Winter Rentals
Verified & Protected
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 24–31, 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 24–31, 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 24–31, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 24–31, 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 25 – Feb 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 25 – Feb 1, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $9,507 ($1,358/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 25 – Feb 2, 2027 (8 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($344/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 26 – Feb 1, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,186 ($531/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 26 – Feb 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,129 ($876/night)
Verified & Protected
The Grand Islander by Hilton Grand Vacations
Honolulu, Hawaii- Jan 29 – Feb 5, 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 29 – Feb 5, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $12,560 ($1,794/night)
The Point at Poipu
Koloa, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,275 ($611/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,673 ($953/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 29 – Feb 5, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,676 ($525/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 29 – Feb 5, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 29 – Feb 5, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,948 ($564/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 29 – Feb 5, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,730 ($533/night)
Verified & Protected
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 29 – Feb 5, 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 29 – Feb 5, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $8,962 ($1,280/night)
Verified & Protected
WorldMark Scottsdale
Scottsdale, Arizona- Jan 30 – Feb 13, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $3,825 ($273/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,365 ($766/night)
Verified & Protected
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
Verified & Protected
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,783 ($969/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $12,668 ($1,810/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,622 ($517/night)
Verified & Protected
Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,748 ($821/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,257 ($751/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,202 ($743/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,603 ($658/night)
Verified & Protected
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 3 bed/2.5 bath, sleeps 8
- $10,380 ($1,483/night)
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,833 ($405/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,328 ($1,047/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
Verified & Protected
The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 30 – Feb 6, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,200 ($1,171/night)
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,276 ($611/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,949 ($564/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($735/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,650 ($1,093/night)