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- Jan 22–29, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,380 ($626/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 22–29, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,023 ($718/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,535 ($362/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,611 ($516/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,276 ($325/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,222 ($603/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,129 ($876/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,291 ($470/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,914 ($416/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($412/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,916 ($559/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,191 ($456/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,892 ($985/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,442 ($777/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,733 ($533/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($455/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,001 ($1,000/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,475 ($782/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,276 ($611/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 24–31, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 27 – Feb 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,938 ($848/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 27 – Feb 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,914 ($416/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 29 – Feb 7, 2027 (9 nights)
- Studio/1 bath, sleeps 4
- $3,115 ($346/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,365 ($1,195/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 29 – Feb 12, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $6,510 ($465/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,510 ($930/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,023 ($718/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 29 – Feb 7, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $5,470 ($608/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Kahana Falls
Lahaina, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,550 ($221/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 30 – Feb 13, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $8,418 ($601/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,039 ($434/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,658 ($665/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,069 ($438/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,274 ($1,039/night)