Winter Timeshare Rentals in Hawaii

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 6–13, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$3,949 ($564/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
$4,112 ($588/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
$6,620 ($946/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
$4,930 ($704/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
$3,649 ($521/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 Ko Olina Beach Club

Kapolei, Hawaii

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,732 ($962/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)
Studio/1 bath, sleeps 2
$2,204 ($315/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 6–13, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$10,380 ($1,483/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 7–14, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,938 ($848/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 7–14, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,282 ($897/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 8–15, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$6,402 ($914/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 8–15, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$6,402 ($914/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 8–15, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$6,402 ($914/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 9–16, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,783 ($969/night)

Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 9–19, 2026 (10 nights)
Studio/1 bath, sleeps 2
$3,813 ($381/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 9–16, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$9,246 ($1,321/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 9–20, 2026 (11 nights)
2 bed/2 bath, sleeps 8
$10,816 ($983/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 10–18, 2026 (8 nights)
3 bed/2 bath, sleeps 8
$10,870 ($1,359/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 10–14, 2026 (4 nights)
Studio/1 bath, sleeps 4
$2,327 ($582/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 11–18, 2026 (7 nights)
Studio/1 bath, sleeps 2
$3,295 ($471/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$9,835 ($1,405/night)

Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 11–18, 2026 (7 nights)
Studio/1 bath, sleeps 2
$3,295 ($471/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,611 ($516/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,600 ($1,086/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$8,309 ($1,187/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$9,835 ($1,405/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 11–18, 2026 (7 nights)
Studio/1 bath, sleeps 2
$2,750 ($393/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,478 ($354/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 11–14, 2026 (3 nights)
Studio/1 bath, sleeps 4
$1,859 ($620/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,930 ($704/night)

Verified & Protected

The Cliffs at Princeville

Princeville, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/2 bath, sleeps 6
$4,222 ($603/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,112 ($588/night)

Verified & Protected

The Point at Poipu

Koloa, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$6,456 ($922/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,077 ($440/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,676 ($525/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,240 ($463/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,404 ($486/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 12–15, 2026 (3 nights)
Studio/1 bath, sleeps 4
$1,752 ($584/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 12–19, 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 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,110 ($1,016/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
Studio/1 bath, sleeps 4
$4,053 ($579/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,320 ($903/night)