Winter Timeshare Rentals in Florida

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,330 ($266/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,222 ($603/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 21–31, 2026 (10 nights)
2 bed/2 bath, sleeps 8
$2,022 ($202/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 21–31, 2026 (10 nights)
1 bed/1 bath, sleeps 4
$950 ($95/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$2,750 ($550/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,436 ($287/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21, 2026 – Jan 1, 2027 (11 nights)
2 bed/2 bath, sleeps 8
$3,094 ($281/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 21–31, 2026 (10 nights)
1 bed/1 bath, sleeps 4
$1,304 ($130/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,057 ($211/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 21–24, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$247 ($82/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 21–24, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$535 ($178/night)

Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 21–26, 2026 (5 nights)
Studio/1 bath, sleeps 4
$6,560 ($1,312/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 21–24, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$487 ($162/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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Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 21–24, 2026 (3 nights)
1 bed/1 bath, sleeps 6
$929 ($310/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 21–25, 2026 (4 nights)
Studio/1 bath, sleeps 5
$2,685 ($671/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 21–29, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,205 ($276/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 21–31, 2026 (10 nights)
2 bed/2 bath, sleeps 8
$2,240 ($224/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 21–24, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$343 ($114/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 21–28, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,750 ($393/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,076 ($297/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$768 ($154/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,519 ($217/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21, 2026 – Jan 1, 2027 (11 nights)
1 bed/1 bath, sleeps 4
$1,664 ($151/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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Hilton Grand Vacations at SeaWorld

Orlando, Florida

Dec 21–28, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,696 ($385/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–28, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,107 ($158/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,682 ($240/night)

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Holiday Inn Club Vacations Orlando Breeze Resort

Davenport, Florida

Dec 22–29, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$6,020 ($860/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,488 ($213/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 22–27, 2026 (5 nights)
Studio/1 bath, sleeps 4
$7,105 ($1,421/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 22–29, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$968 ($138/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 22–29, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$719 ($103/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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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 22–26, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,054 ($264/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 22–30, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$999 ($125/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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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,505 ($358/night)

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 22–29, 2026 (7 nights)
3 bed/4 bath, sleeps 12
$13,105 ($1,872/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 22, 2026 – Jan 3, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$3,256 ($271/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–30, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,734 ($217/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
$3,295 ($824/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–30, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,362 ($295/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–30, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,268 ($159/night)

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Hilton Grand Vacations at Tuscany Village

Orlando, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,204 ($315/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22, 2026 – Jan 2, 2027 (11 nights)
2 bed/2 bath, sleeps 8
$3,230 ($294/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
$8,036 ($1,148/night)