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.
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,832 ($547/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
The Cliffs at Princeville
Princeville, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,742 ($249/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,268 ($467/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Pono Kai
Kapaa, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,769 ($253/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $2,696 ($385/night)
Pono Kai
Kapaa, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,802 ($543/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $2,505 ($358/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,268 ($467/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $3,039 ($434/night)
Pono Kai
Kapaa, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,588 ($227/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
- $1,925 ($275/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
The Point at Poipu
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,687 ($527/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
Kauai Beach Villas
Lihue, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $2,314 ($331/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,183 ($598/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 6–12, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($658/night)
Club Wyndham Shearwater
Princeville, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,756 ($679/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,361 ($766/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,489 ($641/night)
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 9–15, 2026 (6 nights)
- 3 bed/3 bath, sleeps 8
- $4,603 ($767/night)
Hanalei Bay Resort
Princeville, Hawaii- Dec 11–18, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,306 ($329/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 11–19, 2026 (8 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($684/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,816 ($974/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,794 ($685/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,565 ($652/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,649 ($521/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 11–17, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,557 ($593/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,268 ($467/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,886 ($412/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $3,535 ($505/night)
The Cliffs at Princeville
Princeville, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $4,031 ($576/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–16, 2026 (4 nights)
- 1 bed/2 bath, sleeps 4
- $1,550 ($388/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,268 ($467/night)
The Point at Poipu
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,657 ($380/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 12–18, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,851 ($642/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,283 ($612/night)