Winter Rentals
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,707 ($672/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,143 ($735/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 8–13, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($790/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $7,655 ($1,094/night)
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Kahana Beach Resort
Lahaina, Hawaii- Feb 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($284/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,423 ($346/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,968 ($424/night)
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The Cliffs at Princeville
Princeville, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,165 ($166/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($424/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,465 ($209/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,948 ($564/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,204 ($315/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,252 ($750/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $61,010 ($8,716/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,112 ($588/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,949 ($564/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,839 ($406/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $15,285 ($2,184/night)
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Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 14–21, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,641 ($377/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,200 ($1,171/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,015 ($1,716/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 14–21, 2026 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $6,564 ($938/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,778 ($968/night)
Verified & Protected
Maui Banyan Vacation Club
Kihei, Hawaii- Feb 15–22, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,085 ($298/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 15–22, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,696 ($385/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 15–22, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,422 ($346/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 17–24, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,053 ($579/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 17–27, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($766/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 17–20, 2026 (3 nights)
- 1 bed/1 bath, sleeps 5
- $2,000 ($667/night)
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The Bay Club at Waikoloa Beach
Waikoloa Village, Hawaii- Feb 20–24, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,110 ($278/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,420 ($774/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
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Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Feb 21 – Mar 1, 2026 (8 nights)
- 1 bed/1 bath, sleeps 4
- $2,554 ($319/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,058 ($580/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,966 ($852/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,148 ($735/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($253/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Feb 21–28, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,110 ($159/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,290 ($1,327/night)