Winter Rentals
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 21–25, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,412 ($353/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Feb 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,148 ($735/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
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)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Feb 21–24, 2026 (3 nights)
- 2 bed/2 bath, sleeps 6
- $2,750 ($917/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $2,531 ($362/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,568 ($510/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $3,949 ($564/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,091 ($870/night)
Verified & Protected
Maui Banyan Vacation Club
Kihei, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,085 ($298/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 22–28, 2026 (6 nights)
- 3 bed/2 bath, sleeps 8
- $6,565 ($1,094/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 22 – Mar 1, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 23–27, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($578/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 23 – Mar 2, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,511 ($502/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 24 – Mar 2, 2026 (6 nights)
- Studio/1 bath, sleeps 2
- $2,205 ($368/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 24–28, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,636 ($659/night)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Feb 24 – Mar 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,276 ($325/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 25 – Mar 4, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,467 ($352/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Feb 25 – Mar 4, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($190/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,696 ($385/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 27 – Mar 6, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,458 ($494/night)
Verified & Protected
Kahana Falls
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,385 ($198/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,366 ($767/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 21, 2026 (21 nights)
- 1 bed/2 bath, sleeps 4
- $7,655 ($365/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,470 ($781/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,797 ($828/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,238 ($320/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $13,378 ($1,911/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 28 – Mar 6, 2026 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,821 ($804/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,422 ($346/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
- $7,655 ($1,094/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
- $9,617 ($1,374/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,167 ($595/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,519 ($788/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Feb 28 – Mar 7, 2026 (7 nights)
- 2 bed/1 bath, sleeps 6
- $3,295 ($471/night)