Winter Timeshare Rentals in Hawaii

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
$5,358 ($765/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 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 Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,783 ($969/night)

Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,214 ($1,031/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
$5,693 ($813/night)

Verified & Protected

Club Wyndham Royal Sea Cliff

Kailua-Kona, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,295 ($471/night)

Verified & Protected

Grand Waikikian by Hilton Grand Vacations

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,638 ($806/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
$10,162 ($1,452/night)

Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,020 ($860/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

Marriott's Maui Ocean Club - Napili Tower

Lahaina, Hawaii

Dec 19, 2026 – Jan 2, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$13,105 ($936/night)

Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,118 ($874/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
$7,274 ($1,039/night)

Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,598 ($657/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
$8,146 ($1,164/night)

Verified & Protected

The Point at Poipu

Koloa, 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)
Studio/1 bath, sleeps 2
$3,948 ($564/night)

Verified & Protected

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 19–26, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$6,884 ($983/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 Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 19–26, 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 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,495 ($1,071/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 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

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

Imperial Hawaii Vacation Club

Honolulu, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$1,856 ($265/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 Ko Olina Beach Club

Kapolei, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$10,625 ($1,518/night)

Verified & Protected

The Point at Poipu

Koloa, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,077 ($440/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
$4,930 ($704/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

Westin Princeville Ocean Resort Villas

Princeville, 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, 2026 – Jan 2, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$15,067 ($1,076/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
$10,108 ($1,444/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
$10,100 ($1,443/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 Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 19, 2026 – Jan 2, 2027 (14 nights)
2 bed/2 bath, sleeps 8
$21,770 ($1,555/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)
2 bed/2 bath, sleeps 8
$6,346 ($907/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

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$3,922 ($560/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
$9,835 ($1,405/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

Marriott's Waikoloa Ocean Club

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$9,290 ($1,327/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 Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/2 bath, sleeps 4
$4,712 ($673/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
$8,091 ($1,156/night)

Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$4,167 ($595/night)