Winter Timeshare Rentals in Hawaii

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
$4,603 ($658/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
$4,358 ($623/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 7–14, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,938 ($848/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 7–14, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,513 ($502/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 7–21, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$15,728 ($1,123/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
$4,494 ($642/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
$5,257 ($751/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
$4,167 ($595/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 8–15, 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 9–19, 2026 (10 nights)
2 bed/2 bath, sleeps 8
$8,200 ($820/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)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 9–19, 2026 (10 nights)
Studio/1 bath, sleeps 2
$3,295 ($330/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

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,622 ($517/night)

Verified & Protected

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

Dec 10–17, 2026 (7 nights)
1 bed/1 bath, sleeps 6
$3,186 ($455/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 Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,748 ($821/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

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 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,440 ($634/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 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

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

Club Wyndham at Waikiki Beach Walk

Honolulu, Hawaii

Dec 11–15, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$2,527 ($632/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)
2 bed/2 bath, sleeps 6
$8,058 ($1,151/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)
2 bed/2 bath, sleeps 6
$4,494 ($642/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 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)
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 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,222 ($603/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,557 ($794/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,347 ($907/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
$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)
2 bed/2 bath, sleeps 8
$6,129 ($876/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 Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 11–16, 2026 (5 nights)
Studio/1 bath, sleeps 4
$2,096 ($419/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,001 ($429/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 11–18, 2026 (7 nights)
Studio/1 bath, sleeps 2
$1,932 ($276/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/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)