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
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 7, 2027 (8 nights)
- 3 bed/2 bath, sleeps 10
- $2,436 ($305/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 30 – Feb 12, 2027 (13 nights)
- 2 bed/2 bath, sleeps 8
- $2,990 ($230/night)
Verified & Protected
Vistana Beach Club
Jensen Beach, Florida- Jan 30 – Feb 6, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 6, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $892 ($149/night)
Verified & Protected
Hyatt Beach House Resort
Key West, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $13,105 ($1,872/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 5, 2027 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,003 ($201/night)
Verified & Protected
Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 31 – Feb 1, 2027 (1 night)
- Studio/1 bath, sleeps 4
- $343 ($343/night)
Verified & Protected
Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 31 – Feb 6, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,796 ($466/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 6, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,339 ($223/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 6, 2027 (6 nights)
- 3 bed/2 bath, sleeps 10
- $1,642 ($274/night)
Hyatt Beach House Resort
Key West, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,374 ($625/night)
Hyatt Beach House Resort
Key West, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,840 ($549/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
Verified & Protected
Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 31 – Feb 1, 2027 (1 night)
- Studio/1 bath, sleeps 4
- $275 ($275/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 8, 2027 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,870 ($234/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 5, 2027 (5 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($133/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,276 ($611/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 5, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,242 ($248/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 7, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 31 – Feb 4, 2027 (4 nights)
- 2 bed/2 bath, sleeps 8
- $804 ($201/night)
Verified & Protected
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Feb 1–5, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $2,026 ($507/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,765 ($252/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Feb 1–8, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,077 ($440/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,119 ($160/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 1–8, 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- Feb 1–8, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Feb 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $932 ($133/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 1–5, 2027 (4 nights)
- 3 bed/3 bath, sleeps 10
- $3,294 ($823/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,437 ($1,062/night)
Verified & Protected
Marriott's Lakeshore Reserve
Orlando, Florida- Feb 1–7, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($531/night)
Verified & Protected
Marriott's Oceana Palms
Riviera Beach, Florida- Feb 1–11, 2027 (10 nights)
- 2 bed/2 bath, sleeps 8
- $5,464 ($546/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Feb 1–15, 2027 (14 nights)
- 1 bed/1 bath, sleeps 4
- $1,527 ($109/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Feb 1–15, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,214 ($230/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Feb 1–15, 2027 (14 nights)
- 2 bed/2 bath, sleeps 8
- $3,551 ($254/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Feb 1–8, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $746 ($107/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Feb 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Feb 1–8, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,734 ($248/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Feb 1–7, 2027 (6 nights)
- 3 bed/3 bath, sleeps 10
- $6,565 ($1,094/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 2–7, 2027 (5 nights)
- 3 bed/2 bath, sleeps 10
- $1,550 ($310/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 2–9, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Feb 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,673 ($239/night)