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 Bali Hai Villas
Princeville, Hawaii- Jan 12–21, 2027 (9 nights)
- 2 bed/2 bath, sleeps 6
- $3,539 ($393/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 12–21, 2027 (9 nights)
- 3 bed/2 bath, sleeps 10
- $2,528 ($281/night)
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Club Wyndham Bali Hai Villas
Princeville, Hawaii- Jan 12–21, 2027 (9 nights)
- 2 bed/2 bath, sleeps 6
- $4,080 ($453/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 12–17, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $2,096 ($419/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 12–16, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $439 ($110/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Club Wyndham Harbour Lights
San Diego, California- Jan 12–16, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $764 ($191/night)
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The Ritz-Carlton Club, Vail
Vail, Colorado- Jan 12–16, 2027 (4 nights)
- 3 bed/3.5 bath, sleeps 8
- $8,309 ($2,077/night)
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Club Wyndham Harbour Lights
San Diego, California- Jan 12–15, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $487 ($162/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 12–19, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Pueblo Bonito Rose Spa & Resort
Cabo San Lucas, Mexico- Jan 13–20, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,200 ($314/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–27, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $3,321 ($237/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–18, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,276 ($255/night)
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Club Wyndham Nashville
Nashville, Tennessee- Jan 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $503 ($72/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–20, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,584 ($798/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 13–17, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $1,909 ($477/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–20, 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 13–18, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($310/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 13–17, 2027 (4 nights)
- 3 bed/3 bath, sleeps 10
- $3,513 ($878/night)
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Club Wyndham Nashville
Nashville, Tennessee- Jan 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,057 ($151/night)
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Club Wyndham Nashville
Nashville, Tennessee- Jan 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $684 ($98/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–18, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,566 ($313/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 13–17, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $1,909 ($477/night)
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Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Jan 13–16, 2027 (3 nights)
- 2 bed/2 bath, sleeps 6
- $1,873 ($624/night)
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WorldMark Kona Resort
Kailua-Kona, Hawaii- Jan 13–20, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,658 ($237/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–27, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,222 ($159/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 13–17, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $1,909 ($477/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–27, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $4,280 ($306/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–18, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($310/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 13–20, 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 13–27, 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 13–18, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $852 ($170/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–18, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $1,077 ($269/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–18, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $1,271 ($318/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Jan 14–19, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $1,932 ($386/night)
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Villa del Palmar Cancun Luxury Beach Resort & Spa
Cancun, Mexico- Jan 14–21, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $3,186 ($455/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,726 ($532/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $839 ($120/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $852 ($170/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,566 ($313/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–19, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($310/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,550 ($310/night)
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,976 ($997/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)