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.
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,344 ($478/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,031 ($576/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,516 ($1,502/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,219 ($1,031/night)
Papakea Resort
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,984 ($712/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,031 ($576/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–15, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($386/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($412/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,083 ($1,012/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,783 ($398/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,318 ($1,474/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,472 ($925/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,717 ($674/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,129 ($876/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,274 ($1,039/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,412 ($630/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,382 ($483/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 12–19, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 12–16, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,765 ($441/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 12–17, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($724/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 13–20, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,268 ($467/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,412 ($630/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Kahana Falls
Lahaina, Hawaii- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,085 ($298/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,382 ($483/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,107 ($587/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,516 ($1,502/night)
Kahana Villa Resort
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,276 ($325/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,077 ($440/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 16–26, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($820/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,318 ($1,474/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,298 ($471/night)