Winter Timeshare Rentals in Florida

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Sheraton Vistana Villages

Orlando, Florida

Dec 19–24, 2026 (5 nights)
2 bed/2 bath, sleeps 6
$1,110 ($222/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 19, 2026 – Jan 2, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$1,343 ($96/night)

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Parc Soleil by Hilton Grand Vacations

Orlando, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,205 ($315/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
$6,129 ($876/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–22, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$648 ($216/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 19–26, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$10,346 ($1,478/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)

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
$8,636 ($1,234/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$693 ($99/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
$8,636 ($1,234/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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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,657 ($731/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–28, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$3,213 ($357/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
$8,200 ($1,171/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$6,565 ($938/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 19, 2026 – Jan 2, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$1,834 ($131/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
2 bed/2 bath, sleeps 9
$6,020 ($1,204/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–22, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$1,207 ($402/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19, 2026 – Jan 2, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$3,875 ($277/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,295 ($471/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
$7,731 ($1,104/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 19, 2026 – Jan 1, 2027 (13 nights)
1 bed/1 bath, sleeps 4
$1,264 ($97/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
$5,693 ($813/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–31, 2026 (12 nights)
2 bed/2 bath, sleeps 8
$3,308 ($276/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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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,629 ($233/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)
3 bed/2 bath, sleeps 10
$1,524 ($381/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,352 ($270/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$941 ($134/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,894 ($556/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
$2,423 ($346/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,260 ($323/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,240 ($463/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
$4,983 ($712/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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The Villas at Disney's Grand Floridian Resort & Spa

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 5
$2,576 ($515/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
$2,423 ($346/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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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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,003 ($201/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,077 ($440/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–22, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$875 ($292/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,352 ($270/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–28, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,935 ($215/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–28, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$2,602 ($289/night)