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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Marriott's Oceana Palms
Riviera Beach, Florida- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $3,568 ($714/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,744 ($1,249/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,148 ($735/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–16, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $6,510 ($1,085/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,242 ($248/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,379 ($476/night)
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Marriott's Summit Watch
Park City, Utah- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,339 ($223/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 10–16, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,172 ($195/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,374 ($196/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,619 ($374/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,292 ($899/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,638 ($806/night)
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The Villas at Disney's Grand Californian Hotel & Spa
Anaheim, California- Jan 10–14, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,397 ($599/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 10–16, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,145 ($191/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,183 ($312/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 10–16, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $693 ($115/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,167 ($595/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $2,505 ($417/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,671 ($810/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–15, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $7,107 ($1,421/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,213 ($243/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,295 ($471/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 10–24, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,765 ($126/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,462 ($292/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,242 ($248/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,003 ($201/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 10–13, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $959 ($320/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,488 ($298/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 10–14, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,379 ($595/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,600 ($1,086/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,642 ($274/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 10–15, 2027 (5 nights)
- 3 bed/3.5 bath, sleeps 8
- $10,925 ($2,185/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $9,726 ($1,389/night)
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Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $3,840 ($549/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,642 ($274/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,140 ($591/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
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Marriott's Harbour Club at Harbour Town
Hilton Head Island, South Carolina- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $887 ($177/night)