Winter Timeshare Rentals in Hawaii

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
$3,731 ($533/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

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,924 ($418/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
$3,399 ($486/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
$5,557 ($794/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
$3,458 ($494/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 12–18, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$2,641 ($440/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,911 ($844/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,222 ($603/night)

Verified & Protected

Hanalei Bay Resort

Princeville, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$2,314 ($331/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,633 ($805/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 13–18, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$2,069 ($414/night)

Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

Dec 13–19, 2026 (6 nights)
2 bed/2 bath, sleeps 6
$2,292 ($382/night)

Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

Dec 13–19, 2026 (6 nights)
2 bed/2 bath, sleeps 6
$2,641 ($440/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,105 ($1,015/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 13–18, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$2,450 ($490/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 13–20, 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 13–18, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$3,840 ($768/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,731 ($533/night)

Verified & Protected

Maui Schooner

Kihei, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,161 ($309/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,276 ($611/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,712 ($673/night)

Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

Dec 13–16, 2026 (3 nights)
2 bed/2 bath, sleeps 6
$1,039 ($346/night)

Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

Dec 13–16, 2026 (3 nights)
2 bed/2 bath, sleeps 6
$1,198 ($399/night)

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,200 ($314/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,478 ($354/night)

Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,295 ($471/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,795 ($685/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$2,423 ($346/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$5,801 ($829/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 13–20, 2026 (7 nights)
Studio/1 bath, sleeps 2
$2,531 ($362/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$5,993 ($856/night)

Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,859 ($408/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 13–18, 2026 (5 nights)
Studio/1 bath, sleeps 4
$3,082 ($616/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,328 ($618/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,276 ($611/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,655 ($1,094/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,012 ($287/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,412 ($630/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,382 ($1,055/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 13–20, 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 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,929 ($704/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,385 ($626/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 13–20, 2026 (7 nights)
Studio/1 bath, sleeps 3
$2,968 ($424/night)

Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Dec 13–20, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 13–20, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,385 ($626/night)