Winter Timeshare Rentals in Florida

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,205 ($315/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
$2,749 ($393/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,180 ($197/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)

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
$9,919 ($1,417/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
$2,096 ($299/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
$8,418 ($1,203/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 26, 2026 – Jan 3, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,641 ($330/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
$2,750 ($393/night)

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Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 26–30, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$968 ($242/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,404 ($486/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
$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
$4,603 ($658/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,590 ($265/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 4, 2027 (9 nights)
1 bed/1 bath, sleeps 4
$1,760 ($196/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
$8,636 ($1,234/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,987 ($284/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 26–30, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$826 ($206/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)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3 bath, sleeps 10
$8,308 ($1,187/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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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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Marriott's Royal Palms

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,295 ($471/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
$901 ($129/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
$6,560 ($937/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)

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
$9,726 ($1,389/night)

Verified & Protected 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)

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)

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
$7,873 ($1,125/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
$9,726 ($1,389/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
$4,004 ($572/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26–30, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,114 ($279/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)

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
$5,257 ($751/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)

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)

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)

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)

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
$9,726 ($1,389/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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (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 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$9,726 ($1,389/night)

Verified & Protected

Marriott's Royal Palms

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,290 ($470/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$4,385 ($626/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
$4,112 ($588/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
$4,957 ($708/night)