Winter Rentals | RedWeek

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 Voted Top Pick 2025

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 19–26, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$4,385 ($626/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)

Voted #1 Resort 2025

Marriott's Aruba Surf Club

Palm Beach, Aruba

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$9,835 ($1,405/night)

Verified & Protected

Westgate Flamingo Bay

Las Vegas, Nevada

Dec 19–26, 2025 (7 nights)
4 bed/4 bath, sleeps 16
$3,316 ($474/night)

Verified & Protected Voted Top Pick 2025

Marriott's OceanWatch Villas at Grande Dunes

Myrtle Beach, South Carolina

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$4,603 ($658/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

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

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 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

Sheraton Vistana Resort

Orlando, Florida

Dec 19–24, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$555 ($111/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)

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

WorldMark Moab

Moab, Utah

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,922 ($275/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 Summit Watch

Park City, Utah

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$4,984 ($712/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 Bend - Seventh Mountain Resort

Bend, Oregon

Dec 19–26, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,110 ($159/night)

Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,290 ($470/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

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

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

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$8,745 ($1,249/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

Sheraton Desert Oasis

Scottsdale, Arizona

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,220 ($174/night)

Verified & Protected Voted Top Pick 2025

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$4,984 ($712/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

Marriott Grand Residence Club - Lake Tahoe

South Lake Tahoe, California

Dec 19–26, 2025 (7 nights)
2 bed/3 bath, sleeps 8
$4,603 ($658/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 Steamboat Resort Villas

Steamboat Springs, Colorado

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$5,366 ($767/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

Sheraton Vistana Resort

Orlando, Florida

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$888 ($127/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)

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

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 19–22, 2025 (3 nights)
2 bed/2 bath, sleeps 8
$502 ($167/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

Sheraton Kauai Resort Villas

Koloa, Hawaii

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$4,984 ($712/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

Westgate Smoky Mountain Resort & Water Park

Gatlinburg, Tennessee

Dec 19–26, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$777 ($111/night)

Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,220 ($174/night)

Verified & Protected Voted Top Pick 2025

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 19–23, 2025 (4 nights)
1 bed/1 bath, sleeps 4
$1,330 ($332/night)

Verified & Protected

Westgate Smoky Mountain Resort & Water Park

Gatlinburg, Tennessee

Dec 19–26, 2025 (7 nights)
3 bed/3 bath, sleeps 12
$3,240 ($463/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 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 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

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 Ritz-Carlton Club, St. Thomas

East End, St. Thomas (USVI)

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$11,470 ($1,639/night)