Winter Timeshare Rentals in Florida

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 9–12, 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 9–12, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$684 ($228/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,306 ($472/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 10–17, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,622 ($517/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 10–13, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$808 ($269/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 10–13, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$535 ($178/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 10–13, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$439 ($146/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,295 ($471/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–19, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,943 ($243/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–20, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$1,660 ($184/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–20, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$2,275 ($253/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–20, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$1,778 ($198/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–20, 2026 (9 nights)
3 bed/2 bath, sleeps 10
$2,667 ($296/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–19, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,012 ($127/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–20, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,185 ($132/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 11–19, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,436 ($179/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
3 bed/2 bath, sleeps 10
$1,180 ($236/night)

Verified & Protected

Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,077 ($615/night)

DiamondHead Beach Resort

Fort Myers Beach, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,768 ($253/night)

Verified & Protected

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,314 ($331/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$586 ($117/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–20, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,330 ($148/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,749 ($393/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–19, 2026 (8 nights)
3 bed/2 bath, sleeps 10
$2,109 ($264/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–15, 2026 (4 nights)
3 bed/2 bath, sleeps 10
$995 ($249/night)

CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–14, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$599 ($200/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–16, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$764 ($153/night)

Verified & Protected

Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 11–16, 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 11–19, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,039 ($130/night)

Verified & Protected

Boulder Ridge Villas at Disney's Wilderness Lodge

Lake Buena Vista, Florida

Dec 11–17, 2026 (6 nights)
Studio/1 bath, sleeps 5
$5,473 ($912/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–18, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$1,550 ($221/night)

Eagle's Nest Beach Resort

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,813 ($545/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$746 ($107/night)

Verified & Protected

Marriott's Lakeshore Reserve

Orlando, Florida

Dec 11–17, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$2,423 ($404/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–15, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$511 ($128/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,949 ($564/night)

Verified & Protected

DiamondHead Beach Resort

Fort Myers Beach, Florida

Dec 11–18, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,123 ($303/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–15, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$648 ($162/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 11–18, 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 11–14, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$439 ($146/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 11–18, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,565 ($938/night)

Verified & Protected

Marriott Vacation Club Pulse, South Beach

Miami Beach, Florida

Dec 12–19, 2026 (7 nights)
Studio/1 bath, sleeps 3
$3,069 ($438/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,180 ($169/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 12–19, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$866 ($124/night)

Verified & Protected

The Villas at Disney's Grand Floridian Resort & Spa

Lake Buena Vista, Florida

Dec 12–18, 2026 (6 nights)
Studio/1 bath, sleeps 5
$4,381 ($730/night)

Verified & Protected

Marriott's Oceana Palms

Riviera Beach, Florida

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$6,129 ($876/night)

Verified & Protected

The Villas at Disney's Grand Floridian Resort & Spa

Lake Buena Vista, Florida

Dec 12–19, 2026 (7 nights)
Studio/1 bath, sleeps 5
$5,205 ($744/night)

Verified & Protected Voted Top Pick 2026

Marriott's Crystal Shores

Marco Island, Florida

Dec 12–19, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,458 ($494/night)