Winter Rentals
Verified & Protected
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
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 Nanea Ocean Villas
Lahaina, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $20,626 ($2,947/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)
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)
Verified & Protected
Kahana Villa Resort
Lahaina, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,185 ($455/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,276 ($325/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/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
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 27, 2025 – Jan 1, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,204 ($441/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,147 ($735/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/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
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,004 ($572/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $10,920 ($1,560/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)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,147 ($735/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,995 ($1,571/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 28, 2025 – Jan 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,500 ($1,929/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 30, 2025 – Jan 6, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 1–8, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,749 ($393/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,970 ($424/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,998 ($857/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,276 ($611/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,001 ($1,000/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,949 ($564/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2026 (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- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,358 ($765/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,786 ($541/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,294 ($471/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,303 ($329/night)