$777 ($111/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 6–11, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,605 ($321/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,330 ($190/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–10, 2026 (4 nights)
3 bed/3 bath, sleeps 10
$1,550 ($388/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–12, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$786 ($131/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–17, 2026 (11 nights)
2 bed/2 bath, sleeps 8
$1,996 ($181/night)

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Vacation Village at Parkway

Kissimmee, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,385 ($198/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–11, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$2,531 ($506/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–17, 2026 (11 nights)
2 bed/2 bath, sleeps 8
$2,310 ($210/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,290 ($470/night)

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Hilton Grand Vacations at SeaWorld

Orlando, Florida

Dec 6–13, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$2,478 ($354/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,457 ($494/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,568 ($510/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,990 ($427/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–17, 2026 (11 nights)
1 bed/1 bath, sleeps 4
$968 ($88/night)