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)
3 bed/3 bath, sleeps 10
$10,925 ($1,561/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
$5,748 ($821/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 Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,020 ($860/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

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,976 ($568/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
$3,350 ($478/night)

Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,347 ($907/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
$6,129 ($876/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

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

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,557 ($794/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–11, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$3,687 ($615/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 5–11, 2026 (6 nights)
2 bed/3 bath, sleeps 8
$4,984 ($831/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 Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,112 ($588/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)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,603 ($658/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

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,458 ($494/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
$6,560 ($937/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

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,676 ($525/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

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

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 5–14, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$7,088 ($788/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,385 ($626/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)

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 - Lahaina Tower

Lahaina, Hawaii

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,290 ($1,327/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
$3,840 ($549/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
$2,917 ($417/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
$4,450 ($636/night)

Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Dec 6–13, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,807 ($544/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,906 ($844/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,557 ($794/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 6–10, 2026 (4 nights)
Studio/1 bath, sleeps 4
$2,327 ($582/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,519 ($788/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,938 ($848/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,336 ($619/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,750 ($393/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected

Paniolo Greens

Waikoloa Village, Hawaii

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,932 ($276/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,290 ($470/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,829 ($547/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 6–13, 2026 (7 nights)
Studio/1 bath, sleeps 2
$2,204 ($315/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 6–11, 2026 (5 nights)
3 bed/3 bath, sleeps 10
$5,475 ($1,095/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,999 ($428/night)