Winter Rentals
Verified & Protected
Hurricane House
Sanibel Island, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,204 ($315/night)
Verified & Protected
Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Dec 19–26, 2025 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $2,750 ($393/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
Marriott's SurfWatch
Hilton Head Island, South Carolina- Dec 19–27, 2025 (8 nights)
- 2 bed/2 bath, sleeps 8
- $888 ($111/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 Ocean Pointe
Palm Beach Shores, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,535 ($362/night)
Verified & Protected
Lawai Beach Resort
Koloa, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,240 ($463/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
- $4,450 ($636/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
- $2,749 ($393/night)
Verified & Protected
WorldMark West Yellowstone
West Yellowstone, Montana- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,922 ($275/night)
Verified & Protected
Marriott's Desert Springs Villas
Palm Desert, California- Dec 19–26, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $1,165 ($166/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
Voted Top Pick 2025
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 19–27, 2025 (8 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($385/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
- $9,072 ($1,296/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
Harborside Resort at Atlantis
Paradise Island, Bahamas- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($564/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
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
Marriott's Summit Watch
Park City, Utah- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,731 ($533/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 19–27, 2025 (8 nights)
- 4 bed/4 bath, sleeps 10
- $19,644 ($2,455/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
Voted Top Pick 2025
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Dec 19, 2025 – Jan 2, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $17,465 ($1,248/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
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 Top Pick 2025
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Dec 19–26, 2025 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,493 ($642/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)
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
Villa del Palmar Flamingos
Nuevo Vallarta, Mexico- Dec 19–26, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,660 ($237/night)
Verified & Protected
Voted Top Pick 2025
Marriott's MountainSide at Park City
Park City, Utah- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/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
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
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
Marriott's Shadow Ridge - The Villages
Palm Desert, California- Dec 19–26, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $555 ($79/night)
Verified & Protected
Voted Top Pick 2025
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 19–27, 2025 (8 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($276/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
- $9,105 ($1,301/night)
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Dec 19–26, 2025 (7 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($237/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
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
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 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
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
Marriott's Grande Vista
Orlando, Florida- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($237/night)
Verified & Protected
Villa del Palmar Flamingos
Nuevo Vallarta, Mexico- Dec 19–26, 2025 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,660 ($237/night)
Verified & Protected
Marriott's Kauai Beach Club
Lihue, Hawaii- Dec 19–26, 2025 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,384 ($626/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)
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)