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- Jan 15–22, 2027 (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- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,611 ($802/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,238 ($891/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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The Point at Poipu
Koloa, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 23–30, 2027 (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- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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The Point at Poipu
Koloa, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,271 ($610/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Lawai Beach Resort
Koloa, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,749 ($393/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 30 – Feb 6, 2027 (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- Feb 5–12, 2027 (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- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 6–13, 2027 (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- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Feb 12–19, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,108 ($444/night)
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The Point at Poipu
Koloa, Hawaii- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,404 ($486/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,992 ($999/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,992 ($999/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (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- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,470 ($781/night)
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Lawai Beach Resort
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,821 ($689/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 14–21, 2027 (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- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,821 ($689/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,549 ($793/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 20–27, 2027 (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- Feb 25 – Mar 1, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $2,636 ($659/night)
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 26 – Mar 12, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $8,647 ($618/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 26 – Mar 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,821 ($689/night)