Winter Rentals | RedWeek

Verified & Protected

Westin Desert Willow

Palm Desert, California

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$2,276 ($325/night)

Verified & Protected

Island Club - Ocean View

Hilton Head Island, South Carolina

Dec 20–27, 2025 (7 nights)
1 bed/2 bath, sleeps 6
$1,330 ($190/night)

Verified & Protected Voted Top Pick 2025

Divi Aruba Phoenix Beach Resort

Palm Beach, Aruba

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$2,750 ($393/night)

Verified & Protected

Marriott's Grand Chateau

Las Vegas, Nevada

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,932 ($276/night)

Verified & Protected

Marriott's St. Kitts Beach Club

Frigate Bay, St. Kitts

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,627 ($375/night)

Verified & Protected

Hilton Vacation Club Kaanapali Beach

Lahaina, Hawaii

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$3,568 ($510/night)

Verified & Protected

Marriott's Shadow Ridge - The Villages

Palm Desert, California

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,385 ($198/night)

Verified & Protected

Westgate Smoky Mountain Resort & Water Park

Gatlinburg, Tennessee

Dec 20–27, 2025 (7 nights)
4 bed/4 bath, sleeps 16
$3,649 ($521/night)

Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

Dec 20–27, 2025 (7 nights)
1 bed/2 bath, sleeps 4
$1,987 ($284/night)

Verified & Protected

Paradise Point Resort

Hollister, Missouri

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,110 ($159/night)

Verified & Protected

Club Regina Los Cabos

San Jose del Cabo, Mexico

Dec 20–27, 2025 (7 nights)
2 bed/3 bath, sleeps 6
$4,385 ($626/night)

Verified & Protected

Hilton Grand Vacations Club Zihuatanejo

Ixtapa Zihuatanejo, Mexico

Dec 20–27, 2025 (7 nights)
3 bed/3 bath, sleeps 8
$2,641 ($377/night)

Verified & Protected

Marriott's Shadow Ridge - The Villages

Palm Desert, California

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

Verified & Protected

Club Wyndham Oceanside Pier Resort

Oceanside, California

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,549 ($221/night)

Verified & Protected

Club Regina Puerto Vallarta

Puerto Vallarta, Mexico

Dec 20–27, 2025 (7 nights)
2 bed/3 bath, sleeps 6
$1,330 ($190/night)

Verified & Protected

Paniolo Greens

Waikoloa Village, Hawaii

Dec 20–26, 2025 (6 nights)
2 bed/1 bath, sleeps 6
$1,054 ($176/night)

Verified & Protected Voted Top Pick 2025

Marriott's OceanWatch Villas at Grande Dunes

Myrtle Beach, South Carolina

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,294 ($471/night)

Verified & Protected

The Resort on Cocoa Beach

Cocoa Beach, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,275 ($182/night)

Verified & Protected Voted Top Pick 2025

Harborside Resort at Atlantis

Paradise Island, Bahamas

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$2,968 ($424/night)

Verified & Protected Voted Top Pick 2025

Hyatt Vacation Club at Ka’anapali Beach

Lahaina, Hawaii

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$3,186 ($455/night)

Verified & Protected

Villa del Palmar at the Islands of Loreto

Loreto, Mexico

Dec 20–27, 2025 (7 nights)
2 bed/3 bath, sleeps 6
$4,603 ($658/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–28, 2025 (8 nights)
1 bed/1 bath, sleeps 4
$1,385 ($173/night)

Verified & Protected

Camaron Cove Resort

Indian Rocks Beach, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,205 ($315/night)

Verified & Protected

Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,878 ($268/night)

Verified & Protected

Orlando International Resort Club

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$555 ($79/night)

Verified & Protected Voted Top Pick 2025

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

Dec 20–27, 2025 (7 nights)
Studio/1 bath, sleeps 4
$3,649 ($521/night)

Verified & Protected

Westin Desert Willow

Palm Desert, California

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,110 ($159/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$4,494 ($642/night)

Verified & Protected

Grand Residences by Royal Resorts

Puerto Morelos, Mexico

Dec 20–27, 2025 (7 nights)
2 bed/2.5 bath, sleeps 8
$3,995 ($571/night)

Verified & Protected

Royal Haciendas

Playa del Carmen, Mexico

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,039 ($291/night)

Verified & Protected

The Westin Lagunamar Ocean Resort Villas & Spa

Cancun, Mexico

Dec 20–27, 2025 (7 nights)
Studio/1 bath, sleeps 4
$1,157 ($165/night)

Verified & Protected

Villa del Arco Beach Resort & Spa

Cabo San Lucas, Mexico

Dec 20–27, 2025 (7 nights)
2 bed/3 bath, sleeps 6
$2,096 ($299/night)

Verified & Protected

Villa del Arco Beach Resort & Spa

Cabo San Lucas, Mexico

Dec 20–27, 2025 (7 nights)
1 bed/2 bath, sleeps 4
$2,967 ($424/night)

Verified & Protected

The Westin Mission Hills Villas

Rancho Mirage, California

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,390 ($341/night)

Verified & Protected

Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,358 ($194/night)

Verified & Protected Voted Top Pick 2025

Marriott's Desert Springs Villas II

Palm Desert, California

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,878 ($268/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,286 ($184/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,286 ($184/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

Verified & Protected Voted Top Pick 2025

The Royal Sands

Cancun, Mexico

Dec 20–27, 2025 (7 nights)
Studio/1 bath, sleeps 2
$1,110 ($159/night)

Verified & Protected Voted Top Pick 2025

Marriott's Maui Ocean Club - Lahaina Tower

Lahaina, Hawaii

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$8,631 ($1,233/night)

Verified & Protected

Marriott's Kauai Lagoons - Kalanipu'u

Lihue, Hawaii

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$3,290 ($470/night)

Verified & Protected Voted Top Pick 2025

Marriott's MountainSide at Park City

Park City, Utah

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,186 ($455/night)

Verified & Protected Voted Top Pick 2025

Harborside Resort at Atlantis

Paradise Island, Bahamas

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$2,641 ($377/night)

Verified & Protected

The Point at Poipu

Koloa, Hawaii

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$3,622 ($517/night)

Verified & Protected

Divi Village Golf and Beach Resort

Oranjestad, Aruba

Dec 20–27, 2025 (7 nights)
1 bed/2 bath, sleeps 4
$2,423 ($346/night)

Verified & Protected

Marriott's Kauai Beach Club

Lihue, Hawaii

Dec 20–27, 2025 (7 nights)
Studio/1 bath, sleeps 2
$3,508 ($501/night)

Verified & Protected

Marriott's Oceana Palms

Riviera Beach, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$4,222 ($603/night)