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 Cypress Palms
Kissimmee, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,581 ($226/night)
Verified & Protected
Club Wyndham Cypress Palms
Kissimmee, Florida- Jan 2–9, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,242 ($177/night)
Verified & Protected
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,711 ($542/night)
Verified & Protected
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Jan 2–6, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $1,887 ($472/night)
Verified & Protected
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 2–6, 2027 (4 nights)
- Studio/1 bath, sleeps 5
- $2,347 ($587/night)
Verified & Protected
Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 2–9, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($415/night)
Verified & Protected
Disney's Beach Club Villas
Lake Buena Vista, Florida- Jan 2–7, 2027 (5 nights)
- Studio/1 bath, sleeps 5
- $2,345 ($469/night)
Verified & Protected
Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 3–7, 2027 (4 nights)
- Studio/1 bath, sleeps 4
- $1,277 ($319/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–16, 2027 (13 nights)
- 2 bed/2 bath, sleeps 6
- $3,657 ($281/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–9, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $487 ($81/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–9, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $693 ($115/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,145 ($191/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 3–9, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($322/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,172 ($195/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,821 ($304/night)
Verified & Protected
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 1 bed/1 bath, sleeps 5
- $3,077 ($513/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–16, 2027 (13 nights)
- 3 bed/2 bath, sleeps 10
- $3,657 ($281/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–8, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $3,404 ($681/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–16, 2027 (13 nights)
- 2 bed/2 bath, sleeps 8
- $3,949 ($304/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–16, 2027 (13 nights)
- 1 bed/1 bath, sleeps 4
- $2,000 ($154/night)
Verified & Protected
Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 3–8, 2027 (5 nights)
- Studio/1 bath, sleeps 4
- $1,594 ($319/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–16, 2027 (13 nights)
- 1 bed/1 bath, sleeps 4
- $1,497 ($115/night)
Verified & Protected
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Jan 3–5, 2027 (2 nights)
- Studio/1 bath, sleeps 4
- $1,154 ($577/night)
Verified & Protected
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,581 ($527/night)
Verified & Protected
Disney's Riviera Resort
Lake Buena Vista, Florida- Jan 3–6, 2027 (3 nights)
- Studio/1 bath, sleeps 5
- $1,909 ($636/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,984 ($712/night)
Verified & Protected
Disney's Old Key West Resort
Lake Buena Vista, Florida- Jan 3–10, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $2,321 ($332/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–10, 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 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,153 ($308/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,797 ($828/night)
Verified & Protected
Disney's Animal Kingdom Villas - Jambo House
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $1,961 ($327/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–10, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $2,039 ($291/night)
Verified & Protected
Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- Studio/1 bath, sleeps 4
- $2,275 ($379/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–16, 2027 (13 nights)
- 2 bed/2 bath, sleeps 8
- $2,462 ($189/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–16, 2027 (13 nights)
- 2 bed/2 bath, sleeps 8
- $2,519 ($194/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–8, 2027 (5 nights)
- 3 bed/3 bath, sleeps 10
- $4,380 ($876/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $559 ($80/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $808 ($115/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–10, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,673 ($239/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,334 ($191/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Ocean Walk
Daytona Beach, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,365 ($195/night)
Verified & Protected
Marriott's Harbour Lake
Orlando, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,769 ($253/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,213 ($745/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–9, 2027 (6 nights)
- 2 bed/2 bath, sleeps 6
- $1,642 ($274/night)
Verified & Protected
CHOOSE YOUR OWN DATES
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Jan 3–10, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,039 ($291/night)