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 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 30 – Feb 7, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($575/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)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,740 ($820/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 31 – Feb 7, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,458 ($494/night)
Maui Banyan Vacation Club
Kihei, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,200 ($314/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,976 ($854/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,284 ($469/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,121 ($874/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,649 ($521/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 2–14, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $6,107 ($509/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 4–14, 2027 (10 nights)
- 2 bed/2 bath, sleeps 6
- $9,072 ($907/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,175 ($739/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,148 ($735/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,390 ($341/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $8,990 ($1,284/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,470 ($781/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,191 ($456/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($767/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,023 ($718/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,944 ($1,421/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,271 ($610/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,320 ($903/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,045 ($864/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($424/night)
Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,840 ($406/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,535 ($505/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,298 ($471/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,573 ($510/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,121 ($874/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,739 ($963/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,557 ($794/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,497 ($500/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,565 ($652/night)