Winter Timeshare Rentals in Greater Orlando

Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

Verified & Protected

Vacation Village at Parkway

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25, 2026 – Jan 3, 2027 (9 nights)
2 bed/2 bath, sleeps 8
$2,641 ($293/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25, 2026 – Jan 3, 2027 (9 nights)
1 bed/1 bath, sleeps 4
$1,917 ($213/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25–28, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$764 ($255/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25–28, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$1,030 ($343/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25–30, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,119 ($224/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25–31, 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 25, 2026 – Jan 2, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,310 ($289/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25–30, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,506 ($301/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25, 2026 – Jan 2, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$1,695 ($212/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,978 ($283/night)

Verified & Protected

Cypress Pointe Resort

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
3 bed/3 bath, sleeps 8
$1,764 ($252/night)

Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,096 ($299/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,384 ($626/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$5,420 ($774/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25–31, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,295 ($216/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,404 ($486/night)

Verified & Protected

Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,949 ($564/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/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 CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26–31, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,352 ($270/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 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 26–31, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,003 ($201/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26–31, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,128 ($226/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
$2,641 ($377/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,185 ($455/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 4, 2027 (9 nights)
1 bed/1 bath, sleeps 4
$1,760 ($196/night)

Verified & Protected

Westgate Lakes Resort & Spa

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,782 ($255/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

Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
Studio/1 bath, sleeps 5
$4,603 ($767/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 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 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
$1,922 ($275/night)

Verified & Protected

Marriott's Imperial Palm Villas

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/2 bath, sleeps 10
$3,786 ($541/night)

Verified & Protected

Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 26–31, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,932 ($386/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,277 ($213/night)

Verified & Protected

Marriott's Grande Vista

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,859 ($408/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

Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,840 ($549/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,268 ($181/night)

Verified & Protected

Marriott's Sabal Palms

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,696 ($385/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
$2,745 ($392/night)

Verified & Protected

Marriott's Lakeshore Reserve

Orlando, Florida

Dec 26–30, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$2,532 ($633/night)

Verified & Protected

Sheraton Vistana Villages

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$3,069 ($438/night)