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 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)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,268 ($467/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,505 ($358/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
- $4,977 ($711/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
- $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)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $3,535 ($505/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/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 Kauai Beach Club
Lihue, Hawaii- Dec 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $2,968 ($424/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)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,350 ($907/night)
The Point at Poipu
Koloa, Hawaii- Dec 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,478 ($413/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($549/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 16–23, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,684 ($383/night)
Lawai Beach Resort
Koloa, Hawaii- Dec 17–31, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($547/night)
Makai Club Resort
Princeville, Hawaii- Dec 17–23, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,478 ($413/night)
The Point at Poipu
Koloa, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
The Cliffs at Princeville
Princeville, Hawaii- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 1 bed/2 bath, sleeps 8
- $6,892 ($492/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 Cliffs at Princeville
Princeville, Hawaii- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 12
- $7,274 ($1,039/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 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,513 ($502/night)
Club Wyndham Shearwater
Princeville, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,511 ($787/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,968 ($424/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,687 ($527/night)
Pono Kai
Kapaa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,780 ($254/night)
Pono Kai
Kapaa, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($166/night)
Pono Kai
Kapaa, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($166/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/night)
Pono Kai
Kapaa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,780 ($254/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,213 ($745/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,000 ($714/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,458 ($494/night)
The Point at Poipu
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $16,374 ($1,170/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,320 ($903/night)