Winter Rentals | RedWeek

Verified & Protected Voted Top Pick 2025

Marriott's MountainSide at Park City

Park City, Utah

Dec 14–19, 2025 (5 nights)
Studio/1 bath, sleeps 4
$540 ($108/night)

Verified & Protected Voted Top Pick 2025

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 14–21, 2025 (7 nights)
1 bed/2 bath, sleeps 4
$2,205 ($315/night)

Verified & Protected

Marriott's St. Kitts Beach Club

Frigate Bay, St. Kitts

Dec 14–21, 2025 (7 nights)
3 bed/3 bath, sleeps 10
$2,750 ($393/night)

Verified & Protected

Westin Princeville Ocean Resort Villas

Princeville, Hawaii

Dec 14–21, 2025 (7 nights)
Studio/1 bath, sleeps 4
$944 ($135/night)

Verified & Protected

The Ritz-Carlton Club, Lake Tahoe

Truckee, California

Dec 14–19, 2025 (5 nights)
3 bed/3.5 bath, sleeps 8
$5,475 ($1,095/night)

Verified & Protected Voted Top Pick 2025

Marriott's Frenchman's Cove

Southside, St. Thomas (USVI)

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,295 ($471/night)

Verified & Protected

Branson's Nantucket

Branson, Missouri

Dec 14–21, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$738 ($105/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,110 ($159/night)

Verified & Protected

Marriott's Timber Lodge Tahoe

South Lake Tahoe, California

Dec 14–19, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$971 ($194/night)

Verified & Protected Voted Top Pick 2025

Marriott's Frenchman's Cove

Southside, St. Thomas (USVI)

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,649 ($236/night)

Westgate Lakes Resort & Spa

Orlando, Florida

Dec 14–21, 2025 (7 nights)
3 bed/3 bath, sleeps 12
$2,205 ($315/night)

Verified & Protected

Club Wyndham Panama City Beach

Panama City Beach, Florida

Dec 14–20, 2025 (6 nights)
2 bed/2 bath, sleeps 6
$777 ($130/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 14–16, 2025 (2 nights)
3 bed/3 bath, sleeps 10
$977 ($488/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 14–21, 2025 (7 nights)
3 bed/3 bath, sleeps 10
$3,622 ($517/night)

Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

Dec 14–19, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$1,110 ($222/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 14–21, 2025 (7 nights)
3 bed/3 bath, sleeps 12
$1,550 ($221/night)

Verified & Protected Voted Top Pick 2025

Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers

Lahaina, Hawaii

Dec 14–20, 2025 (6 nights)
Studio/1 bath, sleeps 4
$1,660 ($277/night)

Verified & Protected

Marriott's Royal Palms

Orlando, Florida

Dec 14–19, 2025 (5 nights)
2 bed/2 bath, sleeps 6
$405 ($81/night)

Verified & Protected Voted Top Pick 2025

Marriott's OceanWatch Villas at Grande Dunes

Myrtle Beach, South Carolina

Dec 14–20, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$777 ($130/night)

Verified & Protected

Marriott's Summit Watch

Park City, Utah

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$4,384 ($626/night)

Verified & Protected

Branson's Nantucket

Branson, Missouri

Dec 14–18, 2025 (4 nights)
3 bed/3.5 bath, sleeps 8
$1,061 ($265/night)

Verified & Protected Voted Top Pick 2025

The Westin Nanea Ocean Villas

Lahaina, Hawaii

Dec 14–18, 2025 (4 nights)
2 bed/2 bath, sleeps 6
$1,660 ($415/night)

Verified & Protected

Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 14–20, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$832 ($139/night)

Verified & Protected

Hilton Grand Vacations at MarBrisa

Carlsbad, California

Dec 14–21, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,110 ($159/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–17, 2025 (3 nights)
2 bed/2 bath, sleeps 8
$336 ($112/night)

Verified & Protected

Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen

Vail, Colorado

Dec 14–21, 2025 (7 nights)
1 bed/1 bath, sleeps 6
$1,110 ($159/night)

Verified & Protected Voted Top Pick 2025

Marriott's Newport Coast Villas

Newport Coast, California

Dec 14–19, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$1,385 ($277/night)

Verified & Protected

Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen

Vail, Colorado

Dec 14–18, 2025 (4 nights)
2 bed/2 bath, sleeps 8
$635 ($159/night)

Verified & Protected

Marriott's Grand Chateau

Las Vegas, Nevada

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$832 ($119/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,968 ($424/night)

Verified & Protected

Wyndham Vacation Resorts Steamboat Springs

Steamboat Springs, Colorado

Dec 14–18, 2025 (4 nights)
1 bed/1 bath, sleeps 4
$1,220 ($305/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 14–20, 2025 (6 nights)
1 bed/1 bath, sleeps 4
$484 ($81/night)

Verified & Protected Voted Top Pick 2025

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

Dec 14–19, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$435 ($87/night)

Verified & Protected

Marriott's Summit Watch

Park City, Utah

Dec 14–19, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$1,104 ($221/night)

Verified & Protected

Hyatt Pinon Pointe

Sedona, Arizona

Dec 14–20, 2025 (6 nights)
2 bed/2 bath, sleeps 6
$1,456 ($243/night)

Verified & Protected

The Westin St. John - Virgin Grand Villas

Cruz Bay, St. John (USVI)

Dec 14–21, 2025 (7 nights)
3 bed/3 bath, sleeps 8
$5,470 ($781/night)

Verified & Protected

Branson's Nantucket

Branson, Missouri

Dec 14–18, 2025 (4 nights)
3 bed/3.5 bath, sleeps 8
$1,066 ($266/night)

Verified & Protected

Grand Timber Lodge

Breckenridge, Colorado

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,750 ($393/night)

Verified & Protected Voted Top Pick 2025

Marriott's MountainSide at Park City

Park City, Utah

Dec 14–19, 2025 (5 nights)
Studio/1 bath, sleeps 4
$1,654 ($331/night)

Verified & Protected

Marriott's Timber Lodge Tahoe

South Lake Tahoe, California

Dec 14–19, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$1,987 ($397/night)

Verified & Protected Voted Top Pick 2025

Marriott's Desert Springs Villas II

Palm Desert, California

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,385 ($198/night)

Verified & Protected Voted Top Pick 2025

Pueblo Bonito Sunset Beach Resort & Spa

Cabo San Lucas, Mexico

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,987 ($284/night)

Verified & Protected

Los Cabos Golf Resort

Cabo San Lucas, Mexico

Dec 14–21, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$999 ($143/night)

Verified & Protected

The Westin St. John - Virgin Grand Villas

Cruz Bay, St. John (USVI)

Dec 14–21, 2025 (7 nights)
Studio/1 bath, sleeps 4
$4,276 ($611/night)

Verified & Protected Voted Top Pick 2025

Marriott's Barony Beach Club

Hilton Head Island, South Carolina

Dec 14–19, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$888 ($178/night)

Verified & Protected

Hyatt Windward Pointe Resort

Key West, Florida

Dec 14–18, 2025 (4 nights)
2 bed/2 bath, sleeps 6
$1,725 ($431/night)

Verified & Protected

The Ritz-Carlton Club, Vail

Vail, Colorado

Dec 14–18, 2025 (4 nights)
2 bed/2 bath, sleeps 6
$3,949 ($987/night)

Verified & Protected Voted Top Pick 2025

Marriott's Frenchman's Cove

Southside, St. Thomas (USVI)

Dec 14–21, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)