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
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,764 ($538/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Feb 28 – Mar 4, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,594 ($398/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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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 18–25, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,836 ($548/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 18–25, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $21,825 ($3,118/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 25, 2027 – Jan 1, 2028 (7 nights)
- Studio/1 bath, sleeps 4
- $6,565 ($938/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/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)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,546 ($1,078/night)
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Maui Schooner
Kihei, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/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)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 31, 2027 – Jan 7, 2028 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)