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 Cypress Palms
Kissimmee, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,211 ($173/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $995 ($142/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,295 ($471/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–16, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $679 ($136/night)
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Marriott's Lakeshore Reserve
Orlando, Florida- Dec 11–17, 2026 (6 nights)
- 2 bed/2 bath, sleeps 8
- $2,423 ($404/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,612 ($230/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 11–15, 2026 (4 nights)
- 3 bed/2 bath, sleeps 10
- $995 ($249/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 11–14, 2026 (3 nights)
- 2 bed/2 bath, sleeps 8
- $535 ($178/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 11–16, 2026 (5 nights)
- Studio/1 bath, sleeps 5
- $3,077 ($615/night)
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Eagle's Nest Beach Resort
Marco Island, Florida- Dec 11–18, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,813 ($545/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 11–16, 2026 (5 nights)
- 1 bed/1 bath, sleeps 4
- $586 ($117/night)
DiamondHead Beach Resort
Fort Myers Beach, Florida- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $1,768 ($253/night)
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Disney's Beach Club Villas
Lake Buena Vista, Florida- Dec 11–16, 2026 (5 nights)
- Studio/1 bath, sleeps 5
- $3,077 ($615/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 11–14, 2026 (3 nights)
- 1 bed/1 bath, sleeps 4
- $439 ($146/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–19, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,436 ($179/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $1,312 ($262/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–20, 2026 (9 nights)
- 2 bed/2 bath, sleeps 8
- $2,275 ($253/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $764 ($153/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–20, 2026 (9 nights)
- 2 bed/2 bath, sleeps 8
- $1,660 ($184/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 11–20, 2026 (9 nights)
- 2 bed/2 bath, sleeps 8
- $1,778 ($198/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 11–20, 2026 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,330 ($148/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 11–20, 2026 (9 nights)
- 3 bed/2 bath, sleeps 10
- $2,667 ($296/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–19, 2026 (8 nights)
- 2 bed/2 bath, sleeps 8
- $1,943 ($243/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–20, 2026 (9 nights)
- 1 bed/1 bath, sleeps 4
- $1,185 ($132/night)
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Marriott's BeachPlace Towers
Fort Lauderdale, Florida- Dec 11–18, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,314 ($331/night)
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Club Wyndham Cypress Palms
Kissimmee, Florida- Dec 11–16, 2026 (5 nights)
- 2 bed/2 bath, sleeps 8
- $946 ($189/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,513 ($502/night)
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Bay Lake Tower at Disney's Contemporary Resort
Lake Buena Vista, Florida- Dec 12–16, 2026 (4 nights)
- Studio/1 bath, sleeps 4
- $2,471 ($618/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 12–19, 2026 (7 nights)
- 3 bed/3 bath, sleeps 10
- $4,380 ($626/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $1,180 ($169/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $4,385 ($626/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 12–19, 2026 (7 nights)
- 3 bed/2 bath, sleeps 10
- $1,804 ($258/night)
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Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,622 ($517/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $2,505 ($358/night)
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Marriott Vacation Club Pulse, South Beach
Miami Beach, Florida- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 3
- $3,069 ($438/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 12–16, 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 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,458 ($494/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 12–18, 2026 (6 nights)
- Studio/1 bath, sleeps 5
- $4,381 ($730/night)
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The Villas at Disney's Grand Floridian Resort & Spa
Lake Buena Vista, Florida- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 5
- $5,205 ($744/night)
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The Galleon Resort
Key West, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $4,930 ($704/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $6,129 ($876/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 12–16, 2026 (4 nights)
- 1 bed/1 bath, sleeps 4
- $555 ($139/night)
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Marriott's Lakeshore Reserve
Orlando, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2.5 bath, sleeps 8
- $5,475 ($782/night)
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Club Wyndham Bonnet Creek Resort
Lake Buena Vista, Florida- Dec 12–19, 2026 (7 nights)
- 1 bed/1 bath, sleeps 4
- $866 ($124/night)
Verified & Protected
Voted Top Pick 2026
Marriott's Crystal Shores
Marco Island, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $3,617 ($517/night)
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Marriott's Oceana Palms
Riviera Beach, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 8
- $5,475 ($782/night)
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Disney's Old Key West Resort
Lake Buena Vista, Florida- Dec 12–19, 2026 (7 nights)
- Studio/1 bath, sleeps 4
- $2,903 ($415/night)
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Voted Top Pick 2026
Marriott's Ocean Pointe
Palm Beach Shores, Florida- Dec 12–19, 2026 (7 nights)
- 2 bed/2 bath, sleeps 6
- $3,077 ($440/night)