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.
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 31, 2026 – Jan 3, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $915 ($305/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $5,038 ($720/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 31, 2026 – Jan 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
Verified & Protected
Marriott's St. Kitts Beach Club
Frigate Bay, St. Kitts- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,892 ($985/night)
Verified & Protected
Voted Top Pick 2026
The Westin Nanea Ocean Villas
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $11,852 ($1,693/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Lahaina Tower
Lahaina, Hawaii- Jan 1–6, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $9,830 ($1,966/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–15, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $2,222 ($159/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,744 ($1,249/night)
Verified & Protected
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 1–3, 2027 (2 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($2,465/night)
Verified & Protected
Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,711 ($542/night)
Verified & Protected
Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 5
- $4,224 ($603/night)
Verified & Protected
Sheraton Kauai Resort Villas
Koloa, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,893 ($699/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,038 ($720/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,546 ($1,078/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Verified & Protected
The Villas at Disney's Grand Californian Hotel & Spa
Anaheim, California- Jan 1–4, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $3,622 ($1,207/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,655 ($1,094/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–7, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,860 ($310/night)
Verified & Protected
Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 1–5, 2027 (4 nights)
- Studio/1 bath, sleeps 2
- $1,554 ($389/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Grand Desert
Las Vegas, Nevada- Jan 1–4, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $906 ($302/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Newport Coast Villas
Newport Coast, California- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Verified & Protected
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 1–4, 2027 (3 nights)
- Studio/1 bath, sleeps 4
- $1,119 ($373/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,707 ($1,530/night)
Verified & Protected
Voted Top Pick 2026
Harborside Resort at Atlantis
Paradise Island, Bahamas- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,731 ($533/night)
Verified & Protected
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Jan 1–8, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $2,750 ($393/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,674 ($953/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,311 ($1,187/night)
Verified & Protected
Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 1–3, 2027 (2 nights)
- Studio/1 bath, sleeps 5
- $1,101 ($551/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,944 ($563/night)
Verified & Protected
Wyndham Vacation Resorts Royal Garden at Waikiki
Honolulu, Hawaii- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $2,478 ($496/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Aruba Ocean Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $5,366 ($767/night)
Verified & Protected
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 1–2, 2027 (1 night)
- Studio/1 bath, sleeps 4
- $613 ($613/night)
Verified & Protected
Sheraton Mountain Vista Villas
Avon, Colorado- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,832 ($547/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,294 ($471/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,928 ($1,132/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,928 ($1,132/night)
Verified & Protected
Hilton Grand Vacations Club Whistler
Whistler, British Columbia, Canada- Jan 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,295 ($471/night)
Verified & Protected
Westgate Vacation Villas
Kissimmee, Florida- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,486 ($212/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,743 ($549/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 1–6, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,712 ($542/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Great Smokies Lodge
Sevierville, Tennessee- Jan 1–4, 2027 (3 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($213/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas North
Lahaina, Hawaii- Jan 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,290 ($470/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Jan 1–3, 2027 (2 nights)
- 2 bed/2 bath, sleeps 8
- $2,150 ($1,075/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Jan 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,584 ($1,226/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 1–10, 2027 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,568 ($174/night)