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 Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,036 ($1,148/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,854 ($979/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,121 ($874/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $7,546 ($1,078/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,238 ($891/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,113 ($1,159/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,486 ($1,355/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,374 ($625/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,036 ($1,148/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,274 ($1,039/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,412 ($630/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,579 ($1,083/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,562 ($1,366/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,304 ($1,186/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,464 ($1,066/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $7,426 ($1,061/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,366 ($767/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,601 ($1,372/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $9,898 ($1,414/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–26, 2026 (6 nights)
- 1 bed/2 bath, sleeps 4
- $3,942 ($657/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,769 ($253/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–23, 2026 (3 nights)
- 2 bed/3 bath, sleeps 8
- $2,478 ($826/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,470 ($1,639/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–26, 2026 (6 nights)
- 1 bed/2 bath, sleeps 4
- $4,073 ($679/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,848 ($407/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 21–26, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $4,658 ($932/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 21–24, 2026 (3 nights)
- 1 bed/2 bath, sleeps 4
- $1,742 ($581/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 21–28, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,557 ($794/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 22–27, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($877/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 22–29, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,366 ($767/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 22–31, 2026 (9 nights)
- 2 bed/2 bath, sleeps 6
- $6,233 ($693/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 22–29, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,366 ($767/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 22–29, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $6,129 ($876/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,546 ($1,078/night)
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 23–30, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,944 ($1,278/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,410 ($1,201/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,748 ($821/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,892 ($985/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,443 ($635/night)