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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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 16–30, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,016 ($215/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 16–30, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,920 ($209/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 16–17, 2027 (1 night)
- Studio/1 bath, sleeps 5
- $586 ($586/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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The Westin St. John - Bay Vista Villas
Cruz Bay, St. John (USVI)- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,200 ($1,171/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,019 ($860/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,831 ($404/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,859 ($408/night)
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Marriott's Summit Watch
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 16–22, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $4,145 ($691/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,474 ($782/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,740 ($820/night)
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Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,948 ($564/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,358 ($765/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,513 ($502/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 16–20, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,220 ($305/night)
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Pueblo Bonito Rose Spa & Resort
Cabo San Lucas, Mexico- Jan 16–23, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,200 ($314/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,166 ($595/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,464 ($1,066/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,968 ($424/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 16–23, 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 16–22, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $4,598 ($766/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $7,650 ($1,093/night)
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Divi Dutch Village Beach Resort
Oranjestad, Aruba- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $7,655 ($1,094/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–19, 2027 (3 nights)
- 3 bed/2 bath, sleeps 10
- $901 ($300/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,290 ($470/night)
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,758 ($965/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,977 ($711/night)
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Novaispania Residences by Pueblo Bonito
Cabo San Lucas, Mexico- Jan 16–23, 2027 (7 nights)
- 4 bed/4.5 bath, sleeps 12
- $9,071 ($1,296/night)
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The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,276 ($611/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,532 ($362/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 16–21, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,406 ($481/night)
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Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 16–23, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,898 ($1,557/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–29, 2027 (13 nights)
- 1 bed/1 bath, sleeps 4
- $2,000 ($154/night)
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The Cliff Club at Snowbird
Snowbird, Utah- Jan 16–23, 2027 (7 nights)
- 2 bed/3 bath, sleeps 10
- $13,105 ($1,872/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,045 ($1,006/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,268 ($467/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
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Club Wyndham Orange Tree Golf Resort
Scottsdale, Arizona- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 16–23, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 16–23, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)