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
Club Wyndham Smoky Mountains
Sevierville, Tennessee- Dec 1–8, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $684 ($98/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 1–7, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,299 ($217/night)
Verified & Protected
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 1–6, 2026 (5 nights)
- 2 bed/3 bath, sleeps 10
- $5,470 ($1,094/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 1–5, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $937 ($234/night)
Verified & Protected
Garza Blanca Resort & Spa Cancun
Cancun, Mexico- Dec 1–10, 2026 (9 nights)
- 2 bed/2 bath, sleeps 6
- $10,707 ($1,190/night)
Verified & Protected
Marriott's Summit Watch
Park City, Utah- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
Verified & Protected
Marriott's Grand Residence Club, Mayfair-London
London, England- Dec 1–8, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $6,510 ($930/night)
Verified & Protected
The Westin Los Cabos Resort Villas & Spa
San Jose del Cabo, Mexico- Dec 1–6, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $1,927 ($385/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 1–6, 2026 (5 nights)
- 4 bed/4 bath, sleeps 10
- $8,690 ($1,738/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 1–5, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $706 ($176/night)
Marriott's StreamSide at Vail - Birch, Douglas, and Evergreen
Vail, Colorado- Dec 1–6, 2026 (5 nights)
- 1 bed/2 bath, sleeps 6
- $5,470 ($1,094/night)
Verified & Protected
Voted Top Pick 2026
Marriott's MountainSide at Park City
Park City, Utah- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Verified & Protected
Voted Top Pick 2026
Pueblo Bonito Sunset Beach Resort & Spa
Cabo San Lucas, Mexico- Dec 1–8, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,550 ($221/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,669 ($953/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Maui Ocean Club - Molokai, Maui & Lanai Towers
Lahaina, Hawaii- Dec 1–8, 2026 (7 nights)
- 2 bed/3 bath, sleeps 8
- $5,911 ($844/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 1–8, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,489 ($1,498/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 1–5, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($1,096/night)
Verified & Protected
Montecristo Estates by Pueblo Bonito
Cabo San Lucas, Mexico- Dec 1–8, 2026 (7 nights)
- 3 bed/3.5 bath, sleeps 10
- $3,069 ($438/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 1–7, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,488 ($248/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 1–4, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $367 ($122/night)
Verified & Protected
Novaispania Residences by Pueblo Bonito
Cabo San Lucas, Mexico- Dec 1–8, 2026 (7 nights)
- 4 bed/4.5 bath, sleeps 12
- $10,867 ($1,552/night)
Verified & Protected
WorldMark Marina Dunes
Marina, California- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Verified & Protected
Club Wyndham Smoky Mountains
Sevierville, Tennessee- Dec 1–8, 2026 (7 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($221/night)
Verified & Protected
Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 1–6, 2026 (5 nights)
- Studio/1 bath, sleeps 2
- $3,290 ($658/night)
Verified & Protected
West 57th Street by Hilton Club
New York City, New York- Dec 1–5, 2026 (4 nights)
- Studio/1 bath, sleeps 2
- $1,440 ($360/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 1–4, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $271 ($90/night)
Verified & Protected
The Ritz-Carlton Club, Vail
Vail, Colorado- Dec 1–8, 2026 (7 nights)
- 3 bed/3.5 bath, sleeps 8
- $10,707 ($1,530/night)
Verified & Protected
Voted #1 Resort 2026
Marriott's Aruba Surf Club
Palm Beach, Aruba- Dec 1–8, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,967 ($424/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,874 ($839/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,458 ($494/night)
Verified & Protected
Club Wyndham Avenue Plaza
New Orleans, Louisiana- Dec 1–4, 2026 (3 nights)
- Studio/1 bath, sleeps 2
- $367 ($122/night)
Verified & Protected
Sheraton Steamboat Resort Villas
Steamboat Springs, Colorado- Dec 1–6, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $4,380 ($876/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 1–9, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($480/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 1–7, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $852 ($142/night)
Verified & Protected
Pueblo Bonito Rose Spa & Resort
Cabo San Lucas, Mexico- Dec 1–8, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,109 ($158/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 1–8, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $2,641 ($377/night)
Verified & Protected
Aulani, a Disney Resort & Spa
Kapolei, Hawaii- Dec 1–7, 2026 (6 nights)
- Studio/1 bath, sleeps 4
- $2,804 ($467/night)
Verified & Protected
Voted Top Pick 2026
The Westin Kaanapali Ocean Resort Villas
Lahaina, Hawaii- Dec 1–6, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,423 ($485/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 1–6, 2026 (5 nights)
- 3 bed/3 bath, sleeps 10
- $2,750 ($550/night)
Verified & Protected
Club Wyndham Bali Hai Villas
Princeville, Hawaii- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,295 ($471/night)
Verified & Protected
Club Wyndham Avenue Plaza
New Orleans, Louisiana- Dec 1–4, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $415 ($138/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 1–5, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $499 ($125/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 1–7, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $639 ($107/night)
Verified & Protected
The Ritz-Carlton Club, St. Thomas
East End, St. Thomas (USVI)- Dec 1–6, 2026 (5 nights)
- 2 bed/2.5 bath, sleeps 6
- $4,112 ($822/night)
Verified & Protected
Disney's Riviera Resort
Lake Buena Vista, Florida- Dec 1–2, 2026 (1 night)
- Studio/1 bath, sleeps 5
- $622 ($622/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ko Olina Beach Club
Kapolei, Hawaii- Dec 1–7, 2026 (6 nights)
- 3 bed/3 bath, sleeps 10
- $7,862 ($1,310/night)
Verified & Protected
Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Dec 1–5, 2026 (4 nights)
- 1 bed/1 bath, sleeps 5
- $7,010 ($1,752/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Waiohai Beach Club
Koloa, Hawaii- Dec 1–8, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,671 ($810/night)