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 Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 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 6–13, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $5,257 ($751/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,807 ($544/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,204 ($315/night)
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Paniolo Greens
Waikoloa Village, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,704 ($243/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 6–13, 2026 (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- Dec 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,448 ($493/night)
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Club Wyndham Mauna Loa Village
Kailua-Kona, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $2,276 ($325/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,336 ($619/night)
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Kahana Beach Resort
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,938 ($848/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,361 ($766/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,793 ($828/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,486 ($498/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,557 ($794/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,579 ($797/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–11, 2026 (5 nights)
- 3 bed/3 bath, sleeps 10
- $5,475 ($1,095/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,358 ($623/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,794 ($685/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
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Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 6–12, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($549/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,121 ($874/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,788 ($684/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,999 ($428/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,617 ($1,374/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,036 ($1,148/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 6–12, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($495/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 6–12, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($440/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,595 ($656/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,756 ($679/night)
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Hanalei Bay Resort
Princeville, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,205 ($315/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–11, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($833/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 7–20, 2026 (13 nights)
- 2 bed/2 bath, sleeps 6
- $6,173 ($475/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,938 ($848/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,282 ($897/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 7–10, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,198 ($399/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,257 ($751/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,494 ($642/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 9–15, 2026 (6 nights)
- 3 bed/3 bath, sleeps 8
- $5,748 ($958/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 9–19, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($820/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 9–19, 2026 (10 nights)
- Studio/1 bath, sleeps 2
- $2,941 ($294/night)