Winter Timeshare Rentals in Oahu

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, 2026 – Jan 1, 2027 (10 nights)
2 bed/2 bath, sleeps 8
$10,914 ($1,091/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 22–29, 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, 2026 – Jan 2, 2027 (11 nights)
2 bed/2 bath, sleeps 8
$11,955 ($1,087/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 22–24, 2026 (2 nights)
Studio/1 bath, sleeps 4
$1,660 ($830/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 23–29, 2026 (6 nights)
Studio/1 bath, sleeps 4
$4,930 ($822/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 23, 2026 – Jan 2, 2027 (10 nights)
2 bed/2 bath, sleeps 8
$11,960 ($1,196/night)

Verified & Protected

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

Dec 23, 2026 – Jan 1, 2027 (9 nights)
1 bed/1 bath, sleeps 6
$4,538 ($504/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 23–26, 2026 (3 nights)
Studio/1 bath, sleeps 4
$3,458 ($1,153/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 23–27, 2026 (4 nights)
Studio/1 bath, sleeps 4
$3,578 ($895/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 24–31, 2026 (7 nights)
Studio/1 bath, sleeps 4
$6,121 ($874/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,938 ($848/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 24, 2026 – Jan 3, 2027 (10 nights)
2 bed/2 bath, sleeps 8
$16,375 ($1,638/night)

Verified & Protected

Imperial Hawaii Vacation Club

Honolulu, Hawaii

Dec 24–31, 2026 (7 nights)
Studio/1 bath, sleeps 4
$1,311 ($187/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$7,873 ($1,125/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$12,197 ($1,742/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,990 ($1,284/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,723 ($1,246/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,508 ($1,358/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,200 ($1,171/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$8,745 ($1,249/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,309 ($1,187/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,990 ($1,284/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$6,674 ($953/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,835 ($1,405/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 2
$4,058 ($580/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$5,584 ($798/night)

Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 5
$12,015 ($1,716/night)

Verified & Protected

The Grand Islander by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$7,617 ($1,088/night)

Verified & Protected

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 6
$3,840 ($549/night)

Verified & Protected

Kalia Suites by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,268 ($467/night)

Verified & Protected

Wyndham Vacation Resorts Royal Garden at Waikiki

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 2
$2,095 ($299/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,458 ($494/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (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 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$16,483 ($2,355/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,418 ($1,203/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$11,503 ($1,643/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$11,503 ($1,643/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26–31, 2026 (5 nights)
Studio/1 bath, sleeps 2
$3,076 ($615/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$11,906 ($1,701/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$10,326 ($1,475/night)

Verified & Protected

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$4,214 ($602/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,835 ($1,405/night)

Verified & Protected

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$7,274 ($1,039/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$10,925 ($1,561/night)

Verified & Protected

Imperial Hawaii Vacation Club

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/2 bath, sleeps 4
$1,434 ($205/night)

Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$4,603 ($658/night)