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 23–27, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $737 ($184/night)
Boulder Ridge Villas at Disney's Wilderness Lodge
Lake Buena Vista, Florida- Dec 23–28, 2026 (5 nights)
- Studio/1 bath, sleeps 5
- $3,568 ($714/night)
Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 23–27, 2026 (4 nights)
- Studio/1 bath, sleeps 5
- $3,077 ($769/night)
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 23–30, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $4,489 ($641/night)
Disney's Riviera Resort
Lake Buena Vista, Florida- Dec 23–31, 2026 (8 nights)
- Studio/1 bath, sleeps 5
- $8,118 ($1,015/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 23–30, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($412/night)
Marriott's Grande Vista
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,688 ($384/night)
Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 24–25, 2026 (1 night)
- Studio/1 bath, sleeps 4
- $517 ($517/night)
Marriott's Oceana Palms
Riviera Beach, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,908 ($844/night)
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 24–26, 2026 (2 nights)
- Studio/1 bath, sleeps 5
- $3,108 ($1,554/night)
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 24–25, 2026 (1 night)
- Studio/1 bath, sleeps 4
- $606 ($606/night)
Hyatt Sunset Harbor Resort
Key West, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2.5 bath, sleeps 6
- $1,878 ($626/night)
Disney's Polynesian Villas & Bungalows
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- Studio/1 bath, sleeps 5
- $3,347 ($1,116/night)
Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 24–26, 2026 (2 nights)
- Studio/1 bath, sleeps 4
- $1,123 ($562/night)
Disney's Riviera Resort
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- Studio/1 bath, sleeps 2
- $2,491 ($830/night)
Marriott's Harbour Lake
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 24–27, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $604 ($201/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,944 ($1,421/night)
The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- Studio/1 bath, sleeps 5
- $3,132 ($1,044/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24–29, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $2,478 ($496/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($553/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 24–27, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $790 ($263/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,718 ($1,245/night)
Marriott's Royal Palms
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $11,470 ($1,639/night)
Marriott's Grande Vista
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,696 ($385/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 24–29, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $1,380 ($276/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $12,996 ($1,857/night)
Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- Studio/1 bath, sleeps 5
- $2,804 ($935/night)
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 24–27, 2026 (3 nights)
- Studio/1 bath, sleeps 4
- $2,804 ($935/night)
Marriott's Royal Palms
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,505 ($358/night)
Marriott's Grande Vista
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,238 ($320/night)
Marriott's Lakeshore Reserve
Orlando, Florida- Dec 24–31, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($412/night)
Sheraton Vistana Villages
Orlando, Florida- Dec 24–26, 2026 (2 nights)
- 1 bed/1 bath, sleeps 4
- $666 ($333/night)
Club Wyndham Santa Barbara
Pompano Beach, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/2 bath, sleeps 6
- $1,724 ($246/night)
Hurricane House
Sanibel Island, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,328 ($761/night)
Sheraton Vistana Villages
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
Westgate Vacation Villas
Kissimmee, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 10
- $2,314 ($331/night)
Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 25–30, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $3,290 ($658/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
Cypress Pointe Resort
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 3 bed/3 bath, sleeps 8
- $1,157 ($165/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,467 ($638/night)
Hilton Grand Vacations at McAlpin-Ocean Plaza
Miami Beach, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,649 ($521/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,565 ($652/night)
Marriott's Grande Vista
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,123 ($303/night)
Club Wyndham Santa Barbara
Pompano Beach, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,688 ($384/night)
Sheraton Vistana Villages
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($276/night)
Sheraton Vistana Resort
Orlando, Florida- Dec 25, 2026 – Jan 1, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,396 ($199/night)