https://www.redweek.com/featured/winter-rentals en Mon, 06 Jul 2026 00:54:57 -0700 3600 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 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

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

Disney's Beach Club Villas

Lake Buena Vista, Florida

• Dec 1–3, 2026 (2 nights)
• Studio/1 bath, sleeps 5
• $1,277 ($639/night)

]]> https://www.redweek.com/posting/R1468256 Sat, 02 May 2026 19:08:57 -0700 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 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

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

Novaispania Residences by Pueblo Bonito

Cabo San Lucas, Mexico

• Dec 1–8, 2026 (7 nights)
• 4 bed/4.5 bath, sleeps 12
• $10,870 ($1,553/night)

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

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–6, 2026 (5 nights)
• Studio/1 bath, sleeps 2
• $2,684 ($537/night)

]]> https://www.redweek.com/posting/R1491148 Wed, 01 Jul 2026 10:58:52 -0700 Verified & Protected Voted Top Pick 2026

The Royal Sands

Cancun, Mexico

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $1,660 ($237/night)

]]> https://www.redweek.com/posting/R1490513 Wed, 01 Jul 2026 11:05:54 -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

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 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 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

Garza Blanca Resort & Spa Cancun

Cancun, Mexico

• Dec 1–10, 2026 (9 nights)
• 2 bed/2 bath, sleeps 6
• $10,707 ($1,190/night)

]]> https://www.redweek.com/posting/R1473040 Tue, 16 Jun 2026 09:49:40 -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 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

West 57th Street by Hilton Club

New York City, New York

• Dec 1–5, 2026 (4 nights)
• Studio/1 bath, sleeps 2
• $1,660 ($415/night)

]]> https://www.redweek.com/posting/R1462026 Fri, 24 Apr 2026 07:49:16 -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
• $5,874 ($839/night)

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

Marriott's Summit Watch

Park City, Utah

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,930 ($704/night)

]]> https://www.redweek.com/posting/R1415652 Sun, 18 Jan 2026 23:28:58 -0800 Verified & Protected Voted Top Pick 2026

Marriott's Ko Olina Beach Club

Kapolei, Hawaii

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,669 ($953/night)

]]> https://www.redweek.com/posting/R1454724 Tue, 31 Mar 2026 10:57:11 -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 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

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 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 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

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

Montecristo Estates by Pueblo Bonito

Cabo San Lucas, Mexico

• Dec 1–8, 2026 (7 nights)
• 3 bed/3.5 bath, sleeps 10
• $3,069 ($438/night)

]]> https://www.redweek.com/posting/R1480674 Mon, 08 Jun 2026 11:59:08 -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

Marriott Vacation Club, Waikiki

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $2,260 ($323/night)

]]> https://www.redweek.com/posting/R1407461 Fri, 26 Dec 2025 12:44:20 -0800 Verified & Protected

The Ritz-Carlton Club, Vail

Vail, Colorado

• Dec 2–6, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $4,821 ($1,205/night)

]]> https://www.redweek.com/posting/R1440168 Tue, 03 Mar 2026 13:59:29 -0800 Verified & Protected Voted #1 Resort 2026

Marriott's Aruba Surf Club

Palm Beach, Aruba

• Dec 2–9, 2026 (7 nights)
• 1 bed/1 bath, sleeps 4
• $3,802 ($543/night)

]]> https://www.redweek.com/posting/R1457285 Wed, 01 Jul 2026 07:55:27 -0700 Verified & Protected

Club Wyndham Royal Sea Cliff

Kailua-Kona, Hawaii

• Dec 2–7, 2026 (5 nights)
• 2 bed/2 bath, sleeps 6
• $1,987 ($397/night)

]]> https://www.redweek.com/posting/R1448659 Wed, 06 May 2026 15:07:58 -0700 Verified & Protected

Montecristo Estates by Pueblo Bonito

Cabo San Lucas, Mexico

• Dec 2–9, 2026 (7 nights)
• 3 bed/3.5 bath, sleeps 10
• $3,404 ($486/night)

