Winter Timeshare Rentals in Florida

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$684 ($98/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,551 ($650/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$995 ($142/night)

Verified & Protected

Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,600 ($514/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–9, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$870 ($218/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$5,366 ($767/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,404 ($486/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–19, 2026 (14 nights)
3 bed/2 bath, sleeps 10
$3,087 ($220/night)

Verified & Protected Voted Top Pick 2026

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,750 ($393/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–19, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$2,161 ($154/night)

Verified & Protected

Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
Studio/1 bath, sleeps 4
$3,164 ($452/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–8, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$355 ($118/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$746 ($107/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,058 ($580/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 5–12, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$932 ($133/night)

Shell Island Beach Club

Sanibel Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,750 ($393/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 5–8, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$826 ($275/night)

Verified & Protected

The Galleon Resort

Key West, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,930 ($704/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,696 ($385/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–12, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$1,550 ($221/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–19, 2026 (13 nights)
1 bed/1 bath, sleeps 4
$1,660 ($128/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,195 ($456/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$577 ($115/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$932 ($186/night)

Verified & Protected

Hyatt Sunset Harbor Resort

Key West, Florida

Dec 6–10, 2026 (4 nights)
Studio/1 bath, sleeps 2
$1,330 ($332/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–10, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$343 ($86/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–20, 2026 (14 nights)
3 bed/2 bath, sleeps 10
$3,583 ($256/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,330 ($190/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 6–19, 2026 (13 nights)
2 bed/2 bath, sleeps 8
$2,432 ($187/night)

Verified & Protected

Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,077 ($615/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–10, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$471 ($118/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 6–9, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$639 ($213/night)

Verified & Protected

Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
Studio/1 bath, sleeps 4
$2,990 ($598/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–19, 2026 (13 nights)
3 bed/2 bath, sleeps 10
$3,025 ($233/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–12, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$786 ($131/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,929 ($704/night)

Verified & Protected

Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,077 ($615/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,290 ($470/night)

Verified & Protected

Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,022 ($604/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–9, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$367 ($122/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 6–9, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$355 ($118/night)

Verified & Protected

Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 6–11, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,022 ($604/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–12, 2026 (6 nights)
3 bed/2 bath, sleeps 10
$1,242 ($207/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–13, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$1,550 ($221/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–9, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$559 ($186/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–20, 2026 (14 nights)
1 bed/1 bath, sleeps 4
$1,725 ($123/night)