https://www.redweek.com/featured/winter-rentals?sort=date en Sun, 05 Apr 2026 12:56:41 -0700 3600 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• Dec 1–6, 2026 (5 nights)
• 1 bed/1 bath, sleeps 4
• $586 ($117/night)

]]> https://www.redweek.com/posting/R1434568 Mon, 16 Feb 2026 22:47:38 -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 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 CHOOSE YOUR OWN DATES

Club Wyndham Orange Tree Golf Resort

Scottsdale, Arizona

• Dec 1–12, 2026 (11 nights)
• 1 bed/1 bath, sleeps 4
• $1,725 ($157/night)

]]> https://www.redweek.com/posting/R1444246 Tue, 10 Mar 2026 10:20:31 -0700 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

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 CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• Dec 1–12, 2026 (11 nights)
• 3 bed/2 bath, sleeps 10
• $2,406 ($219/night)

]]> https://www.redweek.com/posting/R1454302 Mon, 30 Mar 2026 13:52:16 -0700 Verified & Protected

The Ritz-Carlton Club, Vail

Vail, Colorado

• Dec 1–6, 2026 (5 nights)
• 4 bed/4 bath, sleeps 10
• $10,925 ($2,185/night)

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

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

• Dec 1–5, 2026 (4 nights)
• 1 bed/1 bath, sleeps 4
• $427 ($107/night)

]]> https://www.redweek.com/posting/R1431275 Tue, 10 Feb 2026 10:37:11 -0800 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham South Shore

Zephyr Cove, Nevada

• Dec 1–5, 2026 (4 nights)
• 3 bed/2 bath, sleeps 8
• $940 ($235/night)

]]> https://www.redweek.com/posting/R1449890 Sun, 22 Mar 2026 11:32:04 -0700 Verified & Protected

Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

• Dec 1–6, 2026 (5 nights)
• Studio/1 bath, sleeps 4
• $2,680 ($536/night)

]]> https://www.redweek.com/posting/R1410542 Thu, 01 Jan 2026 18:08:39 -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 Resort at Diamante

Cabo San Lucas, Mexico

• Dec 1–10, 2026 (9 nights)
• 1 bed/2 bath, sleeps 4
• $4,712 ($524/night)

]]> https://www.redweek.com/posting/R1405674 Mon, 22 Dec 2025 14:21:49 -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

Hyatt Main Street Station, A Hyatt Residence Club

Breckenridge, Colorado

• Dec 1–5, 2026 (4 nights)
• Studio/1 bath, sleeps 4
• $622 ($155/night)

]]> https://www.redweek.com/posting/R1413645 Mon, 19 Jan 2026 14:43:35 -0800 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

Marriott's Summit Watch

Park City, Utah

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $6,020 ($860/night)

]]> https://www.redweek.com/posting/R1415652 Sun, 18 Jan 2026 23:28:58 -0800 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

The Westin St. John - Sunset Bay Villas

Cruz Bay, St. John (USVI)

• Dec 1–8, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $7,110 ($1,016/night)

]]> https://www.redweek.com/posting/R1442509 Fri, 06 Mar 2026 11:32:08 -0800 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

Aulani, a Disney Resort & Spa

Kapolei, Hawaii

• Dec 1–7, 2026 (6 nights)
• Studio/1 bath, sleeps 4
• $2,968 ($495/night)

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

Club Wyndham Cypress Palms

Kissimmee, Florida

• Dec 1–5, 2026 (4 nights)
• 2 bed/2 bath, sleeps 8
• $830 ($208/night)

]]> https://www.redweek.com/posting/R1453026 Fri, 27 Mar 2026 11:54:13 -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
• $2,505 ($358/night)

]]> https://www.redweek.com/posting/R1447102 Thu, 26 Mar 2026 12:06:36 -0700 Verified & Protected

Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

• Dec 1–6, 2026 (5 nights)
• Studio/1 bath, sleeps 4
• $2,726 ($545/night)

]]> https://www.redweek.com/posting/R1410543 Thu, 01 Jan 2026 18:08:39 -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

Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

• Dec 1–6, 2026 (5 nights)
• Studio/1 bath, sleeps 4
• $2,749 ($550/night)

]]> https://www.redweek.com/posting/R1410544 Thu, 01 Jan 2026 18:08:39 -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 - Kidani Village

Lake Buena Vista, Florida

• Dec 1–6, 2026 (5 nights)
• Studio/1 bath, sleeps 4
• $2,772 ($554/night)

]]> https://www.redweek.com/posting/R1411220 Fri, 02 Jan 2026 18:08:40 -0800 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham South Shore

Zephyr Cove, Nevada

• Dec 1–5, 2026 (4 nights)
• 2 bed/2 bath, sleeps 6
• $697 ($174/night)

]]> https://www.redweek.com/posting/R1449889 Sun, 22 Mar 2026 11:32:04 -0700 Verified & Protected

Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

• Dec 1–7, 2026 (6 nights)
• Studio/1 bath, sleeps 4
• $3,213 ($536/night)

]]> https://www.redweek.com/posting/R1411221 Fri, 02 Jan 2026 18:08:40 -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

Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

• Dec 1–5, 2026 (4 nights)
• Studio/1 bath, sleeps 4
• $2,147 ($537/night)

]]> https://www.redweek.com/posting/R1411222 Fri, 02 Jan 2026 18:08:40 -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
• $6,129 ($876/night)

]]> https://www.redweek.com/posting/R1403989 Tue, 16 Dec 2025 07:10:44 -0800 Verified & Protected

Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

• Dec 1–3, 2026 (2 nights)
• Studio/1 bath, sleeps 4
• $1,066 ($533/night)

]]> https://www.redweek.com/posting/R1411225 Fri, 02 Jan 2026 18:08:41 -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

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 1–9, 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

Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

• Dec 1–5, 2026 (4 nights)
• Studio/1 bath, sleeps 4
• $1,495 ($374/night)

]]> https://www.redweek.com/posting/R1410552 Thu, 01 Jan 2026 18:10:36 -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

Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

• Dec 1–7, 2026 (6 nights)
• Studio/1 bath, sleeps 4
• $2,260 ($377/night)

]]> https://www.redweek.com/posting/R1410554 Thu, 01 Jan 2026 18:10:36 -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 Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

• Dec 1–8, 2026 (7 nights)
• Studio/1 bath, sleeps 4
• $2,614 ($373/night)

]]> https://www.redweek.com/posting/R1410555 Thu, 01 Jan 2026 18:10:36 -0800 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Grand Desert

Las Vegas, Nevada

• Dec 2–9, 2026 (7 nights)
• 2 bed/2 bath, sleeps 8
• $1,725 ($246/night)

]]> https://www.redweek.com/posting/R1450920 Tue, 24 Mar 2026 16:12:46 -0700 Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Grand Desert

Las Vegas, Nevada

• Dec 2–9, 2026 (7 nights)
• 3 bed/2 bath, sleeps 8
• $2,275 ($325/night)

]]> https://www.redweek.com/posting/R1450921 Tue, 24 Mar 2026 16:12:46 -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

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

Montecristo Estates by Pueblo Bonito

Cabo San Lucas, Mexico

• Dec 2–9, 2026 (7 nights)
• 3 bed/3.5 bath, sleeps 10
• $3,186 ($455/night)

]]> https://www.redweek.com/posting/R1445591 Thu, 12 Mar 2026 15:00:04 -0700