Winter Timeshare Rentals in Hawaii

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$7,655 ($1,094/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,564 ($938/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,560 ($937/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$6,946 ($992/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$13,660 ($1,951/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,214 ($602/night)

Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

Dec 18–23, 2026 (5 nights)
2 bed/2 bath, sleeps 6
$2,179 ($436/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$7,274 ($1,039/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,473 ($782/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,396 ($914/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$2,968 ($424/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,674 ($953/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,434 ($919/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,058 ($580/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,963 ($423/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,887 ($984/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$8,036 ($1,148/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,434 ($919/night)

Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 18–23, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$4,325 ($865/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,047 ($292/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,022 ($432/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$9,726 ($1,389/night)

Verified & Protected

Kona Coast Resort

Kailua-Kona, Hawaii

Dec 18–26, 2026 (8 nights)
2 bed/2 bath, sleeps 6
$2,859 ($357/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,112 ($588/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$5,038 ($720/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,510 ($930/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,121 ($1,017/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,510 ($930/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,464 ($1,066/night)

Verified & Protected

The Cliffs at Princeville

Princeville, Hawaii

Dec 18–25, 2026 (7 nights)
4 bed/4 bath, sleeps 12
$7,655 ($1,094/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,894 ($556/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$8,745 ($1,249/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$8,740 ($1,249/night)

Sands of Kahana Vacation Club

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$3,153 ($450/night)

Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$10,707 ($1,530/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,838 ($977/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$9,181 ($1,312/night)

Verified & Protected

The Cliffs at Princeville

Princeville, Hawaii

Dec 18, 2026 – Jan 1, 2027 (14 nights)
1 bed/2 bath, sleeps 8
$7,655 ($547/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$9,617 ($1,374/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 18–28, 2026 (10 nights)
1 bed/1 bath, sleeps 4
$8,199 ($820/night)

Verified & Protected Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,647 ($1,092/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$5,786 ($827/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 18–25, 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 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,984 ($712/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
Studio/1 bath, sleeps 4
$4,222 ($603/night)

Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,129 ($876/night)