Winter Timeshare Rentals in Florida

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 9–16, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 9–16, 2026 (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

Dec 9–12, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$684 ($228/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 9–12, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$451 ($150/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 9–13, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$648 ($162/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 9–13, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$511 ($128/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 9–13, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$995 ($249/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 10–14, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$995 ($249/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 10–14, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$511 ($128/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,306 ($472/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 10–13, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$535 ($178/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 10–13, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$439 ($146/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 10–13, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$808 ($269/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 10–14, 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 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,622 ($517/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 11–13, 2026 (2 nights)
Studio/1 bath, sleeps 5
$981 ($491/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,077 ($615/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$764 ($153/night)

DiamondHead Beach Resort

Fort Myers Beach, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,768 ($253/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–18, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$1,550 ($221/night)

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Eagle's Nest Beach Resort

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,813 ($545/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–19, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,387 ($173/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–15, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$511 ($128/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–16, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$946 ($189/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–19, 2026 (8 nights)
3 bed/2 bath, sleeps 10
$2,109 ($264/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 11–17, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$2,423 ($404/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–14, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$424 ($141/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–16, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$679 ($136/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,077 ($615/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–18, 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 11–15, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$648 ($162/night)

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Boulder Ridge Villas at Disney's Wilderness Lodge

Lake Buena Vista, Florida

Dec 11–17, 2026 (6 nights)
Studio/1 bath, sleeps 5
$5,473 ($912/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–14, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$808 ($269/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–14, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$535 ($178/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–20, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,330 ($148/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,314 ($331/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–20, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$1,778 ($198/night)

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DiamondHead Beach Resort

Fort Myers Beach, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,123 ($303/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,949 ($564/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–14, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$439 ($146/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–15, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$995 ($249/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–20, 2026 (9 nights)
3 bed/2 bath, sleeps 10
$2,667 ($296/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$746 ($107/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–19, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,039 ($130/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$1,180 ($236/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–16, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,312 ($262/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,295 ($471/night)