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 Nanea Ocean Villas
Lahaina, Hawaii- Dec 1–6, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $3,121 ($624/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 1–6, 2026 (5 nights)
- 1 bed/2 bath, sleeps 4
- $2,478 ($496/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 1–6, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($485/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 1–8, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,911 ($844/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 1–6, 2026 (5 nights)
- 1 bed/2 bath, sleeps 4
- $2,478 ($496/night)
Kahana Falls
Lahaina, Hawaii- Dec 3–10, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,096 ($299/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 4–7, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $832 ($278/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 4–9, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $1,632 ($326/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,473 ($782/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,649 ($521/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,619 ($374/night)
Maui Beach Vacation Club
Kihei, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,650 ($236/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)
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)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/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)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,793 ($828/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)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,451 ($493/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $8,036 ($1,148/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,894 ($271/night)
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)
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $2,314 ($331/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)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
Maui Schooner
Kihei, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $1,932 ($276/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/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)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/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)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,123 ($303/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,031 ($576/night)
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,214 ($602/night)
One Napili Way
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/2 bath, sleeps 6
- $1,932 ($276/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
- $3,240 ($463/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,374 ($625/night)