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
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $11,661 ($1,666/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,214 ($602/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,565 ($652/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $12,614 ($1,802/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $5,290 ($756/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,472 ($925/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,761 ($1,252/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,963 ($423/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,252 ($750/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,625 ($661/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,560 ($937/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,655 ($1,094/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,268 ($467/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,459 ($351/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,181 ($1,312/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($626/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,503 ($929/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,359 ($480/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,832 ($547/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($412/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 18–25, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,938 ($848/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 24–31, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $16,918 ($2,417/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 24–31, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,510 ($930/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,006 ($1,001/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 31, 2027 – Jan 7, 2028 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 31, 2027 – Jan 7, 2028 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,470 ($1,639/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 31, 2027 – Jan 7, 2028 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 31, 2027 – Jan 7, 2028 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,562 ($1,366/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 8–15, 2028 (7 nights)
- 3 bed/3 bath, sleeps 10
- $11,470 ($1,639/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 18–25, 2028 (7 nights)
- 3 bed/2 bath, sleeps 8
- $10,921 ($1,560/night)