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- 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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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
- $5,366 ($767/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Feb 23 – Mar 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/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
- $2,532 ($633/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Feb 25 – Mar 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,510 ($502/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 26 – Mar 5, 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 26 – Mar 5, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,222 ($603/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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Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 26 – Mar 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,886 ($412/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)
- 1 bed/1 bath, sleeps 4
- $4,527 ($647/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)
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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
- $3,458 ($494/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 26 – Mar 5, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,467 ($352/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 26 – Mar 5, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,132 ($447/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 26 – Mar 2, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,249 ($562/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
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 26 – Mar 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,954 ($565/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 26 – Mar 2, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,471 ($618/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
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 26 – Mar 12, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $8,647 ($618/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
- $3,069 ($438/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
- $4,847 ($692/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 26 – Mar 5, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,981 ($1,140/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,459 ($351/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,238 ($891/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,733 ($533/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,944 ($1,421/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,001 ($429/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,112 ($588/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $13,650 ($1,950/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,560 ($937/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,625 ($661/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,344 ($478/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,358 ($765/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,840 ($406/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,733 ($533/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,679 ($668/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,963 ($423/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,619 ($374/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)