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 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/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 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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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,795 ($685/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/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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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–18, 2026 (5 nights)
- 2 bed/3 bath, sleeps 8
- $4,711 ($942/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 Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,531 ($362/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
- $1,952 ($390/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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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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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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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 14–19, 2026 (5 nights)
- 1 bed/2 bath, sleeps 4
- $2,532 ($506/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 14–18, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $2,471 ($618/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,173 ($1,310/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 14–18, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($2,186/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 14–21, 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 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 15–22, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,077 ($440/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,298 ($471/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 15–22, 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 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,320 ($903/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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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 16–21, 2026 (5 nights)
- 2 bed/3 bath, sleeps 8
- $3,568 ($714/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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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 16–23, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,513 ($502/night)
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Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Dec 16–27, 2026 (11 nights)
- 2 bed/2 bath, sleeps 6
- $4,276 ($389/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 16–23, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 16–23, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,413 ($1,202/night)
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Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 16–23, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,660 ($237/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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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 17–27, 2026 (10 nights)
- 1 bed/2 bath, sleeps 4
- $7,928 ($793/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 17–23, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $4,112 ($685/night)
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The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,402 ($914/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,434 ($919/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,821 ($689/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($1,249/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 18–23, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $4,325 ($865/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,726 ($1,389/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,047 ($292/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,058 ($580/night)