Winter Timeshare Rentals
Winter getaways are always popular, making now the perfect time to secure exclusive timeshare deals for your seasonal escape! Whether you're dreaming of a snowy mountain retreat or a warm-weather getaway, these timeshare rentals offer the perfect setting to make your winter vacation unforgettable.
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,458 ($494/night)
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Hanalei Bay Resort
Princeville, Hawaii- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $2,696 ($385/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 9, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,519 ($169/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,015 ($1,716/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $5,038 ($720/night)
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Marriott Vacation Club, New York City
New York City, New York- Dec 31, 2026 – Jan 3, 2027 (3 nights)
- Studio/1 bath, sleeps 2
- $4,385 ($1,462/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 31, 2026 – Jan 5, 2027 (5 nights)
- 1 bed/3 bath, sleeps 8
- $2,478 ($496/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 3, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,748 ($583/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 4, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,730 ($683/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,334 ($1,333/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,088 ($1,584/night)
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Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Dec 31, 2026 – Jan 5, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $4,821 ($964/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,726 ($532/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Club Wyndham Nashville
Nashville, Tennessee- Jan 1–5, 2027 (4 nights)
- 2 bed/2 bath, sleeps 6
- $479 ($120/night)
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Renaissance Wind Creek Aruba - Ocean Suites
Oranjestad, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,222 ($603/night)
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The Point at Poipu
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,260 ($252/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,835 ($548/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 1–3, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $866 ($433/night)
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Hyatt Vacation Club at Northstar Lodge
Truckee, California- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $11,852 ($1,693/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,564 ($938/night)
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WorldMark Midway
Midway, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,083 ($1,012/night)
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Sheraton Mountain Vista Villas
Avon, Colorado- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($517/night)
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Club Wyndham Nashville
Nashville, Tennessee- Jan 1–5, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $710 ($178/night)
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Hyatt Pinon Pointe
Sedona, Arizona- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
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Westgate Flamingo Bay
Las Vegas, Nevada- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,087 ($155/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $995 ($142/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 1–4, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,119 ($373/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,121 ($874/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 1–8, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,750 ($393/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,893 ($699/night)
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Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,306 ($329/night)
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Marriott's St. Kitts Beach Club
Frigate Bay, St. Kitts- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $4,057 ($580/night)
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,031 ($576/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,859 ($408/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,696 ($242/night)
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Marriott's Royal Palms
Orlando, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,306 ($329/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,380 ($1,483/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–5, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,458 ($614/night)