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 Cypress Palms
Kissimmee, Florida- Dec 8–12, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $626 ($157/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 8–12, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $790 ($198/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 8–15, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,127 ($161/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 8–22, 2026 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,199 ($229/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 8–22, 2026 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,365 ($98/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 8–12, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $427 ($107/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–13, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($244/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 9–14, 2026 (5 nights)
- 3 bed/3 bath, sleeps 10
- $2,750 ($550/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–13, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($128/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,119 ($160/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–14, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $852 ($170/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–14, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,128 ($226/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–12, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $639 ($213/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–12, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $499 ($166/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,840 ($549/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–16, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($107/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–12, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $355 ($118/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–16, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,427 ($204/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–14, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($117/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 9–13, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($180/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–13, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $439 ($146/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $852 ($170/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 10–16, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,436 ($239/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,260 ($609/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–15, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,128 ($226/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 10–16, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $613 ($102/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–14, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($180/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–14, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $977 ($244/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 10–17, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,191 ($456/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $826 ($275/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–15, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($117/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–14, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $511 ($128/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 10–16, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $826 ($138/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 10–13, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $586 ($195/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,119 ($160/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,031 ($576/night)
Eagle's Nest Beach Resort
Marco Island, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,068 ($438/night)
DiamondHead Beach Resort
Fort Myers Beach, Florida- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,768 ($253/night)
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 11–17, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,150 ($358/night)
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)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $862 ($172/night)
DiamondHead Beach Resort
Fort Myers Beach, Florida- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,932 ($276/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($564/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)