Winter Timeshare Rentals in Hawaii (Big Island)

Verified & Protected

Club Wyndham Royal Sea Cliff

Kailua-Kona, Hawaii

Dec 2–7, 2026 (5 nights)
2 bed/2 bath, sleeps 6
$1,987 ($397/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,987 ($284/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,745 ($392/night)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 14–18, 2026 (4 nights)
2 bed/2 bath, sleeps 6
$10,925 ($2,731/night)

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Club Wyndham Kona Hawaiian Resort

Kailua-Kona, Hawaii

Dec 16–27, 2026 (11 nights)
2 bed/2 bath, sleeps 6
$5,366 ($488/night)

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Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 18–24, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$3,622 ($604/night)

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Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 18–23, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$4,325 ($865/night)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$6,222 ($889/night)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$21,825 ($3,118/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,167 ($595/night)

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Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,693 ($813/night)

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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)

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The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,186 ($455/night)

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Paniolo Greens

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,476 ($354/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,077 ($440/night)

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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)

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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)

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Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,540 ($791/night)

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Club Wyndham Kona Hawaiian Resort

Kailua-Kona, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,641 ($377/night)

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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)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$10,925 ($1,561/night)

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Club Wyndham Royal Sea Cliff

Kailua-Kona, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,295 ($471/night)

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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)

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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)

Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,290 ($1,327/night)

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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)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,748 ($821/night)

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The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,505 ($358/night)

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Paniolo Greens

Waikoloa Village, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,968 ($424/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
$15,285 ($2,184/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)

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)

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)

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)

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

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)

Verified & Protected

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
$2,750 ($393/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
$4,183 ($598/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
$4,276 ($611/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

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
$2,531 ($362/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
$4,977 ($711/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
$3,840 ($549/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
$4,374 ($625/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 6
$3,153 ($450/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
$3,840 ($549/night)