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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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,745 ($1,249/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $4,380 ($626/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,565 ($938/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $866 ($124/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 26–29, 2026 (3 nights)
- Studio/1 bath, sleeps 5
- $2,100 ($700/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,080 ($1,154/night)
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Holiday Inn Club Vacations at Orange Lake Resort - River Island
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,641 ($377/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $653 ($93/night)
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Marriott's Imperial Palm Villas
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/2 bath, sleeps 10
- $4,058 ($580/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $3,622 ($517/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,440 ($206/night)
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Westgate Lakes Resort & Spa
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $1,891 ($270/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,750 ($393/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26–29, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $648 ($216/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,922 ($275/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $2,745 ($392/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,963 ($709/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,405 ($201/night)
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Holiday Inn Club Vacations Panama City Beach Resort
Panama City Beach, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,165 ($166/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,726 ($1,389/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $10,920 ($1,560/night)
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Hyatt Vacation Club At Coconut Cove
Bonita Springs, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,222 ($603/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,726 ($1,389/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 26–30, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $427 ($107/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/3 bath, sleeps 10
- $10,162 ($1,452/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,458 ($208/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
Holiday Inn Club Vacations Marco Island - Sunset Cove Resort
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 3 bed/2 bath, sleeps 8
- $3,894 ($556/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,726 ($1,389/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,181 ($1,312/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $9,726 ($1,389/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 26–30, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $555 ($139/night)
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Disney's BoardWalk Villas
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 1, 2027 (6 nights)
- Studio/1 bath, sleeps 5
- $4,800 ($800/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 26, 2026 – Jan 3, 2027 (8 nights)
- 1 bed/1 bath, sleeps 4
- $1,629 ($204/night)
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Marriott's Cypress Harbour Villas
Orlando, Florida- Dec 26, 2026 – Jan 2, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,290 ($470/night)
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Disney's Saratoga Springs Resort & Spa
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- Studio/1 bath, sleeps 4
- $3,262 ($466/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,077 ($440/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $8,723 ($1,246/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,147 ($735/night)
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Hyatt Beach House Resort
Key West, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 6
- $5,039 ($720/night)
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Holiday Inn Club Vacations at Orange Lake Resort - West Village
Kissimmee, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,186 ($455/night)
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Club Wyndham Ocean Walk
Daytona Beach, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,334 ($191/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 27, 2026 – Jan 2, 2027 (6 nights)
- 1 bed/1 bath, sleeps 4
- $1,114 ($186/night)
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Marriott's Grande Vista
Orlando, Florida- Dec 27, 2026 – Jan 3, 2027 (7 nights)
- 3 bed/3 bath, sleeps 12
- $4,112 ($588/night)