Winter Rentals
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 18–21, 2025 (3 nights)
- 1 bed/1 bath, sleeps 4
- $777 ($259/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 18–21, 2025 (3 nights)
- Studio/1 bath, sleeps 4
- $999 ($333/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 18–21, 2025 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,054 ($352/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 18–23, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($1,030/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 18–25, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,768 ($253/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($1,249/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,290 ($470/night)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,200 ($1,171/night)
Verified & Protected
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,380 ($626/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,240 ($463/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
Verified & Protected
Kahana Villa Resort
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
The Cliffs at Princeville
Princeville, Hawaii- Dec 19–26, 2025 (7 nights)
- 4 bed/4 bath, sleeps 10
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,731 ($533/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $686,725 ($98,104/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,384 ($626/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($237/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,478 ($354/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($1,249/night)
Verified & Protected
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,358 ($765/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,450 ($636/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,072 ($439/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2025 (7 nights)
- Studio/1 bath, sleeps 2
- $1,535 ($219/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,384 ($626/night)
Verified & Protected
Club Wyndham Royal Sea Cliff
Kailua-Kona, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–27, 2025 (8 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($303/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,493 ($642/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 19–27, 2025 (8 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($276/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,966 ($852/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,489 ($641/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,493 ($642/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)