Winter Timeshare Rentals in Florida

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Hyatt Windward Pointe Resort

Key West, Florida

Dec 20–24, 2026 (4 nights)
2 bed/2 bath, sleeps 6
$1,878 ($470/night)

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Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
Studio/1 bath, sleeps 4
$2,536 ($423/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–27, 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 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$5,312 ($759/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,617 ($1,374/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,564 ($938/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,420 ($774/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,020 ($860/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
3 bed/2 bath, sleeps 10
$2,153 ($359/night)

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Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,858 ($408/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,892 ($985/night)

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Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
Studio/1 bath, sleeps 4
$2,955 ($492/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,712 ($673/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
Studio/1 bath, sleeps 5
$3,850 ($642/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 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 21–24, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$535 ($178/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–24, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$959 ($320/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–24, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$719 ($240/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–24, 2026 (3 nights)
2 bed/2 bath, sleeps 6
$959 ($320/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,458 ($208/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,664 ($238/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–24, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$719 ($240/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 21–28, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$959 ($137/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–29, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,214 ($277/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,605 ($321/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,230 ($461/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,924 ($418/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–30, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,647 ($206/night)

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 22–26, 2026 (4 nights)
Studio/1 bath, sleeps 4
$3,077 ($769/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,091 ($1,156/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)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 22–29, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$10,699 ($1,528/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–26, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$826 ($206/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,110 ($1,016/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,200 ($1,171/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–30, 2026 (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 22–25, 2026 (3 nights)
2 bed/2 bath, sleeps 6
$959 ($320/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–25, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$271 ($90/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
$535 ($178/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–25, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$719 ($240/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–25, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$959 ($320/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–26, 2026 (4 nights)
2 bed/2 bath, sleeps 6
$1,524 ($381/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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–25, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$415 ($138/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–26, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$1,524 ($381/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

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