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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Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 16–23, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,660 ($237/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 16–23, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,760 ($394/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 17–23, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $4,112 ($685/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 17–27, 2026 (10 nights)
- 1 bed/2 bath, sleeps 4
- $7,928 ($793/night)
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Lawai Beach Resort
Koloa, Hawaii- Dec 17–31, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($547/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,582 ($1,226/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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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,513 ($502/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $13,050 ($1,864/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
- $8,745 ($1,249/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,475 ($782/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (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- Dec 18–28, 2026 (10 nights)
- 1 bed/1 bath, sleeps 4
- $8,199 ($820/night)
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Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,932 ($276/night)
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The Cliffs at Princeville
Princeville, Hawaii- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 1 bed/2 bath, sleeps 8
- $7,655 ($547/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/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
- $9,617 ($1,374/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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/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
- $9,726 ($1,389/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
- $8,036 ($1,148/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,717 ($674/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,274 ($1,039/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,047 ($292/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 18–23, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $4,325 ($865/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,058 ($580/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,598 ($657/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
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,821 ($689/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
- $3,832 ($547/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/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
- $4,603 ($658/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,038 ($720/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,707 ($1,530/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,560 ($937/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,894 ($556/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,887 ($984/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,347 ($907/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
- $4,112 ($588/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
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Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $944 ($135/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,786 ($541/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,711 ($673/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,057 ($580/night)