Winter Rentals
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 2–7, 2026 (5 nights)
- 3 bed/3.5 bath, sleeps 8
- $9,835 ($1,967/night)
Verified & Protected
Marriott Vacation Club, Waikiki
Honolulu, Hawaii- Dec 2–9, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,486 ($498/night)
Verified & Protected
Villa del Palmar Flamingos
Nuevo Vallarta, Mexico- Dec 3–10, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,314 ($331/night)
The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 3–7, 2026 (4 nights)
- 3 bed/3.5 bath, sleeps 8
- $7,873 ($1,968/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 3–10, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
Verified & Protected
Marriott Vacation Club at Los Sueños
Playa Jaco, Costa Rica- Dec 4–12, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $5,312 ($664/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 4–11, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,995 ($428/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 4–9, 2026 (5 nights)
- 2 bed/2 bath, sleeps 6
- $8,745 ($1,749/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,132 ($447/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,557 ($794/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 4–11, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 4–11, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,204 ($743/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 4–11, 2026 (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- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
Verified & Protected
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 5
- $5,205 ($744/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,557 ($794/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,407 ($630/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,204 ($315/night)
Verified & Protected
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,614 ($373/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Verified & Protected
Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $3,600 ($514/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,366 ($767/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 5–12, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,475 ($782/night)
Verified & Protected
La Cabana Beach Resort
Oranjestad, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,971 ($282/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,366 ($767/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Verified & Protected
La Cabana Beach Resort
Oranjestad, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,971 ($282/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,001 ($1,000/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,726 ($532/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,129 ($876/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,551 ($650/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,330 ($619/night)
Verified & Protected
Marriott's Phuket Beach Club
Phuket, Thailand- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Marriott's Phuket Beach Club
Phuket, Thailand- Dec 5–12, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)