https://www.redweek.com/featured/winter-rentals en Mon, 27 Jul 2026 04:39:46 -0700 3600 Verified & Protected

Club Wyndham Smoky Mountains

Sevierville, Tennessee

• Dec 1–8, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $684 ($98/night)

]]> https://www.redweek.com/posting/R1502753 Sat, 25 Jul 2026 04:40:18 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

• Dec 1–6, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $1,312 ($262/night)

]]> https://www.redweek.com/posting/R1503327 Sun, 26 Jul 2026 13:17:46 -0700 Verified & Protected

The Westin Los Cabos Resort Villas & Spa

San Jose del Cabo, Mexico

• Dec 1–6, 2026 (5 nights)
• Studio/1 bath, sleeps 4
• $1,927 ($385/night)

]]> https://www.redweek.com/posting/R1495113 Wed, 08 Jul 2026 14:17:20 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 1–5, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $937 ($234/night)

]]> https://www.redweek.com/posting/R1453025 Fri, 27 Mar 2026 11:54:13 -0700 Verified & Protected Voted Top Pick 2026

Marriott's MountainSide at Park City

Park City, Utah

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1465014 Fri, 08 May 2026 10:53:44 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

• Dec 1–6, 2026 (5 nights)
• 2 bed/2 bath, sleeps 8
• $1,141 ($228/night)

]]> https://www.redweek.com/posting/R1503326 Sun, 26 Jul 2026 13:17:46 -0700 Verified & Protected

The Ritz-Carlton Club, Vail

Vail, Colorado

• Dec 1–6, 2026 (5 nights)
• 4 bed/4 bath, sleeps 10
• $8,690 ($1,738/night)

]]> https://www.redweek.com/posting/R1397772 Thu, 11 Dec 2025 08:09:52 -0800 Verified & Protected

The Ritz-Carlton Club, Vail

Vail, Colorado

• Dec 1–5, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $4,385 ($1,096/night)

]]> https://www.redweek.com/posting/R1410337 Mon, 05 Jan 2026 06:28:03 -0800 Verified & Protected

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

Vail, Colorado

• Dec 1–6, 2026 (5 nights)
• 2 bed/3 bath, sleeps 10
• $5,470 ($1,094/night)

]]> https://www.redweek.com/posting/R1502440 Fri, 24 Jul 2026 11:43:50 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 1–5, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $706 ($176/night)

]]> https://www.redweek.com/posting/R1453024 Fri, 27 Mar 2026 11:54:13 -0700 Verified & Protected

Club Wyndham Smoky Mountains

Sevierville, Tennessee

• Dec 1–8, 2026 (7 nights)
• 3 bed/2 bath, sleeps 10
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1502754 Sat, 25 Jul 2026 04:40:18 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• Dec 1–4, 2026 (3 nights)
• 1 bed/1 bath, sleeps 4
• $271 ($90/night)

]]> https://www.redweek.com/posting/R1476537 Tue, 26 May 2026 04:11:18 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

• Dec 1–6, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $568 ($114/night)

]]> https://www.redweek.com/posting/R1503324 Sun, 26 Jul 2026 13:17:46 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

• Dec 1–6, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $746 ($149/night)

]]> https://www.redweek.com/posting/R1503325 Sun, 26 Jul 2026 13:17:46 -0700 Verified & Protected

Marriott's Grand Residence Club, Mayfair-London

London, England

• Dec 1–8, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $6,510 ($930/night)

]]> https://www.redweek.com/posting/R1497481 Thu, 16 Jul 2026 13:55:33 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

• Dec 1–9, 2026 (8 nights)
• 2 bed/2 bath, sleeps 8
• $3,840 ($480/night)

]]> https://www.redweek.com/posting/R1418417 Fri, 16 Jan 2026 09:27:58 -0800 Verified & Protected Voted Top Pick 2026

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

Lahaina, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/3 bath, sleeps 8
• $5,911 ($844/night)

]]> https://www.redweek.com/posting/R1396693 Thu, 04 Dec 2025 19:07:57 -0800 Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

