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.
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $4,930 ($704/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/night)
Paniolo Greens
Waikoloa Village, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,704 ($243/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $24,006 ($3,429/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $15,285 ($2,184/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,276 ($325/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,924 ($418/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 14–18, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($2,186/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 16–23, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $4,603 ($658/night)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 18–23, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $3,562 ($712/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,993 ($570/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,696 ($385/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $16,048 ($2,293/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $15,285 ($2,184/night)
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,046 ($721/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,832 ($690/night)
Paniolo Greens
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,742 ($249/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,664 ($809/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,963 ($423/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
Kohala Suites by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,505 ($358/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
Paniolo Greens
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,925 ($275/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,274 ($1,039/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,949 ($564/night)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,540 ($791/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $14,904 ($2,129/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Kohala Suites by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,222 ($603/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,598 ($657/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)
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)
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)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 22–29, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,984 ($712/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)
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)