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 Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,595 ($656/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,775 ($825/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
The Point at Poipu
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,832 ($547/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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The Point at Poipu
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,966 ($852/night)
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The Point at Poipu
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,709 ($816/night)
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The Point at Poipu
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,924 ($418/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,873 ($1,125/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,671 ($810/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,001 ($1,000/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,121 ($874/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 20–26, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($549/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($550/night)
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The Point at Poipu
Koloa, Hawaii- Dec 22, 2026 – Jan 1, 2027 (10 nights)
- 2 bed/2 bath, sleeps 6
- $6,456 ($646/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 23, 2026 – Jan 1, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $8,717 ($969/night)
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Lawai Beach Resort
Koloa, Hawaii- Dec 24–31, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,404 ($486/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,884 ($983/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,984 ($855/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,067 ($1,295/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,291 ($1,042/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,545 ($1,078/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,445 ($921/night)
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The Point at Poipu
Koloa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)