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 Cliffs at Princeville
Princeville, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,742 ($249/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,925 ($275/night)
Club Wyndham Shearwater
Princeville, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,489 ($641/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
Hanalei Bay Resort
Princeville, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,306 ($329/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 12–18, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,851 ($642/night)
The Cliffs at Princeville
Princeville, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $4,031 ($576/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,283 ($612/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,294 ($471/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,350 ($907/night)
Makai Club Resort
Princeville, Hawaii- Dec 17–23, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,478 ($413/night)
The Cliffs at Princeville
Princeville, Hawaii- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 12
- $7,274 ($1,039/night)
Club Wyndham Shearwater
Princeville, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
The Cliffs at Princeville
Princeville, Hawaii- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 1 bed/2 bath, sleeps 8
- $6,892 ($492/night)
The Cliffs at Princeville
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,679 ($668/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,214 ($1,031/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,053 ($865/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,732 ($819/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,543 ($363/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,709 ($816/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($412/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Hanalei Bay Resort
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,692 ($813/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,924 ($418/night)
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Club Wyndham Shearwater
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,543 ($363/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,023 ($718/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,692 ($813/night)
Hanalei Bay Resort
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,527 ($647/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 22–27, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,069 ($414/night)
Hanalei Bay Resort
Princeville, Hawaii- Dec 24–31, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,696 ($385/night)
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,734 ($391/night)
The Cliffs at Princeville
Princeville, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 4 bed/4 bath, sleeps 12
- $7,274 ($1,039/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
The Cliffs at Princeville
Princeville, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,987 ($284/night)
Club Wyndham Ka 'Eo Kai
Princeville, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
Hanalei Bay Resort
Princeville, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,901 ($700/night)