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 19–25, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,682 ($280/night)
Westgate Lakes Resort & Spa
Orlando, Florida- Dec 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,238 ($320/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,932 ($276/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,330 ($190/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,658 ($665/night)
Westgate Lakes Resort & Spa
Orlando, Florida- Dec 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $1,866 ($267/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 19–27, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,768 ($221/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–23, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $627 ($157/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,320 ($903/night)
Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 19–23, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $3,478 ($870/night)
Grand Seas Resort
Daytona Beach, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,009 ($287/night)
Westgate Vacation Villas
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
Sheraton Vistana Resort
Orlando, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,535 ($219/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–23, 2026 (4 nights)
- 2 bed/2 bath, sleeps 8
- $855 ($214/night)
Marriott's Grande Vista
Orlando, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,070 ($439/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,647 ($1,092/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,619 ($374/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,437 ($1,062/night)
Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 19–26, 2026 (7 nights)
- 3 bed/2 bath, sleeps 10
- $4,153 ($593/night)
Marriott's Grande Vista
Orlando, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,230 ($461/night)
Club Wyndham Palm-Aire
Pompano Beach, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,731 ($533/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,121 ($1,017/night)
Westgate Town Center
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,381 ($197/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–22, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $684 ($228/night)
Silver Lake Resort
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,123 ($303/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–22, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $507 ($169/night)
Marriott's Grande Vista
Orlando, Florida- Dec 19, 2026 – Jan 2, 2027 (14 nights)
- 3 bed/3 bath, sleeps 12
- $8,745 ($625/night)
Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,260 ($323/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,932 ($276/night)
Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 19–22, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $941 ($314/night)
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,696 ($385/night)
Vacation Village at Bonaventure
Weston, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,932 ($276/night)
Marriott's Oceana Palms
Riviera Beach, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,910 ($844/night)
Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,161 ($309/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 19–26, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $9,143 ($1,306/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($1,405/night)
Marriott's Oceana Palms
Riviera Beach, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,412 ($630/night)
Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($377/night)
Las Palmeras by Hilton Grand Vacations
Orlando, Florida- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 2
- $1,550 ($221/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 19–27, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($766/night)
Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Dec 19–26, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $1,925 ($275/night)
Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,465 ($209/night)
Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 19–24, 2026 (5 nights)
- Studio/1 bath, sleeps 4
- $2,123 ($425/night)
Marriott's Crystal Shores
Marco Island, Florida- Dec 19–27, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($821/night)
Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 19–26, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $941 ($134/night)
Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 19–26, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,230 ($461/night)