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.
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,701 ($957/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,527 ($647/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,832 ($690/night)
The Cliffs at Princeville
Princeville, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,894 ($271/night)
Hanalei Bay Resort
Princeville, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,696 ($385/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,121 ($874/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,565 ($652/night)
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $3,840 ($549/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Club Wyndham Shearwater
Princeville, Hawaii- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Hanalei Bay Resort
Princeville, Hawaii- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,696 ($385/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,595 ($656/night)
The Cliffs at Princeville
Princeville, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,099 ($728/night)
The Cliffs at Princeville
Princeville, Hawaii- Jan 8–15, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,660 ($237/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,365 ($1,052/night)
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($386/night)
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 11–15, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,594 ($398/night)
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 11–14, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,198 ($399/night)
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 14–17, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,725 ($575/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,764 ($395/night)
The Cliffs at Princeville
Princeville, Hawaii- Jan 15–22, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,987 ($284/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/night)
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 19–22, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,198 ($399/night)
The Cliffs at Princeville
Princeville, Hawaii- Jan 22–29, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,260 ($323/night)
The Cliffs at Princeville
Princeville, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 1–7, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,445 ($407/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 5–13, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($657/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Feb 7–15, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($166/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 8–14, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,440 ($740/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 11–18, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 12–19, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,688 ($384/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,824 ($689/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,993 ($428/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,252 ($750/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,810 ($401/night)