Winter Rentals
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 6–13, 2025 (7 nights)
- 3 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 12–19, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,548 ($650/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 12–19, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,707 ($672/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 12–19, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,132 ($447/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $1,877 ($268/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 14–19, 2025 (5 nights)
- Studio/1 bath, sleeps 4
- $2,150 ($430/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 14–21, 2025 (7 nights)
- 3 bed/3 bath, sleeps 10
- $6,778 ($968/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 14–21, 2025 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,650 ($1,093/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $2,478 ($354/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 15–22, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 15–26, 2025 (11 nights)
- 2 bed/2 bath, sleeps 8
- $8,527 ($775/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 15–21, 2025 (6 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($912/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 16–23, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,816 ($688/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 16–20, 2025 (4 nights)
- Studio/1 bath, sleeps 2
- $988 ($247/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 16–21, 2025 (5 nights)
- Studio/1 bath, sleeps 2
- $999 ($200/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 16–20, 2025 (4 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($166/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 16–28, 2025 (12 nights)
- 2 bed/2 bath, sleeps 8
- $10,920 ($910/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 16–23, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/night)
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Marriott's Waikoloa Ocean Club
Waikoloa Village, Hawaii- Dec 16–23, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,096 ($299/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 16–26, 2025 (10 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($656/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 17–21, 2025 (4 nights)
- Studio/1 bath, sleeps 4
- $888 ($222/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 17–21, 2025 (4 nights)
- Studio/1 bath, sleeps 2
- $1,110 ($278/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 17–20, 2025 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,099 ($366/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 17–20, 2025 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($553/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 17–21, 2025 (4 nights)
- Studio/1 bath, sleeps 4
- $555 ($139/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 18–21, 2025 (3 nights)
- Studio/1 bath, sleeps 4
- $999 ($333/night)
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Lawai Beach Resort
Koloa, Hawaii- Dec 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,768 ($253/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 18–21, 2025 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,054 ($352/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 18–23, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($1,030/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 18, 2025 – Jan 1, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $4,603 ($329/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 18–23, 2025 (5 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($659/night)
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Lawai Beach Resort
Koloa, Hawaii- Dec 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,205 ($315/night)
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Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 18–21, 2025 (3 nights)
- 1 bed/1 bath, sleeps 4
- $777 ($259/night)
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Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,493 ($642/night)
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Kahana Villa Resort
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,493 ($642/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,966 ($852/night)
Verified & Protected
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–27, 2025 (8 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($303/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($1,249/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,384 ($626/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,200 ($1,171/night)