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- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,800 ($829/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,330 ($619/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,602 ($657/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
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One Napili Way
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/2 bath, sleeps 6
- $2,423 ($346/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,658 ($665/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,206 ($601/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,859 ($408/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,205 ($315/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,793 ($828/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,987 ($284/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Carlsbad Inn Beach Resort
Carlsbad, California- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,537 ($648/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,513 ($502/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–14, 2026 (9 nights)
- 2 bed/2 bath, sleeps 8
- $7,088 ($788/night)
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Pueblo Bonito Rose Spa & Resort
Cabo San Lucas, Mexico- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,220 ($174/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,222 ($460/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $4,930 ($704/night)
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Blue Tree Resort at Lake Buena Vista
Orlando, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $760 ($109/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 10
- $2,745 ($392/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,938 ($563/night)
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Lifestyle Holidays Vacation Resort - Puerto Plata
Puerto Plata, Dominican Republic- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $832 ($119/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,374 ($625/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $11,466 ($1,638/night)
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Grand Beach Resort
Orlando, Florida- Dec 5–12, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $1,660 ($237/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
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Lighthouse Resort & Club
Sanibel Island, Florida- Dec 5–12, 2026 (7 nights)
- 3 bed/2 bath, sleeps 6
- $2,750 ($393/night)
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Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,856 ($265/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,475 ($782/night)
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Marriott's Phuket Beach Club
Phuket, Thailand- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
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Playa Grande Resort & Grand Spa
Cabo San Lucas, Mexico- Dec 5–12, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,077 ($440/night)