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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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 9–15, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,150 ($358/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,031 ($576/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,611 ($1,087/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,772 ($396/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $808 ($115/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,252 ($750/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–13, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $940 ($235/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–13, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,150 ($287/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,622 ($517/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,309 ($330/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $11,470 ($1,639/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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The Cliff Club at Snowbird
Snowbird, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/3 bath, sleeps 10
- $10,924 ($1,561/night)
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Royal Haciendas
Playa del Carmen, Mexico- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
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Sunrise Lodge by Hilton Grand Vacations
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,494 ($642/night)
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Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,866 ($267/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $9,290 ($1,327/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,358 ($765/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,920 ($1,560/night)
Royal Haciendas
Playa del Carmen, Mexico- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,455 ($922/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,731 ($533/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 9–16, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $2,279 ($326/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,179 ($740/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($393/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,192 ($313/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $7,655 ($1,094/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Royal Haciendas
Playa del Carmen, Mexico- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $1,110 ($159/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,474 ($782/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–16, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $6,510 ($1,085/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–16, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $6,892 ($1,149/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–15, 2027 (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- Jan 10–15, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,242 ($248/night)