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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Sands of Kahana Vacation Club
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,132 ($447/night)
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Grand Timber Lodge
Breckenridge, Colorado- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,042 ($292/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–12, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $604 ($201/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 9–12, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $427 ($142/night)
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The Westin Los Cabos Resort Villas & Spa
San Jose del Cabo, Mexico- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,398 ($343/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Jan 9 – Feb 6, 2027 (28 nights)
- 3 bed/2.5 bath, sleeps 8
- $26,883 ($960/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $10,488 ($1,498/night)
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Club Wyndham Inn on Long Wharf
Newport, Rhode Island- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $503 ($72/night)
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Voted Top Pick 2026
Marriott's Frenchman's Cove
Southside, St. Thomas (USVI)- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,365 ($766/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 9–23, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,489 ($249/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Jan 9–16, 2027 (7 nights)
- 2 bed/2.5 bath, sleeps 6
- $8,745 ($1,249/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,794 ($685/night)
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Marriott's Canyon Villas at Desert Ridge
Phoenix, Arizona- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,595 ($656/night)
Voted Top Pick 2026
Hyatt Vacation Club at Ka’anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,783 ($969/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,252 ($750/night)
Hilton Vacation Club Kaanapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/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 Ocean Pointe
Palm Beach Shores, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($449/night)
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Club Wyndham Inn on Long Wharf
Newport, Rhode Island- Jan 10–13, 2027 (3 nights)
- 1 bed/1 bath, sleeps 4
- $199 ($66/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $6,565 ($1,313/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Jan 10–15, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $3,082 ($616/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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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
- $6,129 ($876/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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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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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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Westgate Park City Resort & Spa
Park City, Utah- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,330 ($619/night)
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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/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
- $3,840 ($549/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/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
- $5,366 ($767/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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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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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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Voted Top Pick 2026
Marriott's Grande Ocean
Hilton Head Island, South Carolina- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,385 ($277/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 Ko Olina Beach Club
Kapolei, Hawaii- Jan 10–16, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $4,596 ($766/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 10–14, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,074 ($519/night)
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Club Wyndham Inn on Long Wharf
Newport, Rhode Island- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $503 ($72/night)
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Club Wyndham Long Wharf
Newport, Rhode Island- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $839 ($120/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
- $6,020 ($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
- $5,671 ($810/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
- $6,320 ($903/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $3,573 ($595/night)
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Copper Creek Villas & Cabins at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Jan 10–16, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,298 ($550/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 Long Wharf
Newport, Rhode Island- Jan 10–13, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $307 ($102/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)