Winter Timeshare Rentals in Florida

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Jan 8–22, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$6,015 ($430/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–16, 2027 (8 nights)
3 bed/2 bath, sleeps 10
$2,436 ($305/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–15, 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 8–11, 2027 (3 nights)
2 bed/2 bath, sleeps 8
$973 ($324/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 8–15, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$559 ($80/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–13, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,566 ($313/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–14, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$986 ($164/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–11, 2027 (3 nights)
2 bed/2 bath, sleeps 6
$1,057 ($352/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–14, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,860 ($310/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–15, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,673 ($239/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–11, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$586 ($195/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–13, 2027 (5 nights)
2 bed/2 bath, sleeps 6
$1,550 ($310/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–14, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,475 ($246/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–13, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$1,276 ($255/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–15, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,039 ($291/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 8–11, 2027 (3 nights)
3 bed/2 bath, sleeps 10
$1,057 ($352/night)

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Eagle's Nest Beach Resort

Marco Island, Florida

Jan 8–15, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,513 ($502/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,242 ($177/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Jan 9–11, 2027 (2 nights)
Studio/1 bath, sleeps 5
$1,135 ($568/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,748 ($821/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Jan 9–16, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,831 ($404/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,179 ($740/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–12, 2027 (3 nights)
2 bed/2 bath, sleeps 6
$901 ($300/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–13, 2027 (4 nights)
3 bed/2 bath, sleeps 10
$1,150 ($287/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–13, 2027 (4 nights)
2 bed/2 bath, sleeps 6
$1,150 ($287/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–13, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$626 ($157/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–12, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$499 ($166/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–12, 2027 (3 nights)
3 bed/2 bath, sleeps 10
$901 ($300/night)

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Marriott's Villas at Doral

Miami, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,085 ($869/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,358 ($765/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,320 ($903/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 9–15, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$693 ($115/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 9–15, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$487 ($81/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–12, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$739 ($246/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 9–15, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,145 ($191/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Jan 9–15, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,172 ($195/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Jan 9–16, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,309 ($330/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–13, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$1,232 ($308/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–23, 2027 (14 nights)
3 bed/2 bath, sleeps 10
$4,054 ($290/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–23, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$3,321 ($237/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 9–16, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,581 ($226/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–23, 2027 (14 nights)
2 bed/2 bath, sleeps 6
$4,054 ($290/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 9–23, 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 9–13, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$940 ($235/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Jan 9–16, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,766 ($681/night)