Winter Timeshare Rentals in Florida

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–28, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,295 ($216/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–25, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$719 ($240/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23, 2026 – Jan 1, 2027 (9 nights)
2 bed/2 bath, sleeps 8
$2,449 ($272/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23, 2026 – Jan 1, 2027 (9 nights)
1 bed/1 bath, sleeps 4
$1,821 ($202/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Dec 23–28, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$3,181 ($636/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–30, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 23–27, 2026 (4 nights)
Studio/1 bath, sleeps 5
$2,313 ($578/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 23–28, 2026 (5 nights)
Studio/1 bath, sleeps 5
$4,063 ($813/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,978 ($283/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 23–28, 2026 (5 nights)
Studio/1 bath, sleeps 5
$4,063 ($813/night)

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WorldMark Orlando – Reunion

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$2,641 ($377/night)

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The Villas at Disney's Grand Floridian Resort & Spa

Lake Buena Vista, Florida

Dec 23–29, 2026 (6 nights)
Studio/1 bath, sleeps 5
$5,558 ($926/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–28, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,312 ($262/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–28, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$946 ($189/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–28, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$679 ($136/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$8,740 ($1,249/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–27, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,268 ($317/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–27, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$1,769 ($442/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–27, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,268 ($317/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–27, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$941 ($235/night)

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Hyatt Sunset Harbor Resort

Key West, Florida

Dec 24–27, 2026 (3 nights)
2 bed/2.5 bath, sleeps 6
$3,949 ($1,316/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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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)

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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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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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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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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24, 2026 – Jan 2, 2027 (9 nights)
1 bed/1 bath, sleeps 4
$1,869 ($208/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24, 2026 – Jan 2, 2027 (9 nights)
2 bed/2 bath, sleeps 8
$2,545 ($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)

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Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/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)
2 bed/2 bath, sleeps 8
$5,802 ($829/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
$5,693 ($813/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)
2 bed/2 bath, sleeps 8
$4,930 ($704/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
$3,622 ($517/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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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)

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)

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)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,096 ($299/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,096 ($299/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
$5,693 ($813/night)