Winter Rentals
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,603 ($658/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,601 ($1,372/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,199 ($1,171/night)
Verified & Protected
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $19,100 ($2,729/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,920 ($1,560/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,276 ($611/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,380 ($1,483/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 29, 2026 – Jan 5, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 30, 2026 – Jan 4, 2027 (5 nights)
- 1 bed/2 bath, sleeps 4
- $3,403 ($681/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,119 ($874/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,798 ($828/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,940 ($849/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,120 ($874/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,638 ($806/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,489 ($641/night)
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
Voted Top Pick 2025
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $16,375 ($2,339/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 12–19, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $11,470 ($1,639/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 27 – Mar 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,873 ($1,125/night)