Winter Rentals
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 13–20, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 13–20, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
Verified & Protected
Disney's Riviera Resort
Lake Buena Vista, Florida- Dec 13–18, 2026 (5 nights)
- Studio/1 bath, sleeps 5
- $2,619 ($524/night)
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,038 ($720/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Marriott's Phuket Beach Club
Phuket, Thailand- Dec 13–20, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,112 ($588/night)
Verified & Protected
Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 13–19, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($640/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 13–20, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,095 ($299/night)
Verified & Protected
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 13–18, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,510 ($502/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,380 ($626/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,493 ($642/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $6,510 ($930/night)
Verified & Protected
Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Dec 14–20, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $2,170 ($362/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 14–19, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,156 ($431/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,275 ($611/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 14–20, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $4,865 ($811/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 14–20, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $2,641 ($440/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 14–21, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 14–21, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,404 ($486/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 14–21, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,204 ($315/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,564 ($938/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 15–22, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,347 ($907/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 15–22, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Disney's Riviera Resort
Lake Buena Vista, Florida- Dec 15–17, 2026 (2 nights)
- Studio/1 bath, sleeps 5
- $981 ($491/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 15–20, 2026 (5 nights)
- Studio/1 bath, sleeps 5
- $2,706 ($541/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 15–22, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Dec 16, 2026 – Jan 2, 2027 (17 nights)
- 3 bed/3.5 bath, sleeps 10
- $9,290 ($546/night)
Verified & Protected
Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Dec 16, 2026 – Jan 2, 2027 (17 nights)
- 3 bed/3.5 bath, sleeps 10
- $8,745 ($514/night)
Verified & Protected
Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 17–24, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($415/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 17–24, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,314 ($331/night)
Verified & Protected
Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 17–24, 2026 (7 nights)
- Studio/1 bath, sleeps 5
- $4,498 ($643/night)
Verified & Protected
Club Ocho Cascadas
Puerto Vallarta, Mexico- Dec 17–24, 2026 (7 nights)
- 3 bed/3 bath, sleeps 8
- $3,077 ($440/night)
Verified & Protected
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 17–20, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $1,554 ($518/night)
Verified & Protected
Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 17–21, 2026 (4 nights)
- Studio/1 bath, sleeps 5
- $2,615 ($654/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,399 ($1,343/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 18–24, 2026 (6 nights)
- Studio/1 bath, sleeps 5
- $3,871 ($645/night)
Verified & Protected
Imperial Hawaii Vacation Club
Honolulu, Hawaii- Dec 18–25, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,280 ($183/night)
Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,707 ($1,530/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,582 ($1,226/night)
Verified & Protected
Westgate Town Center
Kissimmee, Florida- Dec 18–25, 2026 (7 nights)
- 4 bed/4 bath, sleeps 16
- $2,257 ($322/night)
Verified & Protected
Four Seasons Residence Club Aviara
Carlsbad, California- Dec 18, 2026 – Jan 1, 2027 (14 nights)
- 2 bed/3 bath, sleeps 8
- $8,745 ($625/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 18–25, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,853 ($1,265/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 18–26, 2026 (8 nights)
- 1 bed/2 bath, sleeps 4
- $7,873 ($984/night)