Winter Timeshare Rentals in Florida

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,886 ($412/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–23, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$499 ($166/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/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)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20, 2026 – Jan 1, 2027 (12 nights)
1 bed/1 bath, sleeps 4
$2,345 ($195/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,590 ($265/night)

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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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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 20, 2026 – Jan 3, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$1,260 ($90/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,222 ($603/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,968 ($424/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,590 ($265/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–23, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$719 ($240/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
$6,455 ($922/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)

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
$8,526 ($1,218/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 20–25, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$799 ($160/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–27, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,750 ($393/night)

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Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,020 ($860/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
$6,884 ($983/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 20–25, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$535 ($107/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 20–25, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$888 ($178/night)

Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,978 ($283/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)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–24, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$1,277 ($319/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,384 ($626/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20, 2026 – Jan 2, 2027 (13 nights)
2 bed/2 bath, sleeps 8
$3,487 ($268/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)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20, 2026 – Jan 2, 2027 (13 nights)
1 bed/1 bath, sleeps 4
$2,567 ($197/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–24, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$959 ($240/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
$7,110 ($1,016/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,513 ($502/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–24, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$959 ($240/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)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,022 ($432/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20, 2026 – Jan 3, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,818 ($273/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$2,586 ($370/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 20–26, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$3,295 ($549/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–23, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$535 ($178/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,042 ($292/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
$2,750 ($393/night)

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Marriott's Imperial Palm Villas

Orlando, Florida

Dec 20–27, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$1,660 ($237/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,586 ($370/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,894 ($271/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 20, 2026 – Jan 3, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$2,741 ($196/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–26, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$3,948 ($658/night)