Winter Timeshare Rentals in Hawaii

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$9,835 ($1,405/night)

Verified & Protected

Marriott's Kauai Lagoons - Kalanipu'u

Lihue, Hawaii

Dec 26, 2026 – Jan 1, 2027 (6 nights)
3 bed/3 bath, sleeps 8
$5,474 ($912/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

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

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$7,655 ($1,094/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,840 ($549/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
$8,745 ($1,249/night)

Verified & Protected

Imperial Hawaii Vacation Club

Honolulu, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/2 bath, sleeps 4
$1,856 ($265/night)

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Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$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)
1 bed/1 bath, sleeps 4
$4,603 ($658/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,290 ($1,327/night)

Verified & Protected

Marriott's Kauai Lagoons - Kalanipu'u

Lihue, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$5,769 ($824/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
$3,721 ($532/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$10,042 ($1,435/night)

Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$5,470 ($781/night)

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Hanalei Bay Resort

Princeville, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$7,192 ($1,027/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,510 ($930/night)

Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,968 ($424/night)

Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$4,636 ($662/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
$3,786 ($541/night)

Verified & Protected

Maui Bay Villas by Hilton Grand Vacations

Kihei, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,830 ($1,404/night)

Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,749 ($393/night)

Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,749 ($393/night)

Verified & Protected

Sands of Kahana Vacation Club

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,478 ($354/night)

Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,949 ($564/night)

Verified & Protected Voted Top Pick 2026

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,740 ($1,249/night)

Verified & Protected

Kings' Land by Hilton Grand Vacations

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,749 ($393/night)

Verified & Protected

Pono Kai

Kapaa, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,532 ($362/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
$10,161 ($1,452/night)

Verified & Protected

Pono Kai

Kapaa, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,532 ($362/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 3
$2,750 ($393/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
$10,379 ($1,483/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/2 bath, sleeps 4
$3,730 ($533/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/2 bath, sleeps 4
$4,276 ($611/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,200 ($1,171/night)

Verified & Protected

Club Wyndham Ka 'Eo Kai

Princeville, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,839 ($548/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,018 ($1,288/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$13,213 ($1,888/night)

Verified & Protected

Ocean Tower by Hilton Grand Vacations Club

Waikoloa Village, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$6,565 ($938/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

Dec 26, 2026 – Jan 1, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$4,930 ($822/night)

Verified & Protected Voted Top Pick 2026

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$10,053 ($1,436/night)

Verified & Protected

The Point at Poipu

Koloa, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$4,222 ($603/night)

Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$7,545 ($1,078/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

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

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/2 bath, sleeps 4
$4,821 ($689/night)

Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$6,701 ($957/night)

Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/3 bath, sleeps 8
$10,380 ($1,483/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)