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 Ko Olina Beach Club
Kapolei, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,265 ($895/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,692 ($813/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,522 ($1,217/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,712 ($673/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,358 ($765/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,304 ($1,186/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 20–26, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $5,420 ($903/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,184 ($883/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,199 ($1,171/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,292 ($899/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,312 ($759/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 20–26, 2026 (6 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($458/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,669 ($953/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,617 ($1,088/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,802 ($543/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 21–26, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,276 ($855/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,437 ($1,062/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 22–26, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $4,630 ($1,158/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,380 ($1,483/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 22–29, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,731 ($533/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 22–26, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($1,096/night)
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 22–24, 2026 (2 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($830/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 22–31, 2026 (9 nights)
- 2 bed/2 bath, sleeps 6
- $6,342 ($705/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 22–29, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,510 ($930/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,854 ($979/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,982 ($1,140/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 22, 2026 – Jan 1, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $11,742 ($1,174/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 23–27, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $3,600 ($900/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 23, 2026 – Jan 2, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $12,832 ($1,283/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 23–26, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($1,153/night)
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Pono Kai
Kapaa, Hawaii- Dec 23–30, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
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Pono Kai
Kapaa, Hawaii- Dec 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 23, 2026 – Jan 2, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $10,469 ($1,047/night)
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Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 23, 2026 – Jan 1, 2027 (9 nights)
- 1 bed/1 bath, sleeps 6
- $4,832 ($537/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,764 ($1,109/night)
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Hanalei Bay Resort
Princeville, Hawaii- Dec 24–31, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,696 ($385/night)