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 Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,094 ($728/night)
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Grand Waikikian by Hilton Grand Vacations
Honolulu, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,892 ($985/night)
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Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
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Club Wyndham SeaWatch Resort
Myrtle Beach, South Carolina- Feb 20–27, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $1,673 ($239/night)
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Marriott's Desert Springs Villas
Palm Desert, California- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,112 ($588/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20 – Mar 2, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $2,837 ($284/night)
The Point at Poipu
Koloa, Hawaii- Feb 20 – Mar 6, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $6,892 ($492/night)
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Voted Top Pick 2026
The Royal Sands
Cancun, Mexico- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,213 ($459/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Feb 20–27, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $4,336 ($619/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,532 ($362/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,148 ($735/night)
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Divi Dutch Village Beach Resort
Oranjestad, Aruba- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,924 ($418/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,200 ($1,171/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,840 ($549/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,891 ($984/night)
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Sunrise Lodge by Hilton Grand Vacations
Park City, Utah- Feb 20–27, 2027 (7 nights)
- 4 bed/5 bath, sleeps 10
- $7,655 ($1,094/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Inn on Long Wharf
Newport, Rhode Island- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $559 ($80/night)
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Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,886 ($412/night)
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Hacienda del Mar Resort
Cabo San Lucas, Mexico- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 6
- $5,312 ($759/night)
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Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,474 ($782/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,132 ($447/night)
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Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,233 ($890/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,544 ($1,078/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,544 ($1,078/night)
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Vacation Village at Weston
Weston, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,205 ($315/night)
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Marriott's Maui Ocean Club - Napili Tower
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,557 ($794/night)
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Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,218 ($1,031/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 20–27, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $7,655 ($1,094/night)
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Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $11,905 ($1,701/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
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The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Feb 20–27, 2027 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $12,014 ($1,716/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,711 ($387/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,513 ($502/night)
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Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,015 ($859/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,471 ($210/night)
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The Westin St. John - Coral Vista Villas
Cruz Bay, St. John (USVI)- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,928 ($1,132/night)
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CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–28, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,760 ($220/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
Club Wyndham Park City
Park City, Utah- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,233 ($1,748/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,649 ($521/night)