Winter Timeshare Rentals in Oahu

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,114 ($873/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 4
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,347 ($907/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,200 ($1,171/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,726 ($1,389/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,644 ($1,092/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,655 ($1,094/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,039 ($720/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,862 ($837/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,748 ($821/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 2
$4,222 ($603/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 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 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,556 ($1,079/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$6,456 ($922/night)

Verified & Protected

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,214 ($602/night)

Verified & Protected

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,358 ($765/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
$8,091 ($1,156/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
$7,437 ($1,062/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
$7,846 ($1,121/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 20–26, 2026 (6 nights)
Studio/1 bath, sleeps 4
$5,420 ($903/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

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$6,347 ($907/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,984 ($712/night)

Verified & Protected

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 20–23, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$1,824 ($608/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–23, 2026 (3 nights)
Studio/1 bath, sleeps 2
$1,032 ($344/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,366 ($767/night)

Verified & Protected

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

Dec 20–23, 2026 (3 nights)
1 bed/1 bath, sleeps 6
$1,660 ($553/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
$7,274 ($1,039/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
$8,522 ($1,217/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
$7,650 ($1,093/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
$12,451 ($1,779/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
$7,274 ($1,039/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

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 Ko Olina Beach Club

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$10,707 ($1,530/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
$6,884 ($983/night)

Verified & Protected

Club Wyndham at Waikiki Beach Walk

Honolulu, Hawaii

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,061 ($723/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
$7,853 ($1,122/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
Studio/1 bath, sleeps 4
$6,587 ($941/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 5
$12,386 ($1,769/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
$8,413 ($1,202/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20, 2026 – Jan 3, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$15,285 ($1,092/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 20, 2026 – Jan 1, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$10,489 ($874/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
$6,701 ($957/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 21–26, 2026 (5 nights)
1 bed/1 bath, sleeps 5
$10,707 ($2,141/night)