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.
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 2–8, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($731/night)
Verified & Protected
WorldMark Kapaa Shore
Kapaa, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,613 ($802/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,599 ($657/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 3–11, 2027 (8 nights)
- 2 bed/2 bath, sleeps 6
- $3,687 ($461/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 3–8, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,431 ($686/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 7–11, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $2,118 ($529/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 7–11, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,839 ($460/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Jan 8–15, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,660 ($237/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 10–20, 2027 (10 nights)
- 2 bed/2 bath, sleeps 6
- $4,472 ($447/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 10–20, 2027 (10 nights)
- 2 bed/2 bath, sleeps 6
- $3,879 ($388/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 11–18, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 11–18, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 12–21, 2027 (9 nights)
- 2 bed/2 bath, sleeps 6
- $4,080 ($453/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 12–21, 2027 (9 nights)
- 2 bed/2 bath, sleeps 6
- $3,539 ($393/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,611 ($802/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,611 ($802/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 15–23, 2027 (8 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($494/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 15–23, 2027 (8 nights)
- 2 bed/2 bath, sleeps 6
- $3,426 ($428/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 15–22, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,039 ($434/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Jan 15–22, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,987 ($284/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,268 ($467/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Jan 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Jan 22–29, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,260 ($323/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($393/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($735/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,833 ($405/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,271 ($610/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)