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
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,910 ($844/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,750 ($393/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
- $5,475 ($782/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 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,123 ($303/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
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
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
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
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
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,039 ($720/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
- $5,748 ($821/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
The Point at Poipu
Koloa, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/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 Point at Poipu
Koloa, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/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
Wyndham Kauai Coast Resort at the Beachboy
Kapaa, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/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)
The Point at Poipu
Koloa, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,489 ($641/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
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 5–12, 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- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $2,917 ($417/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,420 ($774/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,730 ($533/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,992 ($999/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,992 ($999/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $3,077 ($440/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,204 ($315/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,963 ($423/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 15–22, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,384 ($626/night)