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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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,930 ($704/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,549 ($793/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,004 ($572/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,132 ($447/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,233 ($890/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,054 ($579/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,968 ($424/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,470 ($781/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 20–27, 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 North
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,404 ($486/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,350 ($478/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,527 ($361/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,898 ($1,557/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 20–27, 2027 (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 - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,592 ($656/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 21–28, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,494 ($642/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 21–28, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,328 ($761/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 21–28, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,649 ($521/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2027 (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- Feb 21–28, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $5,257 ($751/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Feb 21–25, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,418 ($604/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,412 ($630/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,511 ($787/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 21–26, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($986/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 22 – Mar 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 22–26, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,765 ($441/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 22–28, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($604/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 22–28, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,164 ($527/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 22 – Mar 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,505 ($501/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 23 – Mar 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 25 – Mar 1, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $2,636 ($659/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 26 – Mar 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 26 – Mar 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 26 – Mar 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 26 – Mar 5, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,617 ($517/night)