Winter Timeshare Rentals in Florida

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The Galleon Resort

Key West, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,840 ($549/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,136 ($162/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 19–23, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$897 ($224/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,658 ($665/night)

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 19–23, 2026 (4 nights)
Studio/1 bath, sleeps 4
$3,670 ($917/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,274 ($1,039/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,666 ($524/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 19–23, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$764 ($191/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,840 ($549/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 19–27, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$7,437 ($930/night)

Westgate Town Center

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,818 ($260/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,603 ($658/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,150 ($307/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 19–23, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$523 ($131/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,274 ($1,039/night)

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Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,634 ($376/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,265 ($895/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 5
$4,191 ($838/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,910 ($844/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–23, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$826 ($206/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,930 ($704/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Marriott's Imperial Palm Villas

Orlando, Florida

Dec 19–26, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$3,294 ($471/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–23, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,114 ($279/night)

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Parc Soleil by Hilton Grand Vacations

Orlando, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,453 ($779/night)

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Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,967 ($424/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–22, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$507 ($169/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$3,513 ($502/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–22, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$941 ($314/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,981 ($426/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 4
$2,123 ($425/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,968 ($424/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,265 ($895/night)

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Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,878 ($268/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)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,647 ($235/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20, 2026 – Jan 1, 2027 (12 nights)
1 bed/1 bath, sleeps 4
$1,795 ($150/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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–26, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,682 ($280/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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Hyatt Sunset Harbor Resort

Key West, Florida

Dec 20–27, 2026 (7 nights)
Studio/1 bath, sleeps 2
$2,641 ($377/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
$710 ($178/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
$4,565 ($652/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
$2,276 ($325/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)