Winter Timeshare Rentals in Hawaii

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$6,991 ($999/night)

Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 2
$4,930 ($704/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,113 ($1,016/night)

Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,137 ($734/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,911 ($844/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,107 ($872/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,306 ($472/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,039 ($720/night)

Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,565 ($652/night)

Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,222 ($603/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,039 ($720/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,129 ($876/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,252 ($750/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,374 ($625/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,110 ($1,016/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,680 ($526/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 5–11, 2026 (6 nights)
3 bed/2 bath, sleeps 8
$7,001 ($1,167/night)

Verified & Protected

Pono Kai

Kapaa, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,660 ($237/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$11,466 ($1,638/night)

Verified & Protected

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,793 ($828/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,726 ($532/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 3
$3,295 ($471/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,591 ($656/night)

Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,987 ($284/night)

Verified & Protected

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$8,745 ($1,249/night)

Verified & Protected

One Napili Way

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
3 bed/2 bath, sleeps 6
$2,423 ($346/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,385 ($626/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,167 ($595/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,603 ($658/night)

Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,314 ($331/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,622 ($517/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,513 ($502/night)

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,894 ($271/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,240 ($463/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,374 ($625/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,527 ($647/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$4,330 ($619/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$9,143 ($1,306/night)

Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,800 ($829/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,464 ($781/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,423 ($346/night)

Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,330 ($619/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,954 ($565/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)