Winter Timeshare Rentals in Florida

Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26–31, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,003 ($201/night)

Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,641 ($377/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 26–30, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$555 ($139/night)

Verified & Protected CHOOSE YOUR OWN DATES

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)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 3, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,253 ($282/night)

Verified & Protected

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)

Verified & Protected CHOOSE YOUR OWN DATES

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

Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
Studio/1 bath, sleeps 5
$4,800 ($800/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26–30, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$826 ($206/night)

Verified & Protected CHOOSE YOUR OWN DATES

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)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26–31, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$586 ($117/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 26–30, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$888 ($222/night)

Verified & Protected

Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/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
$7,731 ($1,104/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
$8,502 ($1,215/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)

Verified & Protected

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 Ocean Pointe

Palm Beach Shores, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$3,568 ($510/night)

Verified & Protected

Boulder Ridge Villas at Disney's Wilderness Lodge

Lake Buena Vista, Florida

Dec 26–28, 2026 (2 nights)
Studio/1 bath, sleeps 5
$1,495 ($748/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
$8,309 ($1,187/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26–29, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$875 ($292/night)

Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,949 ($564/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
$8,502 ($1,215/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
$4,984 ($712/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
$5,693 ($813/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
$6,020 ($860/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 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 Ocean Pointe

Palm Beach Shores, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,739 ($677/night)

Verified & Protected

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

Discovery Beach Resort

Cocoa Beach, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,932 ($276/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,290 ($470/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,188 ($455/night)

Verified & Protected

Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 26–29, 2026 (3 nights)
Studio/1 bath, sleeps 5
$2,100 ($700/night)

Verified & Protected

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

Marriott's Grande Vista

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$4,603 ($658/night)

Verified & Protected

Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
Studio/1 bath, sleeps 4
$2,260 ($323/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26–29, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$648 ($216/night)

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
$2,183 ($312/night)

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)

Verified & Protected

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)

Verified & Protected

Hilton Grand Vacations at SeaWorld

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,641 ($377/night)

Verified & Protected

Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/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)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Ocean Walk

Daytona Beach, Florida

Dec 26–30, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$427 ($107/night)

Verified & Protected CHOOSE YOUR OWN DATES

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)

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)