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.
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 11–17, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,207 ($201/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,062 ($437/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,519 ($788/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $862 ($172/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 11–17, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $613 ($102/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–15, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($128/night)
Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 11–17, 2026 (6 nights)
- Studio/1 bath, sleeps 5
- $5,473 ($912/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–16, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $595 ($119/night)
Casa Ybel Resort
Sanibel Island, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,657 ($380/night)
DiamondHead Beach Resort
Fort Myers Beach, Florida- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,768 ($253/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–15, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($244/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–15, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($180/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($107/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,031 ($576/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,268 ($467/night)
Ocean East Resort Club
Ormond Beach, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/1 bath, sleeps 6
- $1,550 ($221/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,562 ($1,366/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–18, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $892 ($149/night)
Marriott's Oceana Palms
Riviera Beach, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,191 ($456/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $684 ($98/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 12–18, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,251 ($208/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 12–18, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,083 ($181/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,428 ($347/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 12–18, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $733 ($122/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–18, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,092 ($182/night)
The Galleon Resort
Key West, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,748 ($821/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 12–18, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $523 ($87/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
Marriott's Oceana Palms
Riviera Beach, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,257 ($751/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,069 ($438/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
Marriott Vacation Club Pulse, South Beach
Miami Beach, Florida- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $3,069 ($438/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–17, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($188/night)
Westgate Town Center
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,458 ($494/night)
Hollywood Beach Tower
Hollywood, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/2 bath, sleeps 4
- $1,542 ($220/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,230 ($461/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,202 ($172/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,161 ($309/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,532 ($219/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–17, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $499 ($100/night)
Westgate Town Center
Kissimmee, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,358 ($194/night)
Sheraton Vistana Resort
Orlando, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,358 ($194/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 12–17, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $759 ($152/night)