Winter Timeshare Rentals in Hawaii

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 14–21, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 14–24, 2026 (10 nights)
2 bed/3 bath, sleeps 8
$12,000 ($1,200/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,564 ($938/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 15–22, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,510 ($930/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 15–22, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 15–22, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 15–22, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,556 ($937/night)

Club Wyndham Kona Hawaiian Resort

Kailua-Kona, Hawaii

Dec 16–27, 2026 (11 nights)
2 bed/2 bath, sleeps 6
$5,366 ($488/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 16–23, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 16–23, 2026 (7 nights)
Studio/1 bath, sleeps 2
$3,513 ($502/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 16–21, 2026 (5 nights)
2 bed/3 bath, sleeps 8
$4,112 ($822/night)

Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 17–24, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,020 ($860/night)

Verified & Protected

Imperial Hawaii Vacation Club

Honolulu, Hawaii

Dec 18–25, 2026 (7 nights)
Studio/1 bath, sleeps 4
$1,099 ($157/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
$13,050 ($1,864/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 Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 18–26, 2026 (8 nights)
1 bed/2 bath, sleeps 4
$7,873 ($984/night)

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
$8,309 ($1,187/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
$5,801 ($829/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
$4,493 ($642/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$8,418 ($1,203/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,655 ($1,094/night)

Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

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

Verified & Protected

Hanalei Bay Resort

Princeville, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,211 ($602/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,382 ($1,055/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
$5,099 ($728/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
$8,582 ($1,226/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)

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
$7,219 ($1,031/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 Nanea Ocean Villas

Lahaina, Hawaii

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

Verified & Protected

Imperial Hawaii Vacation Club

Honolulu, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/1 bath, sleeps 6
$1,099 ($157/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

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

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$4,112 ($588/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 Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,272 ($1,039/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
$6,838 ($977/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 Voted Top Pick 2026

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$9,835 ($1,405/night)

Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 18–24, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$3,622 ($604/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 Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,763 ($1,109/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
$5,470 ($781/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

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 18–25, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$13,105 ($1,872/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,020 ($860/night)

Verified & Protected

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 19–26, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$8,745 ($1,249/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,931 ($847/night)

Verified & Protected

The Point at Poipu

Koloa, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,603 ($658/night)