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 Waiohai Beach Club
Koloa, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,402 ($914/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 8
- $5,856 ($837/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20–25, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,839 ($368/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,843 ($549/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 20–26, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $3,504 ($584/night)
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Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Feb 20–26, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,850 ($475/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/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 Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 20–27, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($626/night)
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Disney's Riviera Resort
Lake Buena Vista, Florida- Feb 20–23, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,997 ($666/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Feb 20–27, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $3,840 ($549/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Feb 20–27, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,459 ($637/night)
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Voted Top Pick 2026
The Westin Kierland Villas
Scottsdale, Arizona- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,217 ($602/night)
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Sunrise Lodge by Hilton Grand Vacations
Park City, Utah- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,058 ($580/night)
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Grand Lodge on Peak 7
Breckenridge, Colorado- 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 Desert Springs Villas II
Palm Desert, California- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20 – Mar 2, 2027 (10 nights)
- 1 bed/1 bath, sleeps 4
- $2,109 ($211/night)
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Villa del Palmar Flamingos
Nuevo Vallarta, Mexico- Feb 20–27, 2027 (7 nights)
- 2 bed/3 bath, sleeps 6
- $2,750 ($393/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20 – Mar 2, 2027 (10 nights)
- 3 bed/2 bath, sleeps 10
- $3,897 ($390/night)
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Royal Haciendas
Playa del Carmen, Mexico- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,404 ($486/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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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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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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Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Feb 20–27, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
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Marriott's Lakeshore Reserve
Orlando, Florida- Feb 20–27, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,126 ($447/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
- $10,920 ($1,560/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20 – Mar 1, 2027 (9 nights)
- 3 bed/2 bath, sleeps 10
- $3,583 ($398/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 20 – Mar 1, 2027 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,602 ($289/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 21–28, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Feb 21–28, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,412 ($630/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Feb 21–26, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,510 ($502/night)
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Voted Top Pick 2026
Marriott's OceanWatch Villas at Grande Dunes
Myrtle Beach, South Carolina- Feb 21–26, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,110 ($222/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,091 ($870/night)
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Marriott's Mountain Valley Lodge
Breckenridge, Colorado- Feb 21–26, 2027 (5 nights)
- 1 bed/2 bath, sleeps 6
- $2,287 ($457/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 21–28, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,494 ($642/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 21–25, 2027 (4 nights)
- 3 bed/2 bath, sleeps 10
- $1,277 ($319/night)
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The Westin St. John - Virgin Grand Villas
Cruz Bay, St. John (USVI)- Feb 21–28, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $7,650 ($1,093/night)
Hyatt Windward Pointe Resort
Key West, Florida- Feb 21 – Mar 6, 2027 (13 nights)
- 2 bed/2 bath, sleeps 6
- $6,543 ($503/night)
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Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Feb 21–28, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $5,328 ($761/night)
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Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Feb 21–26, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $3,660 ($732/night)
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Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,456 ($922/night)
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Marriott's Monarch at Sea Pines
Hilton Head Island, South Carolina- Feb 21–26, 2027 (5 nights)
- 2 bed/2 bath, sleeps 6
- $1,076 ($215/night)
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Hyatt Beach House Resort
Key West, Florida- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
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Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Feb 21–28, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,592 ($656/night)
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Marriott's Heritage Club
Hilton Head Island, South Carolina- Feb 21–26, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,208 ($242/night)