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.
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
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)
Verified & Protected
Voted Top Pick 2026
Divi Aruba Phoenix Beach Resort
Palm Beach, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $4,385 ($626/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $4,876 ($696/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 9–23, 2027 (14 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($274/night)
Verified & Protected
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 6
- $3,294 ($471/night)
Verified & Protected
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
- $7,655 ($1,094/night)
Verified & Protected
Villa del Arco Beach Resort & Spa
Cabo San Lucas, Mexico- Jan 9–16, 2027 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,866 ($267/night)
Verified & Protected
Royal Haciendas
Playa del Carmen, Mexico- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Voted Top Pick 2026
Hyatt Vacation Club at Ka'anapali Beach
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,699 ($1,528/night)
Verified & Protected
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
- $5,740 ($820/night)
Verified & Protected
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
- $5,709 ($816/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,434 ($919/night)
Verified & Protected
Grand Timber Lodge
Breckenridge, Colorado- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,042 ($292/night)
Verified & Protected
Marriott's Summit Watch
Park City, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,358 ($765/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $10,375 ($1,482/night)
Verified & Protected
Club Wyndham Santa Barbara
Pompano Beach, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 9–23, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $2,701 ($193/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 9–23, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,489 ($249/night)
Verified & Protected
The Cliff Club at Snowbird
Snowbird, Utah- Jan 9–16, 2027 (7 nights)
- 2 bed/3 bath, sleeps 10
- $7,647 ($1,092/night)
Verified & Protected
WorldMark Kihei Resort
Kihei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,096 ($299/night)
Verified & Protected
Hilton Vacation Club Cabo Azul Los Cabos
San Jose del Cabo, Mexico- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,467 ($352/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–15, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $892 ($149/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,748 ($821/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $6,510 ($930/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,181 ($454/night)
Verified & Protected
Divi Dutch Village Beach Resort
Oranjestad, Aruba- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 9–16, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,455 ($922/night)
Verified & Protected
The Westin Lagunamar Ocean Resort Villas & Spa
Cancun, Mexico- Jan 9–16, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,096 ($299/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–23, 2027 (14 nights)
- 3 bed/2 bath, sleeps 10
- $4,054 ($290/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 9–23, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,321 ($237/night)
Verified & Protected
The Banyan Resort
Key West, Florida- Jan 9–16, 2027 (7 nights)
- Studio/1 bath, sleeps 2
- $2,423 ($346/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–14, 2027 (4 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($134/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Long Wharf
Newport, Rhode Island- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $839 ($120/night)
Verified & Protected
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)
Verified & Protected
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)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,744 ($1,249/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 10–17, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,420 ($489/night)
Verified & Protected
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)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–15, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,003 ($201/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 10–17, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)