Winter Timeshare Rentals
Winter getaways are always popular, making now the perfect time to secure exclusive timeshare deals for your seasonal escape! Whether you're dreaming of a snowy mountain retreat or a warm-weather getaway, these timeshare rentals offer the perfect setting to make your winter vacation unforgettable.
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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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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 5
- $1,932 ($276/night)
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Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,563 ($938/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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Marriott's Grande Vista
Orlando, Florida- Dec 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($440/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $950 ($136/night)
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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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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/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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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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Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,527 ($647/night)
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Club Wyndham Royal Vista
Pompano Beach, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 9
- $6,782 ($969/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/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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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/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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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 21–24, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $535 ($178/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 Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–27, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,743 ($290/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 21–24, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $343 ($114/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–27, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,743 ($290/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,924 ($418/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 Ocean Walk
Daytona Beach, Florida- Dec 21–31, 2026 (10 nights)
- 1 bed/1 bath, sleeps 4
- $950 ($95/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–26, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–26, 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 21–31, 2026 (10 nights)
- 1 bed/1 bath, sleeps 4
- $1,304 ($130/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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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,821 ($689/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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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 Cypress Palms
Kissimmee, Florida- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,057 ($211/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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 21–27, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,295 ($216/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 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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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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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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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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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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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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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 22–26, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,114 ($279/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 22, 2026 – Jan 2, 2027 (11 nights)
- 1 bed/1 bath, sleeps 4
- $1,730 ($157/night)