Winter Rentals
Verified & Protected
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–27, 2025 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,987 ($248/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
Verified & Protected
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2025
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
Verified & Protected
The Westin Mission Hills Villas
Rancho Mirage, California- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
Verified & Protected
The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Dec 19–26, 2025 (7 nights)
- 2 bed/3 bath, sleeps 6
- $5,693 ($813/night)
Verified & Protected
Marriott Grand Residence Club - Lake Tahoe
South Lake Tahoe, California- Dec 19–26, 2025 (7 nights)
- 2 bed/3 bath, sleeps 8
- $6,674 ($953/night)
Verified & Protected
Aquamarine Villas
Oceanside, California- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $777 ($111/night)
Verified & Protected
Sheraton Vistana Resort
Orlando, Florida- Dec 19–24, 2025 (5 nights)
- 2 bed/2 bath, sleeps 8
- $555 ($111/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Newport Coast Villas
Newport Coast, California- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,723 ($389/night)
Verified & Protected
Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($412/night)
Verified & Protected
Woodstone at Massanutten & Woodstone Casas
McGaheysville, Virginia- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,987 ($284/night)
Verified & Protected
Coconut Mallory Marina & Resort
Key West, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,742 ($249/night)
Verified & Protected
Eagle Point Resort
Vail, Colorado- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($268/night)
Verified & Protected
Hyatt Pinon Pointe
Sedona, Arizona- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($237/night)
Verified & Protected
Kahana Villa Resort
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,532 ($362/night)
Verified & Protected
Voted Top Pick 2025
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,042 ($292/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $18,991 ($2,713/night)
Verified & Protected
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 19–26, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $3,022 ($432/night)
Verified & Protected
The Westin St. John - Sunset Bay Villas
Cruz Bay, St. John (USVI)- Dec 19–26, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $3,649 ($521/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,475 ($782/night)
Verified & Protected
Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Woodstone at Massanutten & Woodstone Casas
McGaheysville, Virginia- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,396 ($199/night)
Verified & Protected
WorldMark Steamboat Springs Resort
Steamboat Springs, Colorado- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,560 ($937/night)
Verified & Protected
Voted #1 Resort 2025
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 19–26, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $3,294 ($471/night)
Verified & Protected
Kings' Land by Hilton Grand Vacations
Waikoloa Village, Hawaii- Dec 19–27, 2025 (8 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($303/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $686,725 ($98,104/night)
Verified & Protected
Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Dec 19–27, 2025 (8 nights)
- 3 bed/3.5 bath, sleeps 10
- $3,077 ($385/night)
Verified & Protected
Morritt's Grand Resort
East End, Grand Cayman, Cayman Islands- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,859 ($408/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Crystal Shores
Marco Island, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,167 ($595/night)
Verified & Protected
Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Crystal Shores
Marco Island, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,200 ($1,171/night)
Verified & Protected
Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
Verified & Protected
Westgate Smoky Mountain Resort & Water Park
Gatlinburg, Tennessee- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,660 ($237/night)
Verified & Protected
Voted #1 Resort 2025
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $14,195 ($2,028/night)
Verified & Protected
Voted Top Pick 2025
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,966 ($852/night)
Verified & Protected
Voted Top Pick 2025
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,042 ($292/night)
Verified & Protected
Marriott's Grande Vista
Orlando, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($237/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 19–21, 2025 (2 nights)
- 3 bed/3.5 bath, sleeps 8
- $3,186 ($1,593/night)
Verified & Protected
The Summit at Massanutten
McGaheysville, Virginia- Dec 19–26, 2025 (7 nights)
- 4 bed/4 bath, sleeps 12
- $1,330 ($190/night)
Verified & Protected
Voted Top Pick 2025
Marriott's MountainSide at Park City
Park City, Utah- Dec 19–21, 2025 (2 nights)
- 2 bed/2 bath, sleeps 8
- $1,110 ($555/night)
Verified & Protected
Marriott's Willow Ridge Lodge
Branson, Missouri- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($190/night)
Verified & Protected
Voted Top Pick 2025
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,493 ($642/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,240 ($463/night)