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.
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 1–8, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $6,816 ($974/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 1–6, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,121 ($624/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 1–6, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($485/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,832 ($547/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,595 ($656/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 1–6, 2026 (5 nights)
- 1 bed/2 bath, sleeps 4
- $2,478 ($496/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 1–7, 2026 (6 nights)
- 3 bed/3 bath, sleeps 10
- $7,862 ($1,310/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 1–8, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,911 ($844/night)
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 1–8, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,742 ($249/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 1–6, 2026 (5 nights)
- 1 bed/2 bath, sleeps 4
- $2,478 ($496/night)
Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 2–9, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,512 ($216/night)
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,230 ($319/night)
Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Dec 2–7, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,654 ($331/night)
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,707 ($672/night)
Kahana Falls
Lahaina, Hawaii- Dec 3–10, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,096 ($299/night)
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 3–7, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $2,188 ($547/night)
WorldMark Kona Resort
Kailua-Kona, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
Pono Kai
Kapaa, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,769 ($253/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,619 ($374/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,649 ($521/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 4–9, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $1,632 ($326/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,794 ($685/night)
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 4–7, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $1,647 ($549/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Maui Beach Vacation Club
Kihei, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,650 ($236/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 4–7, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $832 ($278/night)
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,802 ($543/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,894 ($413/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,579 ($940/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,268 ($467/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
The Cliffs at Princeville
Princeville, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,742 ($249/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,473 ($782/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)