• Dec 1–7, 2026 (6 nights)
• Studio/1 bath, sleeps 4
• $2,804 ($467/night)

]]> https://www.redweek.com/posting/R1437659 Wed, 25 Feb 2026 10:15:08 -0800 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• Dec 1–4, 2026 (3 nights)
• 2 bed/2 bath, sleeps 8
• $367 ($122/night)

]]> https://www.redweek.com/posting/R1499352 Fri, 17 Jul 2026 11:13:00 -0700 Verified & Protected

Novaispania Residences by Pueblo Bonito

Cabo San Lucas, Mexico

• Dec 1–8, 2026 (7 nights)
• 4 bed/4.5 bath, sleeps 12
• $10,867 ($1,552/night)

]]> https://www.redweek.com/posting/R1420655 Mon, 16 Feb 2026 13:15:51 -0800 Verified & Protected

WorldMark Marina Dunes

Marina, California

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $2,505 ($358/night)

]]> https://www.redweek.com/posting/R1498944 Mon, 20 Jul 2026 08:44:40 -0700 Verified & Protected

The Ritz-Carlton Club, St. Thomas

East End, St. Thomas (USVI)

• Dec 1–6, 2026 (5 nights)
• 2 bed/2.5 bath, sleeps 6
• $4,112 ($822/night)

]]> https://www.redweek.com/posting/R1416086 Thu, 15 Jan 2026 11:56:36 -0800 Verified & Protected

The Ritz-Carlton Club, Vail

Vail, Colorado

• Dec 1–8, 2026 (7 nights)
• 3 bed/3.5 bath, sleeps 8
• $10,707 ($1,530/night)

]]> https://www.redweek.com/posting/R1496304 Tue, 14 Jul 2026 06:51:05 -0700 Verified & Protected

West 57th Street by Hilton Club

New York City, New York

• Dec 1–5, 2026 (4 nights)
• Studio/1 bath, sleeps 2
• $1,440 ($360/night)

]]> https://www.redweek.com/posting/R1462026 Fri, 24 Apr 2026 07:49:16 -0700 Verified & Protected

Sheraton Steamboat Resort Villas

Steamboat Springs, Colorado

• Dec 1–6, 2026 (5 nights)
• Studio/1 bath, sleeps 2
• $3,290 ($658/night)

]]> https://www.redweek.com/posting/R1495182 Tue, 14 Jul 2026 10:20:40 -0700

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

Vail, Colorado

• Dec 1–6, 2026 (5 nights)
• 1 bed/2 bath, sleeps 6
• $5,470 ($1,094/night)

]]> https://www.redweek.com/posting/R1503015 Sat, 25 Jul 2026 16:01:52 -0700 Verified & Protected Voted Top Pick 2026

Pueblo Bonito Sunset Beach Resort & Spa

Cabo San Lucas, Mexico

• Dec 1–8, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $1,550 ($221/night)

]]> https://www.redweek.com/posting/R1438547 Fri, 20 Mar 2026 14:11:29 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $3,458 ($494/night)

]]> https://www.redweek.com/posting/R1469896 Thu, 07 May 2026 13:28:48 -0700 Verified & Protected Voted #1 Resort 2026

Marriott's Aruba Surf Club

Palm Beach, Aruba

• Dec 1–8, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $2,967 ($424/night)

]]> https://www.redweek.com/posting/R1396837 Fri, 05 Dec 2025 17:16:02 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,874 ($839/night)

]]> https://www.redweek.com/posting/R1451153 Thu, 26 Mar 2026 13:58:53 -0700 Verified & Protected

Club Wyndham Avenue Plaza

New Orleans, Louisiana

• Dec 1–4, 2026 (3 nights)
• 1 bed/1 bath, sleeps 4
• $415 ($138/night)

]]> https://www.redweek.com/posting/R1494286 Mon, 06 Jul 2026 21:49:12 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–8, 2026 (7 nights)
• 3 bed/3 bath, sleeps 10
• $10,489 ($1,498/night)

