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.
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,114 ($186/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,550 ($221/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $8,418 ($1,203/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–24, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $710 ($178/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,894 ($271/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Dec 20–27, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,238 ($320/night)
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Hyatt Sunset Harbor Resort
Key West, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,565 ($652/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Holiday Inn Club Vacations Cape Canaveral Beach Resort
Cape Canaveral, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,930 ($704/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,519 ($217/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,076 ($297/night)
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Palm Beach Shores Resort and Vacation Villas
Palm Beach Shores, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 5
- $1,932 ($276/night)
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Holiday Inn Club Vacations Cape Canaveral Beach Resort
Cape Canaveral, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,385 ($626/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–23, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $719 ($240/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Dec 20, 2026 – Jan 3, 2027 (14 nights)
- 2 bed/2 bath, sleeps 6
- $6,456 ($461/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,476 ($211/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,802 ($829/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,886 ($412/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,772 ($396/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–23, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $535 ($178/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 20–26, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $531 ($88/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 20–26, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $741 ($124/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,986 ($284/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,693 ($813/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $7,110 ($1,016/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
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Disney's Animal Kingdom Villas - Kidani Village
Lake Buena Vista, Florida- Dec 20–24, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $2,397 ($599/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–26, 2026 (6 nights)
- 1 bed/1 bath, sleeps 4
- $901 ($150/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,682 ($280/night)
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Hyatt Windward Pointe Resort
Key West, Florida- Dec 20–24, 2026 (4 nights)
- 2 bed/2 bath, sleeps 6
- $1,878 ($470/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,020 ($860/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 9
- $6,782 ($969/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,384 ($626/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–26, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $1,587 ($265/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,022 ($432/night)
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Holiday Inn Club Vacations at Orange Lake Resort - North Village
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $3,840 ($549/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 20–27, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $702 ($100/night)
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Sheraton Vistana Resort
Orlando, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $2,423 ($346/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,053 ($865/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 20–23, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $719 ($240/night)
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Holiday Inn Club Vacations Cape Canaveral Beach Resort
Cape Canaveral, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,390 ($341/night)
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Holiday Inn Club Vacations Cape Canaveral Beach Resort
Cape Canaveral, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,858 ($408/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 20–27, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,603 ($658/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 20–27, 2026 (7 nights)
- 3 bed/3 bath, sleeps 12
- $2,586 ($370/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 20–30, 2026 (10 nights)
- 2 bed/2 bath, sleeps 8
- $9,835 ($984/night)