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 14–21, 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 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 15–19, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($769/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 15–22, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,384 ($626/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,508 ($501/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 15–25, 2027 (10 nights)
- 2 bed/2 bath, sleeps 6
- $6,347 ($635/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 17–25, 2027 (8 nights)
- 1 bed/2 bath, sleeps 4
- $4,380 ($547/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Feb 17–20, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,462 ($487/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Feb 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 17–23, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($767/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,650 ($1,093/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,649 ($521/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Feb 19 – Mar 5, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($469/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,649 ($521/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($315/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,053 ($579/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,592 ($656/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,061 ($437/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $11,906 ($1,701/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 19–27, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($821/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,821 ($689/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 19–26, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,617 ($517/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/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
- $7,328 ($1,047/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,469 ($496/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
- $4,930 ($704/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,451 ($493/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,108 ($1,444/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
- $6,560 ($937/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
- $3,001 ($429/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
- $6,015 ($859/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)
- Studio/1 bath, sleeps 4
- $3,513 ($502/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
- $5,470 ($781/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
- $3,949 ($564/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($424/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
- $6,565 ($938/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,892 ($985/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 20–26, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,850 ($475/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
- $3,731 ($533/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $14,195 ($2,028/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,565 ($938/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 20–26, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,504 ($584/night)