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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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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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,053 ($579/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 12–17, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $2,249 ($450/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,320 ($903/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,794 ($685/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 12–17, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,952 ($390/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 12–16, 2026 (4 nights)
- 2 bed/2 bath, sleeps 9
- $5,257 ($1,314/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 Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,399 ($486/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,202 ($743/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,121 ($874/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,428 ($347/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,054 ($436/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,801 ($829/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,712 ($673/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,993 ($856/night)
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Maui Schooner
Kihei, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,161 ($309/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,423 ($346/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 13–18, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,658 ($932/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,478 ($354/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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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–19, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,786 ($631/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/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 Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,595 ($656/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 13–18, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,450 ($490/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 Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,105 ($1,015/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
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 13–18, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,069 ($414/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,633 ($805/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 13–18, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $3,082 ($616/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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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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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,929 ($704/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
- $4,603 ($658/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 13–16, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,039 ($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
- $2,292 ($382/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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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 13–16, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,198 ($399/night)