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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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 13–16, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,039 ($346/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 13–16, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,198 ($399/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 13–17, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,594 ($398/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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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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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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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 13–20, 2026 (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- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,276 ($611/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/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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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 13–17, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,383 ($346/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 13–19, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($440/night)
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The Point at Poipu
Koloa, Hawaii- Dec 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($440/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,350 ($907/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 14–19, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,952 ($390/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,440 ($740/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 14–19, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,249 ($450/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 15–23, 2026 (8 nights)
- 2 bed/2 bath, sleeps 6
- $3,199 ($400/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 16–23, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,760 ($394/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
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Lawai Beach Resort
Koloa, Hawaii- Dec 17–31, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($547/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 17–23, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,519 ($420/night)
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Club Wyndham Shearwater
Princeville, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
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The Cliffs at Princeville
Princeville, Hawaii- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 1 bed/2 bath, sleeps 8
- $7,655 ($547/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,968 ($424/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,674 ($953/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 18–23, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,179 ($436/night)
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The Cliffs at Princeville
Princeville, Hawaii- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 12
- $7,655 ($1,094/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,513 ($502/night)
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Lawai Beach Resort
Koloa, Hawaii- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $7,328 ($523/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,455 ($922/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,455 ($922/night)
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Hanalei Bay Resort
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
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Wyndham Kauai Coast Resort at the Beachboy
Kapaa, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (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 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
The Point at Poipu
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,832 ($547/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,086 ($727/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,455 ($922/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (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 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,275 ($611/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 19–24, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,952 ($390/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,094 ($728/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,238 ($891/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,184 ($455/night)