Winter Timeshare Rentals in Florida

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$10,216 ($1,460/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 27, 2026 – Jan 4, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$1,895 ($237/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,290 ($470/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,303 ($329/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$999 ($200/night)

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Disney's Animal Kingdom Villas - Jambo House

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$5,668 ($810/night)

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Marriott's Villas at Doral

Miami, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,222 ($603/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$866 ($144/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,527 ($1,218/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,096 ($299/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,161 ($309/night)

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Palm Beach Shores Resort and Vacation Villas

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,932 ($276/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,777 ($682/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,701 ($243/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,222 ($317/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$777 ($129/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$11,470 ($1,639/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,417 ($1,202/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

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Club Wyndham Santa Barbara

Pompano Beach, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,685 ($384/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,558 ($223/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Club Wyndham Sea Gardens

Pompano Beach, Florida

Dec 27, 2026 – Jan 2, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,439 ($240/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 27–31, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$781 ($195/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,378 ($276/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28–31, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$573 ($191/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$746 ($107/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$535 ($134/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28–31, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$586 ($195/night)

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Marriott Vacation Club Pulse, South Beach

Miami Beach, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
Studio/1 bath, sleeps 3
$2,750 ($550/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,581 ($226/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,734 ($248/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$995 ($142/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28–31, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$367 ($122/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$764 ($191/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 28–31, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$1,330 ($443/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$733 ($147/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$781 ($195/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$343 ($86/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
1 bed/1 bath, sleeps 4
$471 ($118/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,200 ($314/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 1, 2027 (4 nights)
2 bed/2 bath, sleeps 8
$995 ($249/night)

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Parc Soleil by Hilton Grand Vacations

Orlando, Florida

Dec 28, 2026 – Jan 3, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,660 ($277/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,956 ($280/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 28–31, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$271 ($90/night)