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 North
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,676 ($525/night)
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The Point at Poipu
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,478 ($354/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,240 ($463/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,358 ($765/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (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- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,820 ($689/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,112 ($588/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,650 ($1,093/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (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- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,820 ($689/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,565 ($652/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (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- Dec 13–18, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($768/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,478 ($354/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 13–18, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $3,082 ($616/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,748 ($535/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,213 ($745/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,595 ($656/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,929 ($704/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $2,968 ($424/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 14–24, 2026 (10 nights)
- 2 bed/3 bath, sleeps 8
- $12,000 ($1,200/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,865 ($811/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 15–22, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,556 ($937/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 15–22, 2026 (7 nights)
- 1 bed/1 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- Dec 15–22, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Dec 16–27, 2026 (11 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($488/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 16–21, 2026 (5 nights)
- 2 bed/3 bath, sleeps 8
- $4,112 ($822/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 16–23, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,513 ($502/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 17–24, 2026 (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- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,470 ($781/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,295 ($471/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 18–24, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($604/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,181 ($1,312/night)
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Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,099 ($157/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,418 ($1,203/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,099 ($728/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,272 ($1,039/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,838 ($977/night)