Winter Timeshare Rentals in Hawaii

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$6,238 ($891/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,690 ($1,242/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 Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$11,796 ($1,685/night)

Verified & Protected

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,276 ($611/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 Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,840 ($549/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

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,925 ($704/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$6,129 ($876/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas North

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,830 ($1,404/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
$8,418 ($1,203/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,584 ($798/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
$6,510 ($930/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)
2 bed/2 bath, sleeps 6
$5,748 ($821/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
$6,946 ($992/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
$5,366 ($767/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
$5,039 ($720/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$11,033 ($1,576/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,290 ($1,327/night)

Verified & Protected

Hokulani Waikiki by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,385 ($626/night)

Verified & Protected

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$18,118 ($2,588/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

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$8,036 ($1,148/night)

Verified & Protected

Kahana Villa Resort

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,930 ($704/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,532 ($362/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
$6,455 ($922/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
$3,840 ($549/night)

Verified & Protected

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$10,380 ($1,483/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$10,291 ($1,470/night)

Verified & Protected

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$14,195 ($2,028/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,268 ($467/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
$5,354 ($765/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$6,227 ($890/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
$6,620 ($946/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$10,707 ($1,530/night)

Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$10,925 ($1,561/night)

Verified & Protected

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$9,398 ($1,343/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
$5,366 ($767/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

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$5,540 ($791/night)

Verified & Protected

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$6,129 ($876/night)

Verified & Protected

Sands of Kahana Vacation Club

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
3 bed/2 bath, sleeps 8
$4,167 ($595/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$7,056 ($1,008/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

Pono Kai

Kapaa, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,204 ($315/night)