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 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,527 ($1,218/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 27, 2026 – Jan 1, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($877/night)
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The Point at Poipu
Koloa, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $7,764 ($1,294/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 29, 2026 – Jan 2, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $1,856 ($464/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 30, 2026 – Jan 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,981 ($1,140/night)
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The Point at Poipu
Koloa, Hawaii- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Club Wyndham Shearwater
Princeville, Hawaii- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,072 ($439/night)
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Hanalei Bay Resort
Princeville, Hawaii- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,696 ($385/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,873 ($1,125/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,072 ($439/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,893 ($699/night)
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The Point at Poipu
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,001 ($429/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,306 ($329/night)
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WorldMark Kapaa Shore
Kapaa, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,543 ($363/night)
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The Point at Poipu
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,599 ($657/night)
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The Point at Poipu
Koloa, Hawaii- Jan 2–8, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($731/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2027 (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- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,099 ($728/night)
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The Cliffs at Princeville
Princeville, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,268 ($467/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2027 (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- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,938 ($848/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 8–14, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,519 ($420/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 8–14, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,903 ($484/night)
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The Cliffs at Princeville
Princeville, Hawaii- Jan 8–15, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,660 ($237/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 9–16, 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- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 11–14, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,198 ($399/night)