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
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,674 ($953/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 13–20, 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- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Feb 13–20, 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- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,966 ($852/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 13–20, 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- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,474 ($782/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,222 ($603/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,202 ($743/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,928 ($1,132/night)
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Lawai Beach Resort
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,977 ($711/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,649 ($521/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,422 ($917/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,576 ($654/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,636 ($1,234/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 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
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,508 ($501/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,562 ($712/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,412 ($630/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,925 ($1,561/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,505 ($358/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 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- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,859 ($408/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,412 ($630/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,328 ($1,047/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,363 ($623/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,609 ($1,230/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,546 ($1,078/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,148 ($735/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,873 ($1,125/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,512 ($502/night)