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.
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,320 ($903/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,061 ($723/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,892 ($985/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,568 ($510/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,505 ($358/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–8, 2027 (5 nights)
- Studio/1 bath, sleeps 2
- $3,076 ($615/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,696 ($385/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,306 ($329/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 3–8, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $3,568 ($714/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,153 ($450/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,512 ($502/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,564 ($938/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,306 ($472/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,058 ($580/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,053 ($865/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,824 ($689/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 3–10, 2027 (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- Jan 3–11, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $5,859 ($732/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,145 ($592/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($938/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 4–10, 2027 (6 nights)
- 3 bed/2 bath, sleeps 8
- $8,690 ($1,448/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 4–11, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 5–16, 2027 (11 nights)
- 2 bed/3 bath, sleeps 8
- $11,470 ($1,043/night)
Verified & Protected
Kohala Suites by Hilton Grand Vacations
Waikoloa Village, Hawaii- Jan 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,034 ($719/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 5–12, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,967 ($424/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 5–19, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $11,470 ($819/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
The Gardens at West Maui
Kapalua, Hawaii- Jan 6–13, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,330 ($190/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 6–13, 2027 (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- Jan 6–10, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $3,426 ($856/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 7–12, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($581/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 7–16, 2027 (9 nights)
- 2 bed/2 bath, sleeps 6
- $4,341 ($482/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 8–15, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,001 ($429/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 8–15, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,903 ($700/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 8–14, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,519 ($420/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 8–14, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $2,903 ($484/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 8–15, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)