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.
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 5–10, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($572/night)
Verified & Protected
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,183 ($312/night)
Club Wyndham Kona Hawaiian Resort
Kailua-Kona, Hawaii- Dec 16–27, 2026 (11 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($488/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 18–24, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($604/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 18–23, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $4,325 ($865/night)
Verified & Protected
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)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,380 ($1,483/night)
Verified & Protected
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,925 ($704/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,540 ($791/night)
Verified & Protected
Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,693 ($813/night)
Verified & Protected
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)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,265 ($609/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,257 ($751/night)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,712 ($673/night)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,312 ($759/night)
Verified & Protected
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,380 ($626/night)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,470 ($781/night)
Verified & Protected
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)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
Verified & Protected
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)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,948 ($658/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 29, 2026 – Jan 5, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,946 ($992/night)
Verified & Protected
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)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Jan 2–9, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($658/night)
Verified & Protected
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($588/night)
Verified & Protected
Kona Coast Resort
Kailua-Kona, Hawaii- Jan 8–22, 2027 (14 nights)
- 1 bed/2 bath, sleeps 4
- $4,058 ($290/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,166 ($595/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,984 ($712/night)
Verified & Protected
Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Feb 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,707 ($672/night)