Winter Timeshare Rentals
Winter getaways are always popular, making now the perfect time to secure exclusive timeshare deals for your seasonal escape! Whether you're dreaming of a snowy mountain retreat or a warm-weather getaway, these timeshare rentals offer the perfect setting to make your winter vacation unforgettable.
Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,676 ($525/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
One Napili Way
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/2 bath, sleeps 6
- $1,932 ($276/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,832 ($547/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,268 ($467/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,480 ($783/night)
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,451 ($493/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,458 ($494/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,848 ($407/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Ocean Tower by Hilton Grand Vacations Club
Waikoloa Village, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $4,930 ($704/night)
Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,031 ($576/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,894 ($271/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,252 ($750/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,240 ($463/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,800 ($829/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,802 ($543/night)
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
The Point at Poipu
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,687 ($527/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,069 ($438/night)
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Pono Kai
Kapaa, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,588 ($227/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,123 ($303/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $2,505 ($358/night)
Maui Bay Villas by Hilton Grand Vacations
Kihei, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,745 ($1,249/night)
Maui Schooner
Kihei, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $1,932 ($276/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,123 ($303/night)
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,984 ($712/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Sheraton Kauai Resort Villas
Koloa, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,183 ($598/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,925 ($1,561/night)
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $2,696 ($385/night)
Kauai Beach Villas
Lihue, Hawaii- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $2,314 ($331/night)
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,374 ($625/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($346/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,603 ($658/night)
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)