Winter Timeshare Rentals in Florida

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–30, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$870 ($174/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,611 ($516/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$979 ($163/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,821 ($689/night)

Verified & Protected Voted Top Pick 2026

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)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,693 ($813/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,042 ($292/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,023 ($718/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,949 ($564/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 10
$2,314 ($331/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,186 ($455/night)

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Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 25–28, 2026 (3 nights)
1 bed/2 bath, sleeps 5
$4,276 ($1,425/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,745 ($1,249/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,257 ($751/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$5,420 ($774/night)

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Cypress Pointe Resort

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
3 bed/3 bath, sleeps 8
$1,654 ($236/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,840 ($549/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,731 ($533/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,840 ($549/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,764 ($538/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,096 ($299/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,123 ($303/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–30, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,180 ($236/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
$1,442 ($206/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,542 ($220/night)

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Summer Bay Orlando Resort

Clermont, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,358 ($194/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,731 ($533/night)

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Palm Beach Shores Resort and Vacation Villas

Palm Beach Shores, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,704 ($243/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
$4,222 ($603/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,268 ($211/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 5
$5,801 ($829/night)

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Fort Lauderdale Beach Resort

Fort Lauderdale, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,100 ($300/night)

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Club Wyndham Palm-Aire

Pompano Beach, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,769 ($253/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,696 ($385/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,356 ($226/night)

Verified & Protected 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
$4,903 ($700/night)

Verified & Protected 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
$7,655 ($1,094/night)

Verified & Protected 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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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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Marriott's Imperial Palm Villas

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/2 bath, sleeps 10
$3,230 ($461/night)

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Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 10
$1,856 ($265/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
$3,840 ($549/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,859 ($408/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$1,871 ($267/night)