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
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,069 ($581/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Feb 6–13, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,271 ($610/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $2,917 ($417/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,560 ($937/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,516 ($1,502/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 6–13, 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 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,053 ($865/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 7–14, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,380 ($626/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 7–13, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,694 ($616/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,527 ($1,218/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 7–14, 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 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 7–14, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 7–14, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,366 ($767/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 7–14, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,276 ($611/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 7–14, 2027 (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- Feb 7–12, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,658 ($932/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 7–14, 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 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,015 ($859/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 7–14, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 7–14, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,649 ($521/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 8–14, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,538 ($756/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 8–13, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,478 ($496/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 9–14, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,350 ($670/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 10–14, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,554 ($638/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 11–18, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,892 ($985/night)
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The Point at Poipu
Koloa, Hawaii- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,404 ($486/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 12–19, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,069 ($438/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 12–19, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,213 ($459/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 12–19, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,200 ($1,171/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,274 ($1,039/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 12–19, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,884 ($983/night)