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- Feb 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($248/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/night)
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Westin Princeville Ocean Resort Villas
Princeville, Hawaii- Feb 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($441/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/3 bath, sleeps 8
- $7,655 ($1,094/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,031 ($576/night)
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,519 ($788/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,222 ($460/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $8,200 ($1,171/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $4,799 ($960/night)
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Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Feb 14–19, 2027 (5 nights)
- 1 bed/1 bath, sleeps 6
- $1,330 ($266/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $4,412 ($630/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,290 ($1,327/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,069 ($438/night)
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Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Feb 14–19, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $3,129 ($626/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $8,636 ($1,234/night)
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Grand Lodge on Peak 7
Breckenridge, Colorado- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,510 ($930/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,564 ($938/night)
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Sheraton Vistana Resort
Orlando, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,660 ($237/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,802 ($543/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,744 ($1,249/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 14–20, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,495 ($249/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,385 ($626/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 14–28, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,932 ($281/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 14–28, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,920 ($209/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,680 ($526/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 14–28, 2027 (14 nights)
- 3 bed/2 bath, sleeps 10
- $5,397 ($385/night)
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Marriott's Timber Lodge Tahoe
South Lake Tahoe, California- Feb 14–18, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($606/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,521 ($360/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Feb 14–21, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,977 ($1,140/night)
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The Ridge at Playa Grande
Cabo San Lucas, Mexico- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,878 ($268/night)
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Marriott's Summit Watch
Park City, Utah- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,336 ($905/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 14–18, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $3,426 ($856/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,418 ($1,203/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Feb 14–20, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,660 ($277/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,800 ($1,257/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Feb 14–19, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $2,689 ($538/night)
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Olympic Village Inn
Olympic Valley, California- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,123 ($303/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 14–21, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,306 ($329/night)
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Voted Top Pick 2026
Lagoon Tower by Hilton Grand Vacations
Honolulu, Hawaii- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,993 ($570/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,816 ($1,545/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Feb 14–16, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $1,244 ($622/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $7,441 ($1,063/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 14–21, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 14–19, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,198 ($240/night)