Winter Rentals
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 1 bed/1 bath, sleeps 6
- $1,932 ($276/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,368 ($338/night)
Verified & Protected
Kahana Villa Resort
Lahaina, Hawaii- Dec 26, 2025 – Jan 2, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,968 ($424/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($408/night)
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,873 ($1,125/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,276 ($325/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,995 ($1,571/night)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($517/night)
Verified & Protected
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $10,924 ($1,561/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 27, 2025 – Jan 1, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,385 ($277/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,395 ($628/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,995 ($714/night)
Verified & Protected
Club Wyndham at Waikiki Beach Walk
Honolulu, Hawaii- Dec 27, 2025 – Jan 1, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,987 ($397/night)
Verified & Protected
Kona Coast Resort
Kailua-Kona, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,512 ($216/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,250 ($464/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 27, 2025 – Jan 6, 2026 (10 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($602/night)
Verified & Protected
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $14,995 ($2,142/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 27, 2025 – Jan 2, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($513/night)
Verified & Protected
Maui Schooner
Kihei, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,314 ($331/night)
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,835 ($548/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $14,995 ($2,142/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Hawaiian Sun Holidays
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 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
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,500 ($1,929/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,995 ($571/night)
Verified & Protected
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,500 ($1,071/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,987 ($284/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,527 ($1,218/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,641 ($377/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 27, 2025 – Jan 1, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,204 ($441/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,000 ($1,000/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,995 ($1,856/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,783 ($969/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,009 ($287/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $10,920 ($1,560/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,147 ($735/night)
Verified & Protected
Voted Top Pick 2025
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,995 ($285/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,470 ($781/night)
Verified & Protected
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 27, 2025 – Jan 3, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)