Winter Rentals
Verified & Protected
Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,726 ($532/night)
Verified & Protected
Garza Blanca Preserve Resort & Spa
Puerto Vallarta, Mexico- Dec 20–27, 2026 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $19,100 ($2,729/night)
Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,833 ($262/night)
Verified & Protected
Divi Village Golf and Beach Resort
Oranjestad, Aruba- Dec 20–27, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,902 ($414/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $8,745 ($1,249/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,004 ($572/night)
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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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)
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Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,213 ($745/night)
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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
- $4,058 ($580/night)
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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
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,750 ($393/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)
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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)
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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
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,292 ($899/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
- $6,292 ($899/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,562 ($1,366/night)
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,105 ($1,872/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
- $4,112 ($588/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 20–27, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,783 ($969/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)
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
Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
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Marriott's Summit Watch
Park City, Utah- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,199 ($1,171/night)
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
- $4,004 ($572/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,000 ($1,000/night)
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,020 ($860/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)
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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)
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Hyatt Vacation Club at Northstar Lodge
Truckee, California- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
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Hyatt Vacation Club at Northstar Lodge
Truckee, California- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,655 ($1,094/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21, 2026 – Jan 4, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $15,175 ($1,084/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,777 ($1,825/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,981 ($1,140/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 21–28, 2026 (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- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,617 ($1,088/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,404 ($486/night)
Verified & Protected
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 21–26, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,750 ($550/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $9,726 ($1,389/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21, 2026 – Jan 4, 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 21, 2026 – Jan 4, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $21,824 ($1,559/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 21–26, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($506/night)
Verified & Protected
The Club at Solaz, Los Cabos
San Jose del Cabo, Mexico- Dec 21–28, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,384 ($626/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 21–28, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $21,933 ($3,133/night)
Verified & Protected
Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 21–28, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)