Winter Rentals
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,546 ($1,078/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,494 ($642/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–26, 2025 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,211 ($702/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 20–27, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
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Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,467 ($352/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,948 ($564/night)
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Paniolo Greens
Waikoloa Village, Hawaii- Dec 20–26, 2025 (6 nights)
- 2 bed/1 bath, sleeps 6
- $1,054 ($176/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,512 ($502/night)
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Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 20–27, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $2,123 ($303/night)
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Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,731 ($533/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $3,649 ($521/night)
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Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,493 ($642/night)
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Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,522 ($1,217/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,805 ($686/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,380 ($626/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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The Point at Poipu
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $944 ($135/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,835 ($548/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $2,205 ($315/night)
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Lifetime in Hawaii
Honolulu, Hawaii- Dec 20, 2025 – Jan 3, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($158/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,260 ($323/night)
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Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,094 ($728/night)
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Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,925 ($275/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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Pono Kai
Kapaa, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,987 ($284/night)
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Kohala Suites by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($626/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,385 ($198/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,432 ($1,062/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,631 ($1,233/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,478 ($354/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,494 ($642/night)
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The Point at Poipu
Koloa, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,568 ($510/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,512 ($502/night)
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Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,513 ($502/night)