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.
Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,072 ($439/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)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,306 ($329/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,001 ($429/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 Point at Poipu
Koloa, Hawaii- Jan 2–8, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($549/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 Point at Poipu
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,599 ($657/night)
The Cliffs at Princeville
Princeville, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/night)
WorldMark Kapaa Shore
Kapaa, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,543 ($363/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/night)
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,938 ($848/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 7–10, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $2,968 ($989/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)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/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 11–14, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,198 ($399/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 14–17, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,725 ($575/night)
Lawai Beach Resort
Koloa, Hawaii- Jan 14–28, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $6,205 ($443/night)
The Point at Poipu
Koloa, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,687 ($527/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 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,764 ($395/night)
Lawai Beach Resort
Koloa, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,619 ($374/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,886 ($412/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,031 ($576/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 19–22, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,198 ($399/night)
Lawai Beach Resort
Koloa, Hawaii- Jan 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,581 ($369/night)
Lawai Beach Resort
Koloa, Hawaii- Jan 21 – Feb 4, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $6,205 ($443/night)
The Cliffs at Princeville
Princeville, Hawaii- Jan 22–29, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,260 ($323/night)
The Point at Poipu
Koloa, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,314 ($331/night)
Lawai Beach Resort
Koloa, Hawaii- Jan 28 – Feb 4, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,619 ($374/night)
Lawai Beach Resort
Koloa, Hawaii- Jan 28 – Feb 4, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,657 ($380/night)
The Cliffs at Princeville
Princeville, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)