Winter Timeshare Rentals in Hawaii

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,693 ($813/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,655 ($1,094/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,745 ($1,249/night)

Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,382 ($1,055/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 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 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,110 ($1,016/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,930 ($704/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,464 ($1,066/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,873 ($1,125/night)

Marriott's Kauai Lagoons - Kalanipu'u

Lihue, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,110 ($1,016/night)

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Marriott Vacation Club, Waikiki

Honolulu, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 6
$5,470 ($781/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$11,432 ($1,633/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,464 ($1,066/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,181 ($1,312/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$4,603 ($658/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$4,494 ($642/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$4,004 ($572/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,655 ($1,094/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$4,222 ($603/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,325 ($904/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,292 ($899/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 5
$14,307 ($2,044/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$6,238 ($891/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,966 ($852/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$7,546 ($1,078/night)

Verified & Protected

Imperial Hawaii Vacation Club

Honolulu, Hawaii

Dec 20–27, 2026 (7 nights)
Studio/1 bath, sleeps 4
$1,385 ($198/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,001 ($1,000/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,001 ($1,000/night)

Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,290 ($1,327/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$4,058 ($580/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,001 ($1,000/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$8,745 ($1,249/night)

The Point at Poipu

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,622 ($517/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,072 ($1,296/night)

Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$11,905 ($1,701/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/3 bath, sleeps 8
$8,418 ($1,203/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,403 ($486/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,510 ($930/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 20–27, 2026 (7 nights)
Studio/1 bath, sleeps 4
$2,750 ($393/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,237 ($891/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,292 ($899/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$13,650 ($1,950/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,067 ($1,010/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,458 ($494/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,382 ($1,055/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 21–28, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,641 ($377/night)