Winter Rentals
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 30, 2025 – Jan 4, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($266/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 31, 2025 – Jan 4, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $5,250 ($1,313/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 31, 2025 – Jan 5, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,712 ($942/night)
Verified & Protected
Kona Coast Resort
Kailua-Kona, Hawaii- Dec 31, 2025 – Jan 7, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/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
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/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
- $5,998 ($857/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)
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,510 ($930/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($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 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 Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Jan 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,186 ($455/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
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,557 ($794/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
Lahaina, Hawaii- Jan 3–10, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/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
Kalia Suites by Hilton Grand Vacations
Honolulu, Hawaii- Jan 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,769 ($253/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
Lawai Beach Resort
Koloa, Hawaii- Jan 3–17, 2026 (14 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($294/night)
Verified & Protected
Paniolo Greens
Waikoloa Village, Hawaii- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $999 ($143/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
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
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,313 ($330/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
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–8, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($986/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,929 ($704/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
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
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,204 ($315/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,110 ($1,016/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)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,252 ($750/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
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 4–7, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,440 ($480/night)
Verified & Protected
The Point at Poipu
Koloa, Hawaii- Jan 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,641 ($377/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/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
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)