Winter Rentals
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,824 ($689/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 17–24, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,802 ($829/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,368 ($624/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,404 ($486/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,382 ($626/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 18–22, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($769/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 18–25, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,219 ($1,031/night)
Verified & Protected
Marriott's Kauai Lagoons - Kalanipu'u
Lihue, Hawaii- Jan 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,984 ($712/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,652 ($1,093/night)
Verified & Protected
Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 21–25, 2027 (4 nights)
- 1 bed/2 bath, sleeps 6
- $1,550 ($388/night)
Verified & Protected
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 22–29, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $9,018 ($1,288/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,289 ($1,327/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,598 ($657/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 22–29, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,859 ($408/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 22–29, 2027 (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- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 22–29, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,380 ($1,483/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,944 ($1,421/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 22–26, 2027 (4 nights)
- 2 bed/2.5 bath, sleeps 8
- $8,091 ($2,023/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Marriott's Summit Watch
Park City, Utah- Jan 22–25, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $1,878 ($626/night)
Verified & Protected
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Jan 22–29, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,022 ($432/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 22–29, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/night)
The Point at Poipu
Koloa, Hawaii- Jan 22–29, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,275 ($611/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 22–29, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,532 ($362/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,347 ($907/night)
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,977 ($711/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
Verified & Protected
Marriott's Summit Watch
Park City, Utah- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Grand Solmar Land's End Resort
Cabo San Lucas, Mexico- Jan 23–30, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $6,020 ($860/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,949 ($564/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 23–30, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,731 ($533/night)
Verified & Protected
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 23–30, 2027 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $10,380 ($1,483/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,147 ($735/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,083 ($1,012/night)
Verified & Protected
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,701 ($957/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 23–30, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,701 ($957/night)