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)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/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)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
The Point at Poipu
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,687 ($527/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,183 ($598/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 Waiohai Beach Club
Koloa, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,361 ($766/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 6–12, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $3,949 ($658/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,756 ($679/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 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
- $4,794 ($685/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,649 ($521/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 11–19, 2026 (8 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($684/night)
The Point at Poipu
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,527 ($647/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,110 ($1,016/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)
- 2 bed/2 bath, sleeps 6
- $6,121 ($874/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
- $3,840 ($549/night)
The Point at Poipu
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
The Point at Poipu
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,977 ($711/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,031 ($576/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,031 ($576/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($549/night)
The Point at Poipu
Koloa, Hawaii- Dec 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,478 ($413/night)
Lawai Beach Resort
Koloa, Hawaii- Dec 17–31, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($547/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,674 ($953/night)
The Point at Poipu
Koloa, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
Lawai Beach Resort
Koloa, Hawaii- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($383/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,687 ($527/night)
The Point at Poipu
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,094 ($728/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,884 ($983/night)