Winter Timeshare Rentals in Florida

Verified & Protected 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
$6,891 ($984/night)

Verified & Protected 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
$8,090 ($1,156/night)

Verified & Protected 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
$5,366 ($767/night)

Verified & Protected

Vistana Beach Club

Jensen Beach, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$4,603 ($658/night)

Verified & Protected

Westgate Lakes Resort & Spa

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,529 ($218/night)

Verified & Protected

Marriott's Lakeshore Reserve

Orlando, Florida

Dec 27, 2026 – Jan 1, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$3,622 ($724/night)

Verified & Protected 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
$9,616 ($1,374/night)

Verified & Protected 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
$8,308 ($1,187/night)

Verified & Protected 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
$6,019 ($860/night)

Verified & Protected 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
$8,744 ($1,249/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,096 ($299/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$1,987 ($284/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 27, 2026 – Jan 3, 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 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,527 ($1,218/night)

Verified & Protected

Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,260 ($323/night)

Verified & Protected 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
$4,712 ($673/night)

Verified & Protected

Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$4,688 ($670/night)

Verified & Protected 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
$5,257 ($751/night)

Verified & Protected 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
$4,930 ($704/night)

Verified & Protected

Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 5
$5,440 ($777/night)

Hyatt Sunset Harbor Resort

Key West, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 2
$3,295 ($471/night)

Verified & Protected 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
$9,181 ($1,312/night)

Verified & Protected

Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 4
$4,688 ($670/night)

Verified & Protected 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)

Verified & Protected

Marriott's Harbour Lake

Orlando, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,859 ($408/night)

Verified & Protected 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)

Verified & Protected 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
$8,527 ($1,218/night)

Verified & Protected 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
$9,181 ($1,312/night)

Verified & Protected

The Villas at Disney's Grand Floridian Resort & Spa

Lake Buena Vista, Florida

Dec 27, 2026 – Jan 3, 2027 (7 nights)
Studio/1 bath, sleeps 5
$5,473 ($782/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 27–31, 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 27–31, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$959 ($240/night)

Verified & Protected 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
$5,257 ($751/night)

Verified & Protected 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
$7,764 ($1,109/night)

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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
1 bed/1 bath, sleeps 4
$937 ($187/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 28, 2026 – Jan 4, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 28, 2026 – Jan 2, 2027 (5 nights)
2 bed/2 bath, sleeps 8
$1,295 ($259/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,418 ($1,203/night)

Verified & Protected

Marriott's Oceana Palms

Riviera Beach, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 29, 2026 – Jan 1, 2027 (3 nights)
1 bed/1 bath, sleeps 4
$1,297 ($432/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 29, 2026 – Jan 5, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$8,200 ($1,171/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 5, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,745 ($291/night)

Verified & Protected

Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 2, 2027 (3 nights)
Studio/1 bath, sleeps 5
$2,238 ($746/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 5, 2027 (6 nights)
3 bed/2 bath, sleeps 10
$1,935 ($322/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 30, 2026 – Jan 5, 2027 (6 nights)
1 bed/1 bath, sleeps 4
$1,074 ($179/night)

Marriott's Lakeshore Reserve

Orlando, Florida

Dec 30, 2026 – Jan 2, 2027 (3 nights)
2 bed/2 bath, sleeps 8
$1,987 ($662/night)

Verified & Protected

Copper Creek Villas & Cabins at Disney's Wilderness Lodge

Lake Buena Vista, Florida

Dec 31, 2026 – Jan 5, 2027 (5 nights)
Studio/1 bath, sleeps 4
$2,965 ($593/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 31, 2026 – Jan 7, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$5,358 ($765/night)