Winter Rentals
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,546 ($1,078/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,423 ($346/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,821 ($689/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,858 ($408/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($424/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,949 ($564/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
Kahana Falls
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,550 ($221/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,039 ($434/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($455/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,598 ($1,514/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,873 ($1,125/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Hono Koa Resort
Honokowai, Hawaii- Feb 28 – Mar 14, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $5,351 ($382/night)
Verified & Protected
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,437 ($1,062/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,294 ($471/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,632 ($1,090/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 1–8, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,911 ($844/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,330 ($619/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 15–22, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,838 ($977/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,560 ($937/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,112 ($588/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,358 ($765/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $13,650 ($1,950/night)
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $13,105 ($1,872/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,272 ($1,039/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,835 ($1,405/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,380 ($1,483/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $15,285 ($1,092/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $21,847 ($1,560/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 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 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,330 ($619/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,854 ($1,265/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,112 ($588/night)
Verified & Protected
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,257 ($751/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,565 ($938/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $19,100 ($2,729/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,690 ($1,242/night)