Winter Rentals
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,470 ($781/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,766 ($681/night)
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,949 ($564/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $3,606 ($515/night)
Verified & Protected
Hyatt Vacation Club at Sirena del Mar
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $9,944 ($1,421/night)
Verified & Protected
Garza Blanca Resort & Spa Los Cabos
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $22,915 ($3,274/night)
Verified & Protected
Villa La Estancia Cabo San Lucas
Cabo San Lucas, Mexico- Dec 19–26, 2026 (7 nights)
- 2 bed/3 bath, sleeps 3
- $8,200 ($1,171/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,968 ($424/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,213 ($1,888/night)
Verified & Protected
The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,562 ($1,366/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Dec 20–27, 2026 (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- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,545 ($1,078/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $25,203 ($1,800/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,564 ($938/night)
Verified & Protected
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $14,848 ($1,061/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- Studio/1 bath, sleeps 4
- $11,033 ($788/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,545 ($1,078/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $5,365 ($766/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,110 ($1,016/night)
Verified & Protected
Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,859 ($408/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,966 ($852/night)
Verified & Protected
Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 6
- $2,314 ($331/night)
Verified & Protected
Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,385 ($198/night)
Verified & Protected
Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
Verified & Protected
Grand Luxxe Spa Suites at Vidanta Nuevo Vallarta
Nuevo Vallarta, Mexico- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $9,834 ($1,405/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
La Cabana Beach Resort
Oranjestad, Aruba- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,382 ($1,055/night)
Verified & Protected
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $4,711 ($673/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $7,437 ($1,062/night)
Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($346/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $27,819 ($1,987/night)
Verified & Protected
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $24,005 ($3,429/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
La Cabana Beach Resort
Oranjestad, Aruba- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,459 ($351/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,375 ($1,482/night)
Verified & Protected
Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,712 ($673/night)
Verified & Protected
Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,384 ($626/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,458 ($494/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,403 ($486/night)