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- Feb 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,535 ($505/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 2–14, 2027 (12 nights)
- 1 bed/1 bath, sleeps 4
- $7,546 ($629/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 4–18, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $6,053 ($432/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,800 ($971/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 5–12, 2027 (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- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,148 ($735/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 5–12, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,598 ($1,514/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,746 ($821/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,966 ($852/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,470 ($781/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 5–8, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,752 ($584/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 5–8, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,752 ($584/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,175 ($739/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 5–12, 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- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,328 ($761/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 5–12, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,351 ($764/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,069 ($438/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,560 ($937/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,268 ($467/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,298 ($614/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,069 ($581/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,001 ($1,000/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,006 ($1,001/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,505 ($358/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,271 ($610/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 3
- $2,917 ($417/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,451 ($493/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,358 ($765/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,053 ($865/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,733 ($533/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 6–13, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/night)