Winter Timeshare Rentals in Hawaii (Big Island)

Verified & Protected

The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,657 ($380/night)

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Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 22–29, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,748 ($821/night)

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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)

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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)

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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)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,840 ($549/night)

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The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,153 ($450/night)

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Paniolo Greens

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,178 ($311/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,641 ($377/night)

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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)

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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)

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
$2,749 ($393/night)

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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

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,696 ($385/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
$2,967 ($424/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,022 ($432/night)

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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)

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
$6,565 ($938/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
$4,565 ($652/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
$2,696 ($385/night)

Verified & Protected

The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,202 ($743/night)

Verified & Protected

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)

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
$3,687 ($527/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
$21,389 ($3,056/night)

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Paniolo Greens

Waikoloa Village, Hawaii

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,543 ($363/night)

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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)

Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 28, 2026 – Jan 4, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$5,366 ($767/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

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 29, 2026 – Jan 5, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$5,366 ($767/night)

Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 30, 2026 – Jan 9, 2027 (10 nights)
1 bed/1 bath, sleeps 4
$8,091 ($809/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)

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Kona Coast Resort

Kailua-Kona, Hawaii

Jan 2–9, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,619 ($374/night)

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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)

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Paniolo Greens

Waikoloa Village, Hawaii

Jan 2–9, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,932 ($276/night)

Verified & Protected

Paniolo Greens

Waikoloa Village, Hawaii

Jan 2–9, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,025 ($289/night)

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Kona Coast Resort

Kailua-Kona, Hawaii

Jan 8–22, 2027 (14 nights)
1 bed/2 bath, sleeps 4
$4,058 ($290/night)

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WorldMark Kona Resort

Kailua-Kona, Hawaii

Jan 13–20, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,658 ($237/night)

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WorldMark Kona Resort

Kailua-Kona, Hawaii

Jan 14–24, 2027 (10 nights)
2 bed/2 bath, sleeps 6
$2,750 ($275/night)

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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)

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

WorldMark Kona Resort

Kailua-Kona, Hawaii

Jan 18–29, 2027 (11 nights)
2 bed/2 bath, sleeps 6
$2,965 ($270/night)

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Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Jan 23–30, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,020 ($860/night)

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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)

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The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

Feb 13–20, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,240 ($463/night)

Verified & Protected

Kona Coast Resort

Kailua-Kona, Hawaii

Feb 20–27, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,826 ($261/night)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Feb 20–27, 2027 (7 nights)
Studio/1 bath, sleeps 2
$3,840 ($549/night)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 18–25, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$21,825 ($3,118/night)

Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 25, 2027 – Jan 1, 2028 (7 nights)
Studio/1 bath, sleeps 4
$6,565 ($938/night)