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 Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,658 ($665/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($412/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,756 ($965/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 30 – Feb 13, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $8,418 ($601/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 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- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,200 ($314/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 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 - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,358 ($765/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,901 ($700/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,420 ($489/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,412 ($630/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,039 ($720/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,284 ($469/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,298 ($471/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 2–14, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $7,546 ($629/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,470 ($781/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,175 ($739/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,148 ($735/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,746 ($821/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 5–12, 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 6–13, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,516 ($1,502/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
- $3,268 ($467/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)
- 1 bed/2 bath, sleeps 4
- $4,450 ($636/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
- $3,617 ($517/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,001 ($1,000/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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/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)
- 1 bed/2 bath, sleeps 4
- $3,405 ($486/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
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,298 ($614/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 Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
Verified & Protected
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)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/night)
Verified & Protected
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
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/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
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,560 ($937/night)