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 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($393/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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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,211 ($602/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)
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,832 ($547/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
- $3,382 ($483/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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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,478 ($354/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/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
- $5,938 ($848/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
- $5,366 ($767/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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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)
- Studio/1 bath, sleeps 4
- $4,053 ($579/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 Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/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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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
- $6,510 ($930/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
- $4,112 ($588/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
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)
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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
- $3,350 ($478/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,320 ($903/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
- $3,568 ($510/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
- $4,494 ($642/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
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,995 ($428/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
- $3,486 ($498/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–16, 2026 (4 nights)
- 1 bed/2 bath, sleeps 4
- $1,769 ($442/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)
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,835 ($548/night)
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The Point at Poipu
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/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
- $4,930 ($704/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
- $6,565 ($938/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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Marriott's Kauai Beach Club
Lihue, 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
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,579 ($797/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
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,240 ($463/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
- $4,876 ($696/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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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
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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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
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)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,502 ($1,072/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,202 ($743/night)