Winter Timeshare Rentals in Hawaii

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$8,058 ($1,151/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

Sands of Kahana Vacation Club

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$3,832 ($547/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,494 ($642/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,211 ($602/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,252 ($750/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
$3,382 ($483/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,832 ($547/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 11–16, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$4,385 ($877/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

Sands of Kahana Vacation Club

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,835 ($548/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,243 ($892/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

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,977 ($711/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 12–16, 2026 (4 nights)
1 bed/2 bath, sleeps 4
$1,769 ($442/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,294 ($471/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
$3,486 ($498/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
$4,602 ($657/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,995 ($428/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,358 ($765/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,602 ($657/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
$3,568 ($510/night)

Verified & Protected

The Cliffs at Princeville

Princeville, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/2 bath, sleeps 6
$4,031 ($576/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
$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

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

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 12–19, 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 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,693 ($813/night)

Verified & Protected

The Point at Poipu

Koloa, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,077 ($440/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
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,202 ($743/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
$7,502 ($1,072/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,603 ($658/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)
1 bed/1 bath, sleeps 4
$3,568 ($510/night)

Verified & Protected

Sands of Kahana Vacation Club

Lahaina, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,772 ($396/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

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

Verified & Protected

Sheraton Kauai Resort Villas

Koloa, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,110 ($1,016/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 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

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,840 ($549/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)
2 bed/2 bath, sleeps 8
$5,257 ($751/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 Ko Olina Beach Club

Kapolei, Hawaii

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,358 ($623/night)

Verified & Protected

Marriott's Kauai Lagoons - Kalanipu'u

Lihue, Hawaii

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,712 ($673/night)