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.
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Club Wyndham Mauna Loa Village
Kailua-Kona, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $2,276 ($325/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–11, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($833/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–11, 2026 (5 nights)
- 3 bed/3 bath, sleeps 10
- $5,475 ($1,095/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,579 ($797/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,361 ($766/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 6–13, 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 6–13, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,617 ($1,374/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 6–10, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $2,327 ($582/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,458 ($494/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $4,788 ($684/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,938 ($848/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,807 ($544/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,486 ($498/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Paniolo Greens
Waikoloa Village, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,704 ($243/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,999 ($428/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,969 ($853/night)
Verified & Protected
Kahana Beach Resort
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,314 ($331/night)
Verified & Protected
Hanalei Bay Resort
Princeville, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,358 ($623/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,204 ($315/night)
Verified & Protected
Sands of Kahana Vacation Club
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,557 ($794/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 6–12, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($549/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,448 ($493/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 6–13, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,336 ($619/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 6–12, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($495/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 7–21, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $15,575 ($1,112/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,938 ($848/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 7–14, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,282 ($897/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,494 ($642/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 8–15, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 9–19, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($820/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 9–16, 2026 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,246 ($1,321/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Dec 9–15, 2026 (6 nights)
- 3 bed/3 bath, sleeps 8
- $5,748 ($958/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 9–13, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $1,769 ($442/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 9–19, 2026 (10 nights)
- Studio/1 bath, sleeps 2
- $2,941 ($294/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)