Winter Rentals in Hawaii

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Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 22–25, 2025 (3 nights)
1 bed/2 bath, sleeps 4
$1,165 ($388/night)

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Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 23–30, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$3,404 ($486/night)

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Marriott Vacation Club, Waikiki

Honolulu, Hawaii

Dec 23–28, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$10,925 ($2,185/night)

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Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 23–28, 2025 (5 nights)
Studio/1 bath, sleeps 2
$2,205 ($441/night)

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Club Wyndham Bali Hai Villas

Princeville, Hawaii

Dec 23–26, 2025 (3 nights)
2 bed/2 bath, sleeps 6
$999 ($333/night)

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Club Wyndham at Waikiki Beach Walk

Honolulu, Hawaii

Dec 24–27, 2025 (3 nights)
1 bed/1 bath, sleeps 4
$1,275 ($425/night)

Verified & Protected Voted Top Pick 2025

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 24–26, 2025 (2 nights)
2 bed/2 bath, sleeps 8
$2,205 ($1,102/night)

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 24–28, 2025 (4 nights)
1 bed/1 bath, sleeps 4
$1,330 ($332/night)

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Marriott Vacation Club, Waikiki

Honolulu, Hawaii

Dec 24, 2025 – Jan 1, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$7,219 ($902/night)

Verified & Protected Voted Top Pick 2025

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 25–27, 2025 (2 nights)
1 bed/1 bath, sleeps 4
$1,605 ($802/night)

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Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,303 ($329/night)

Verified & Protected Voted Top Pick 2025

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$13,100 ($1,871/night)

Verified & Protected Voted Top Pick 2025

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$15,285 ($2,184/night)

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Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 26–29, 2025 (3 nights)
Studio/1 bath, sleeps 4
$2,423 ($808/night)

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 26–29, 2025 (3 nights)
1 bed/1 bath, sleeps 4
$1,330 ($443/night)

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The Bay Club at Waikoloa Beach

Waikoloa Village, Hawaii

Dec 26, 2025 – Jan 3, 2026 (8 nights)
2 bed/2 bath, sleeps 6
$3,513 ($439/night)

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The Cliffs at Princeville

Princeville, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
4 bed/4 bath, sleeps 10
$4,603 ($658/night)

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Makai Club Resort

Princeville, Hawaii

Dec 26, 2025 – Jan 9, 2026 (14 nights)
1 bed/1 bath, sleeps 4
$4,385 ($313/night)

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The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,186 ($455/night)

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Kahana Villa Resort

Lahaina, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,968 ($424/night)

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The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,497 ($1,071/night)

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The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,423 ($346/night)

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Lawai Beach Resort

Koloa, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,495 ($214/night)

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The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,949 ($421/night)

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Lawai Beach Resort

Koloa, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,659 ($237/night)

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Marriott Vacation Club, Waikiki

Honolulu, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
1 bed/1 bath, sleeps 6
$2,924 ($418/night)

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Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,368 ($338/night)

Verified & Protected Voted Top Pick 2025

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$20,626 ($2,947/night)

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Club Wyndham Bali Hai Villas

Princeville, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,205 ($315/night)

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Club Wyndham Bali Hai Villas

Princeville, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,201 ($314/night)

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Lawai Beach Resort

Koloa, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,042 ($292/night)

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 26, 2025 – Jan 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,423 ($346/night)

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Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,835 ($548/night)

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,873 ($1,125/night)

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Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,532 ($362/night)

Verified & Protected Voted Top Pick 2025

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,763 ($1,109/night)

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Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Dec 27, 2025 – Jan 2, 2026 (6 nights)
Studio/1 bath, sleeps 4
$3,077 ($513/night)

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Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,395 ($628/night)

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Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,750 ($393/night)

Voted Top Pick 2025

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,655 ($1,094/night)

Verified & Protected Voted Top Pick 2025

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$10,995 ($1,571/night)

Verified & Protected Voted Top Pick 2025

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,418 ($1,203/night)

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Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,750 ($393/night)

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Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,458 ($494/night)

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Club Wyndham Royal Sea Cliff

Kailua-Kona, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,983 ($283/night)

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Hanalei Bay Resort

Princeville, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,622 ($517/night)

Verified & Protected Voted Top Pick 2025

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,930 ($704/night)

Verified & Protected Voted Top Pick 2025

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$13,500 ($1,929/night)