]]> https://www.redweek.com/posting/R1465414 Wed, 29 Apr 2026 11:57:00 -0700 Verified & Protected

WorldMark Las Vegas - Boulevard

Las Vegas, Nevada

• Dec 2–8, 2026 (6 nights)
• 2 bed/2 bath, sleeps 6
• $1,659 ($276/night)

]]> https://www.redweek.com/posting/R1459021 Thu, 16 Apr 2026 14:56:21 -0700 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $4,707 ($672/night)

]]> https://www.redweek.com/posting/R1486313 Fri, 19 Jun 2026 09:53:44 -0700 Verified & Protected Voted Top Pick 2026

Marriott's MountainSide at Park City

Park City, Utah

• Dec 2–6, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $2,042 ($510/night)

]]> https://www.redweek.com/posting/R1467105 Mon, 18 May 2026 10:46:18 -0700 Verified & Protected

The Ritz-Carlton Club, Vail

Vail, Colorado

• Dec 2–7, 2026 (5 nights)
• 3 bed/3.5 bath, sleeps 8
• $9,835 ($1,967/night)

]]> https://www.redweek.com/posting/R1422652 Mon, 02 Feb 2026 06:31:35 -0800 Verified & Protected Voted Top Pick 2026

Lagoon Tower by Hilton Grand Vacations

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 6
• $3,568 ($510/night)

]]> https://www.redweek.com/posting/R1478058 Tue, 02 Jun 2026 06:55:13 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• Dec 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $995 ($142/night)

]]> https://www.redweek.com/posting/R1468305 Sun, 03 May 2026 04:41:04 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• Dec 2–6, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $648 ($162/night)

]]> https://www.redweek.com/posting/R1432951 Fri, 13 Feb 2026 17:26:27 -0800 Verified & Protected

Imperial Hawaii Vacation Club

Honolulu, Hawaii

• Dec 2–9, 2026 (7 nights)
• 1 bed/2 bath, sleeps 6
• $1,649 ($236/night)

]]> https://www.redweek.com/posting/R1439465 Thu, 07 May 2026 07:33:18 -0700 Verified & Protected Voted Top Pick 2026

Marriott's Waiohai Beach Club

Koloa, Hawaii

• Dec 3–12, 2026 (9 nights)
• 2 bed/2 bath, sleeps 8
• $8,200 ($911/night)

]]> https://www.redweek.com/posting/R1443767 Tue, 17 Mar 2026 08:00:24 -0700 Verified & Protected Voted Top Pick 2026

The Westin Kierland Villas

Scottsdale, Arizona

• Dec 3–8, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $2,204 ($441/night)

]]> https://www.redweek.com/posting/R1479014 Mon, 01 Jun 2026 13:08:00 -0700 Verified & Protected

The Westin Riverfront Mountain Villas

Avon, Colorado

• Dec 3–8, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $3,840 ($768/night)

]]> https://www.redweek.com/posting/R1481313 Mon, 08 Jun 2026 14:11:37 -0700 Verified & Protected

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

• Dec 3–7, 2026 (4 nights)
• Studio/1 bath, sleeps 4
• $2,188 ($547/night)

]]> https://www.redweek.com/posting/R1483217 Fri, 12 Jun 2026 17:08:39 -0700 Verified & Protected

The Ritz-Carlton Club, Vail

Vail, Colorado

• Dec 3–7, 2026 (4 nights)
• 3 bed/3.5 bath, sleeps 8
• $7,873 ($1,968/night)

]]> https://www.redweek.com/posting/R1422656 Mon, 02 Feb 2026 06:29:28 -0800 Verified & Protected

Marriott's Villas at Doral

Miami, Florida

• Dec 3–10, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $4,382 ($626/night)

]]> https://www.redweek.com/posting/R1442598 Fri, 13 Mar 2026 14:24:00 -0700