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 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/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
- $7,545 ($1,078/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- Studio/1 bath, sleeps 2
- $2,150 ($358/night)
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The Cliffs at Princeville
Princeville, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,505 ($358/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $2,750 ($393/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,949 ($564/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $2,749 ($393/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,382 ($483/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,764 ($1,109/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($626/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/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
- $8,631 ($1,233/night)
Verified & Protected
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
- $6,020 ($860/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Lawai Beach Resort
Koloa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
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Hanalei Bay Resort
Princeville, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,901 ($700/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,769 ($824/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,930 ($704/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,112 ($588/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Pono Kai
Kapaa, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/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
- $4,069 ($581/night)
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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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The Point at Poipu
Koloa, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,330 ($619/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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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
- $7,655 ($1,094/night)
Verified & Protected
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
- $7,600 ($1,086/night)
Verified & Protected
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
- $7,109 ($1,016/night)
Verified & Protected
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
- $6,388 ($913/night)
Verified & Protected
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
- $5,442 ($777/night)
Verified & Protected
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
- $8,199 ($1,171/night)
Verified & Protected
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
- $6,020 ($860/night)
Verified & Protected
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)
Verified & Protected
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
- $8,091 ($1,156/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,821 ($689/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,404 ($486/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,456 ($922/night)
Verified & Protected
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
- $8,199 ($1,171/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $3,840 ($549/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,876 ($696/night)
Verified & Protected
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
- $6,091 ($870/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)
Verified & Protected
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
- $7,655 ($1,094/night)
Verified & Protected
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
- $6,129 ($876/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 27, 2026 – Jan 5, 2027 (9 nights)
- 2 bed/2 bath, sleeps 6
- $9,835 ($1,093/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $3,295 ($471/night)