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 Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,268 ($467/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
- $5,475 ($782/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 9–16, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $10,925 ($1,561/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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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,929 ($704/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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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,186 ($455/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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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,900 ($1,129/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/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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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)
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,427 ($204/night)
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WorldMark Park City
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 4 bed/4 bath, sleeps 10
- $3,687 ($527/night)
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Marriott Vacation Club at Los Sueños
Playa Jaco, Costa Rica- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 9–10, 2027 (1 night)
- Studio/1 bath, sleeps 4
- $551 ($551/night)
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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
- $3,268 ($467/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/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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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,831 ($404/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 9–13, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,327 ($582/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
- $6,565 ($938/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
- $6,565 ($938/night)
Royal Haciendas
Playa del Carmen, Mexico- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/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
- $3,568 ($510/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,365 ($766/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 9–12, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,251 ($417/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,294 ($471/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $10,380 ($1,483/night)
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Divi Dutch Village Beach Resort
Oranjestad, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,328 ($761/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
- $2,532 ($362/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/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
- $3,077 ($440/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
- $6,020 ($860/night)
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Villas at Disneyland Hotel
Anaheim, California- Jan 9–15, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,321 ($387/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
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/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
- $6,565 ($938/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)