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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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,976 ($854/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $2,696 ($385/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
- $4,821 ($689/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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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,204 ($315/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)
Verified & Protected
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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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/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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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $3,077 ($440/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($768/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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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 15–22, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,384 ($626/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 17–25, 2027 (8 nights)
- 1 bed/2 bath, sleeps 4
- $4,380 ($547/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)
Verified & Protected
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)
Verified & Protected
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)
Verified & Protected
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)
Verified & Protected
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)
Verified & Protected
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)
Verified & Protected
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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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Feb 21–25, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,418 ($604/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 22 – Mar 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,505 ($501/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Feb 23 – Mar 2, 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- Feb 25 – Mar 1, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $2,636 ($659/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Feb 25 – Mar 2, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,510 ($502/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 26 – Mar 5, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,467 ($352/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)
Verified & Protected
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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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,840 ($406/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)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 28 – Mar 4, 2027 (4 nights)
- 1 bed/2 bath, sleeps 4
- $1,987 ($497/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)