Winter Timeshare Rentals in Florida

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 5–13, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$919 ($115/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–9, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$555 ($139/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–14, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$999 ($111/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/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

Grand Beach Resort

Orlando, Florida

Dec 5–12, 2026 (7 nights)
3 bed/3 bath, sleeps 8
$1,660 ($237/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

Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 5–11, 2026 (6 nights)
Studio/1 bath, sleeps 4
$2,292 ($382/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–10, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$499 ($100/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

Blue Tree Resort at Lake Buena Vista

Orlando, Florida

Dec 5–12, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$831 ($119/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 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 CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–8, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$684 ($228/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 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 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 5–9, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$870 ($218/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

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 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 CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–9, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$427 ($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
$4,222 ($603/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 Ocean Walk

Daytona Beach, Florida

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

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–13, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,202 ($150/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 5–10, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$670 ($134/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 Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–20, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$2,345 ($167/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–10, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$746 ($186/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 CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 6–9, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$271 ($90/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

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 6–11, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,605 ($321/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

Hyatt Sunset Harbor Resort

Key West, Florida

Dec 6–10, 2026 (4 nights)
Studio/1 bath, sleeps 2
$1,330 ($332/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
$3,066 ($438/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 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

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 6–9, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$499 ($166/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 Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–13, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,568 ($510/night)

Verified & Protected

Disney's Old Key West Resort

Lake Buena Vista, Florida

Dec 6–9, 2026 (3 nights)
Studio/1 bath, sleeps 4
$1,363 ($454/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 6–13, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$746 ($107/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 Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 6–11, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$2,531 ($506/night)