]]> https://www.redweek.com/posting/R1411325 Wed, 07 Jan 2026 07:53:14 -0800 Verified & Protected

Sheraton Steamboat Resort Villas

Steamboat Springs, Colorado

• Dec 1–6, 2026 (5 nights)
• Studio/1 bath, sleeps 4
• $4,380 ($876/night)

]]> https://www.redweek.com/posting/R1495306 Thu, 09 Jul 2026 08:21:18 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

• Dec 1–7, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $1,299 ($217/night)

]]> https://www.redweek.com/posting/R1495975 Fri, 10 Jul 2026 05:46:46 -0700 Verified & Protected

Club Wyndham Avenue Plaza

New Orleans, Louisiana

• Dec 1–4, 2026 (3 nights)
• Studio/1 bath, sleeps 2
• $367 ($122/night)

]]> https://www.redweek.com/posting/R1494285 Mon, 06 Jul 2026 21:49:12 -0700 Verified & Protected

Pueblo Bonito Rose Spa & Resort

Cabo San Lucas, Mexico

• Dec 1–8, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $1,109 ($158/night)

]]> https://www.redweek.com/posting/R1474697 Wed, 20 May 2026 12:15:25 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–8, 2026 (7 nights)
• Studio/1 bath, sleeps 2
• $2,641 ($377/night)

]]> https://www.redweek.com/posting/R1446056 Tue, 24 Mar 2026 09:06:52 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kaanapali Ocean Resort Villas

Lahaina, Hawaii

• Dec 1–6, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $2,423 ($485/night)

]]> https://www.redweek.com/posting/R1471899 Tue, 19 May 2026 09:00:22 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

• Dec 1–6, 2026 (5 nights)
• 3 bed/3 bath, sleeps 10
• $2,750 ($550/night)

]]> https://www.redweek.com/posting/R1431841 Mon, 16 Feb 2026 07:14:51 -0800 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

• Dec 1–7, 2026 (6 nights)
• 1 bed/1 bath, sleeps 4
• $852 ($142/night)

]]> https://www.redweek.com/posting/R1496794 Sat, 11 Jul 2026 15:37:00 -0700 Verified & Protected

Club Wyndham Bali Hai Villas

Princeville, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,295 ($471/night)

]]> https://www.redweek.com/posting/R1493960 Mon, 06 Jul 2026 09:50:31 -0700 Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 1–5, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $499 ($125/night)

]]> https://www.redweek.com/posting/R1499041 Thu, 16 Jul 2026 14:49:00 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

• Dec 1–7, 2026 (6 nights)
• 2 bed/2 bath, sleeps 8
• $1,488 ($248/night)

]]> https://www.redweek.com/posting/R1495976 Fri, 10 Jul 2026 05:46:46 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

• Dec 1–7, 2026 (6 nights)
• 1 bed/1 bath, sleeps 4
• $639 ($107/night)

]]> https://www.redweek.com/posting/R1496793 Sat, 11 Jul 2026 15:37:00 -0700 Verified & Protected

Disney's Riviera Resort

Lake Buena Vista, Florida

• Dec 1–2, 2026 (1 night)
• Studio/1 bath, sleeps 5
• $622 ($622/night)

]]> https://www.redweek.com/posting/R1411267 Fri, 02 Jan 2026 19:10:26 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–7, 2026 (6 nights)
• 3 bed/3 bath, sleeps 10
• $7,862 ($1,310/night)

]]> https://www.redweek.com/posting/R1412939 Tue, 06 Jan 2026 08:35:14 -0800 Verified & Protected

Disney's Animal Kingdom Villas - Jambo House

Lake Buena Vista, Florida

• Dec 1–5, 2026 (4 nights)
• 1 bed/1 bath, sleeps 5
• $7,010 ($1,752/night)

]]> https://www.redweek.com/posting/R1413441 Tue, 06 Jan 2026 18:08:35 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $5,671 ($810/night)

]]> https://www.redweek.com/posting/R1434890 Thu, 19 Feb 2026 12:27:28 -0800