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)
3 bed/3 bath, sleeps 10
$10,380 ($1,483/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
$6,346 ($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
$6,783 ($969/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

Imperial Hawaii Vacation Club

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$1,856 ($265/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
$4,603 ($658/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
$7,432 ($1,062/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 Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,385 ($626/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
$5,911 ($844/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
$10,380 ($1,483/night)

Verified & Protected

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

Dec 19–26, 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 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,252 ($750/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
$6,346 ($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
$7,495 ($1,071/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)
Studio/1 bath, sleeps 2
$4,167 ($595/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
$8,987 ($1,284/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
$16,915 ($2,416/night)

Verified & Protected

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$10,380 ($1,483/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
$6,216 ($888/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
$8,200 ($1,171/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

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

Dec 20–23, 2026 (3 nights)
1 bed/1 bath, sleeps 6
$1,660 ($553/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)
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
$8,304 ($1,186/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
$8,199 ($1,171/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

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

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 5
$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)
1 bed/1 bath, sleeps 4
$5,366 ($767/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 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,265 ($895/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

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)
2 bed/2 bath, sleeps 8
$7,853 ($1,122/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

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)
2 bed/2 bath, sleeps 8
$6,129 ($876/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 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 21–28, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,366 ($767/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 22–29, 2026 (7 nights)
Studio/1 bath, sleeps 2
$3,731 ($533/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 22, 2026 – Jan 1, 2027 (10 nights)
2 bed/2 bath, sleeps 8
$11,742 ($1,174/night)