Winter Rentals
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)
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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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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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)
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Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 18–21, 2025 (3 nights)
- 1 bed/1 bath, sleeps 4
- $832 ($278/night)
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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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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)
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Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,380 ($626/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,384 ($626/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 3 bed/2 bath, sleeps 8
- $13,105 ($1,872/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)
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
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
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,963 ($423/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)
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Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($237/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
- $20,626 ($2,947/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
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($1,249/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $686,725 ($98,104/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
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/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
- $3,458 ($494/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/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)
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
- $3,072 ($439/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,731 ($533/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
- $7,110 ($1,016/night)
Verified & Protected
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 Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,094 ($728/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/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
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($564/night)
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Dec 20–23, 2025 (3 nights)
- 2 bed/2 bath, sleeps 6
- $2,313 ($771/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)
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
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)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,658 ($665/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
- $6,020 ($860/night)
Verified & Protected
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)
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)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,829 ($833/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,742 ($249/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 20–27, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,878 ($268/night)