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.
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Club Wyndham Mauna Loa Village
Kailua-Kona, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,085 ($298/night)
Kohala Suites by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($331/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,175 ($739/night)
Paniolo Greens
Waikoloa Village, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,543 ($363/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 20–26, 2026 (6 nights)
- Studio/1 bath, sleeps 2
- $3,295 ($549/night)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,984 ($712/night)
Kohala Suites by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 22–29, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 24–31, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
Club Wyndham Holua Resort at the Mauna Loa Village
Kailua-Kona, Hawaii- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,595 ($656/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,421 ($346/night)
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,543 ($363/night)
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,528 ($361/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Paniolo Greens
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,627 ($232/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,636 ($662/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,967 ($424/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,804 ($401/night)
WorldMark Kona Resort
Kailua-Kona, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,202 ($743/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,202 ($743/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,749 ($393/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($424/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,428 ($347/night)
Paniolo Greens
Waikoloa Village, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,543 ($363/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,185 ($455/night)
Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Dec 28, 2026 – Jan 3, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($331/night)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 29, 2026 – Jan 5, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,129 ($876/night)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 30, 2026 – Jan 9, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $7,099 ($710/night)
Kona Coast Resort
Kailua-Kona, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,467 ($352/night)
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,707 ($1,530/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Jan 3–9, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $2,183 ($364/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Jan 4–11, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
Kona Coast Resort
Kailua-Kona, Hawaii- Jan 7–14, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,742 ($249/night)
Kona Coast Resort
Kailua-Kona, Hawaii- Jan 8–22, 2027 (14 nights)
- 1 bed/2 bath, sleeps 4
- $4,058 ($290/night)
WorldMark Kona Resort
Kailua-Kona, Hawaii- Jan 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,542 ($220/night)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Jan 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
WorldMark Kona Resort
Kailua-Kona, Hawaii- Jan 14–24, 2027 (10 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($275/night)
Kona Coast Resort
Kailua-Kona, Hawaii- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,742 ($249/night)
Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Jan 15–22, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,840 ($406/night)
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Jan 15–29, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $8,963 ($640/night)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,166 ($595/night)
WorldMark Kona Resort
Kailua-Kona, Hawaii- Jan 18–29, 2027 (11 nights)
- 2 bed/2 bath, sleeps 6
- $2,965 ($270/night)