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
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
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
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
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 14–20, 2025 (6 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($277/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,701 ($957/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($284/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- 2 bed/3 bath, sleeps 8
- $3,132 ($447/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- 2 bed/3 bath, sleeps 8
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 14–18, 2025 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($415/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $2,914 ($416/night)
Verified & Protected
Kahana Villa Resort
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,109 ($158/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 14–21, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $944 ($135/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,309 ($1,187/night)
Verified & Protected
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)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Kuhio Banyan Club
Honolulu, Hawaii- Dec 14–21, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $832 ($119/night)
Verified & Protected
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)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,892 ($413/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 14–21, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
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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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 14–19, 2025 (5 nights)
- Studio/1 bath, sleeps 2
- $1,385 ($277/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 14–20, 2025 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($458/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 15–20, 2025 (5 nights)
- 1 bed/2 bath, sleeps 4
- $1,385 ($277/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)
Verified & Protected
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)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 15–20, 2025 (5 nights)
- 3 bed/3 bath, sleeps 12
- $13,210 ($2,642/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
- $2,423 ($346/night)
Verified & Protected
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
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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Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 16–23, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($393/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
- $1,110 ($278/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 16–21, 2025 (5 nights)
- Studio/1 bath, sleeps 2
- $999 ($200/night)
Verified & Protected
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 16–26, 2025 (10 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($656/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
- $832 ($208/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 17–21, 2025 (4 nights)
- Studio/1 bath, sleeps 4
- $888 ($222/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 17–20, 2025 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,099 ($366/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 17–21, 2025 (4 nights)
- Studio/1 bath, sleeps 2
- $1,110 ($278/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 17–20, 2025 (3 nights)
- 2 bed/2 bath, sleeps 8
- $2,298 ($766/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)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,768 ($253/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)