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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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26, 2026 – Jan 3, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $2,440 ($305/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 26–28, 2026 (2 nights)
- Studio/1 bath, sleeps 5
- $1,495 ($748/night)
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Holiday Inn Club Vacations Cape Canaveral Beach Resort
Cape Canaveral, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 10
- $1,856 ($265/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,061 ($294/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $4,222 ($603/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,185 ($455/night)
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Sheraton Vistana Villages
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,542 ($220/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26–31, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,436 ($287/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,982 ($283/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($237/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $737 ($105/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
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Marriott's Royal Palms
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
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Vistana Beach Club
Jensen Beach, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/night)
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Westgate Lakes Resort & Spa
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,442 ($206/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 4 bed/4 bath, sleeps 12
- $6,434 ($919/night)
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The Galleon Resort
Key West, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,458 ($494/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $901 ($150/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,096 ($299/night)
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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
- $5,910 ($844/night)
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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
- $5,147 ($735/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 27–31, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $764 ($191/night)
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WorldMark Palm Aire
Pompano Beach, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,549 ($221/night)
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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
- $8,723 ($1,246/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($248/night)
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CHOOSE YOUR OWN DATES
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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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,688 ($670/night)
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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
- $6,892 ($985/night)
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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
- $9,181 ($1,312/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,688 ($670/night)
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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
- $9,181 ($1,312/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/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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CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $976 ($139/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $5,440 ($777/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,743 ($549/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $13,105 ($1,872/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,632 ($326/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)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $4,930 ($704/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,688 ($670/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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CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 27–31, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $471 ($118/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)