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.
Maui Beach Vacation Club
Kihei, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,650 ($236/night)
Maui Schooner
Kihei, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $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)
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)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,206 ($744/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Maui Schooner
Kihei, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $10,867 ($1,552/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $14,195 ($2,028/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,015 ($859/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,595 ($656/night)
WorldMark Kihei Resort
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,856 ($265/night)
Maui Beach Vacation Club
Kihei, Hawaii- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $3,306 ($236/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,527 ($647/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,687 ($670/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,901 ($700/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,679 ($668/night)
Maui Schooner
Kihei, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($221/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,090 ($1,013/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,112 ($588/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $11,470 ($1,639/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,110 ($1,016/night)
Maui Banyan Vacation Club
Kihei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Maui Lea at Maui Hill
Kihei, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,421 ($346/night)
Kamaole Beach Club
Kihei, Hawaii- Jan 16–30, 2027 (14 nights)
- 1 bed/1.5 bath, sleeps 4
- $4,603 ($329/night)
Maui Beach Vacation Club
Kihei, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,848 ($407/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Maui Lea at Maui Hill
Kihei, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Maui Schooner
Kihei, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,818 ($260/night)
Maui Schooner
Kihei, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,818 ($260/night)
Maui Banyan Vacation Club
Kihei, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,200 ($314/night)
Maui Beach Vacation Club
Kihei, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,467 ($352/night)
Maui Banyan Vacation Club
Kihei, Hawaii- Feb 7–14, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,039 ($434/night)
Maui Banyan Vacation Club
Kihei, Hawaii- Feb 12–19, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $1,550 ($221/night)
Maui Beach Vacation Club
Kihei, Hawaii- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,123 ($303/night)
Maui Banyan Vacation Club
Kihei, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $1,550 ($221/night)
Maui Schooner
Kihei, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,818 ($260/night)
Maui Schooner
Kihei, Hawaii- Dec 26, 2027 – Jan 2, 2028 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)