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 1–8, 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 3–12, 2026 (9 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($911/night)
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Pono Kai
Kapaa, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,769 ($253/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Makai Club Resort
Princeville, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,749 ($393/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 5–9, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,612 ($403/night)
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Pono Kai
Kapaa, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 5–9, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,856 ($464/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,602 ($657/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $3,840 ($549/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 5–12, 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 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,807 ($544/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,361 ($766/night)
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Hanalei Bay Resort
Princeville, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,205 ($315/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 8–12, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,612 ($403/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 8–12, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,856 ($464/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 9–15, 2026 (6 nights)
- 3 bed/3 bath, sleeps 8
- $5,748 ($958/night)
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The Cliffs at Princeville
Princeville, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $4,031 ($576/night)
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Pono Kai
Kapaa, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,769 ($253/night)
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Pono Kai
Kapaa, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,772 ($253/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,110 ($1,016/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,750 ($393/night)
The Point at Poipu
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,876 ($696/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,602 ($657/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,494 ($642/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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The Point at Poipu
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
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The Point at Poipu
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–16, 2026 (4 nights)
- 1 bed/2 bath, sleeps 4
- $1,769 ($442/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,110 ($1,016/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,294 ($471/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,276 ($611/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $2,968 ($424/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Hanalei Bay Resort
Princeville, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,314 ($331/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,276 ($611/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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The Point at Poipu
Koloa, Hawaii- Dec 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($549/night)