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- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,859 ($408/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,532 ($362/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (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- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,854 ($1,265/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,112 ($588/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,552 ($936/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,166 ($595/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $4,271 ($610/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 16–17, 2027 (1 night)
- Studio/1 bath, sleeps 4
- $543 ($543/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 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- Jan 17–24, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,200 ($1,171/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,859 ($408/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 18–22, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($769/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 20–24, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,100 ($525/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Jan 22–29, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,489 ($641/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,859 ($408/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 26 – Feb 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 30 – Feb 6, 2027 (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- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($611/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)