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.
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,745 ($1,249/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,984 ($712/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,177 ($1,311/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,069 ($438/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,123 ($303/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
One Napili Way
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/2 bath, sleeps 6
- $1,932 ($276/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,358 ($765/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,687 ($670/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,603 ($658/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,214 ($602/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 6–17, 2026 (11 nights)
- 1 bed/1 bath, sleeps 4
- $6,919 ($629/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,450 ($636/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,741 ($392/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $3,840 ($549/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
Kahana Beach Resort
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,061 ($580/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,062 ($437/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,999 ($428/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 8–11, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $2,150 ($717/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 8–12, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($769/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 9–13, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $1,769 ($442/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 9–16, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $7,045 ($1,006/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,726 ($532/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,718 ($531/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 11–16, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $1,550 ($310/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,535 ($505/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,611 ($516/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 11–18, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)