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 Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,474 ($782/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–19, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($608/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 10–24, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,321 ($237/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 10–24, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,589 ($185/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–24, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,222 ($159/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 Aruba Ocean Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,365 ($766/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–24, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $4,280 ($306/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,365 ($766/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–24, 2027 (14 nights)
- 3 bed/2 bath, sleeps 10
- $4,054 ($290/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–24, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $4,054 ($290/night)
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,458 ($494/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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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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Hyatt Sunset Harbor Resort
Key West, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $5,693 ($813/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,783 ($969/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($331/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/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
- $6,565 ($938/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
- $6,020 ($860/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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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,314 ($463/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,532 ($362/night)
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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 Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,859 ($408/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 Aruba Ocean Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,930 ($704/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 10–16, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $487 ($81/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 #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 Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–17, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,598 ($1,514/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,786 ($541/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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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
- $6,565 ($938/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
- $3,840 ($549/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–14, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($497/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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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–14, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,987 ($497/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,238 ($891/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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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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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,911 ($844/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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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)