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 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,282 ($897/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,938 ($848/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,402 ($914/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,402 ($914/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,402 ($914/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 9–16, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,246 ($1,321/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 9–20, 2026 (11 nights)
- 2 bed/2 bath, sleeps 8
- $10,816 ($983/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 10–18, 2026 (8 nights)
- 3 bed/2 bath, sleeps 8
- $10,870 ($1,359/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
The Point at Poipu
Koloa, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,599 ($657/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,295 ($471/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,478 ($354/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($393/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,611 ($516/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 11–14, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $1,859 ($620/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,240 ($463/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,650 ($1,093/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (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- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,711 ($673/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,404 ($486/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,813 ($545/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,820 ($689/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 12–15, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $1,752 ($584/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,053 ($579/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,772 ($396/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,347 ($907/night)
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,456 ($922/night)
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The Cliffs at Princeville
Princeville, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,794 ($685/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,676 ($525/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,670 ($810/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,243 ($892/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,358 ($765/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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The Point at Poipu
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)