Winter Timeshare Rentals in Greater Orlando

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–28, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,978 ($283/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–28, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,352 ($270/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–24, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$719 ($240/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–29, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,214 ($277/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–24, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$719 ($240/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–31, 2026 (10 nights)
2 bed/2 bath, sleeps 8
$2,685 ($268/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$499 ($100/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$759 ($152/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$941 ($188/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 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 21–27, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,743 ($290/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 21–26, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,605 ($321/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–24, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$535 ($178/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–25, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$710 ($178/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,978 ($283/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–29, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$839 ($120/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–25, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$535 ($178/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–25, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$719 ($240/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–26, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,114 ($279/night)

Verified & Protected

Holiday Inn Club Vacations Orlando Breeze Resort

Davenport, Florida

Dec 22–29, 2026 (7 nights)
3 bed/3 bath, sleeps 10
$6,020 ($860/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–26, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,114 ($279/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–28, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,743 ($290/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–27, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,506 ($301/night)

Verified & Protected

Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 22–24, 2026 (2 nights)
Studio/1 bath, sleeps 5
$1,026 ($513/night)

Verified & Protected

Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 22–29, 2026 (7 nights)
3 bed/4 bath, sleeps 12
$13,105 ($1,872/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–26, 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 22–30, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,647 ($206/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–30, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,214 ($277/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–28, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,295 ($216/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–31, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$2,449 ($272/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 22, 2026 – Jan 3, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$3,256 ($271/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–25, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$719 ($240/night)

Verified & Protected

Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,505 ($358/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–31, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,821 ($202/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,612 ($230/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–29, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–27, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,506 ($301/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 22–27, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,119 ($224/night)

Verified & Protected

Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 22–26, 2026 (4 nights)
Studio/1 bath, sleeps 4
$3,077 ($769/night)

Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

Dec 22–30, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,192 ($149/night)

Verified & Protected

Disney's Animal Kingdom Villas - Kidani Village

Lake Buena Vista, Florida

Dec 23–26, 2026 (3 nights)
Studio/1 bath, sleeps 4
$1,830 ($610/night)

Verified & Protected

Disney's Riviera Resort

Lake Buena Vista, Florida

Dec 23–31, 2026 (8 nights)
Studio/1 bath, sleeps 5
$8,118 ($1,015/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–30, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–29, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,295 ($216/night)

Verified & Protected

Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 23–29, 2026 (6 nights)
Studio/1 bath, sleeps 5
$4,930 ($822/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 23–30, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,978 ($283/night)