RedWeek

Destinations
Featured
Christmas Timeshare Rentals

Christmas Timeshare Rentals

Celebrated each year on December 25, Christmas is the time for family traditions and festive travel. With schools and many businesses closed between Christmas Eve and New Year’s Day, the holiday season is perfect for a getaway - whether you’re dreaming of a snowy winter wonderland at a ski resort or a sunny beach Christmas with your loved ones!

Sort by:

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23, 2026 – Jan 4, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$3,561 ($297/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23, 2026 – Jan 4, 2027 (12 nights)
1 bed/1 bath, sleeps 4
$1,900 ($158/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 23, 2026 – Jan 4, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$2,632 ($219/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,886 ($412/night)

Verified & Protected

Westgate Town Center

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$2,619 ($374/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,085 ($298/night)

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

Verified & Protected

Westgate Vacation Villas

Kissimmee, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 10
$2,314 ($331/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–30, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$1,734 ($217/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–30, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,268 ($159/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22–30, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,362 ($295/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–30, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,629 ($326/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–30, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$870 ($174/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–30, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,180 ($236/night)

Verified & Protected

Sheraton Vistana Villages

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,772 ($396/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24, 2026 – Jan 1, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,362 ($295/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24, 2026 – Jan 1, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$1,268 ($159/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24, 2026 – Jan 1, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$1,734 ($217/night)

Verified & Protected

Hilton Grand Vacations at SeaWorld

Orlando, Florida

Dec 21–28, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,696 ($385/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–29, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,180 ($236/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–29, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$870 ($174/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–29, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,629 ($326/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,276 ($325/night)

Verified & Protected

Westgate Lakes Resort & Spa

Orlando, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,550 ($221/night)

Verified & Protected

Bay Lake Tower at Disney's Contemporary Resort

Lake Buena Vista, Florida

Dec 25–28, 2026 (3 nights)
1 bed/2 bath, sleeps 5
$4,276 ($1,425/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21, 2026 – Jan 1, 2027 (11 nights)
2 bed/2 bath, sleeps 8
$3,094 ($281/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21, 2026 – Jan 1, 2027 (11 nights)
1 bed/1 bath, sleeps 4
$1,664 ($151/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 21, 2026 – Jan 1, 2027 (11 nights)
2 bed/2 bath, sleeps 8
$2,283 ($208/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20, 2026 – Jan 1, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$2,467 ($206/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20, 2026 – Jan 1, 2027 (12 nights)
1 bed/1 bath, sleeps 4
$1,795 ($150/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20, 2026 – Jan 1, 2027 (12 nights)
2 bed/2 bath, sleeps 8
$3,339 ($278/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,497 ($500/night)

Verified & Protected

Parc Soleil by Hilton Grand Vacations

Orlando, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$4,603 ($658/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,986 ($284/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–26, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,587 ($265/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,024 ($432/night)

Verified & Protected

Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 23, 2026 – Jan 1, 2027 (9 nights)
2 bed/2 bath, sleeps 8
$1,764 ($196/night)

Verified & Protected CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,963 ($423/night)

Verified & Protected

Marriott's Lakeshore Reserve

Orlando, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,001 ($429/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–30, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,874 ($312/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–30, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,003 ($167/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 24–30, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,365 ($228/night)

Verified & Protected

Hilton Grand Vacations at Tuscany Village

Orlando, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,204 ($315/night)

Verified & Protected

Sheraton Vistana Resort

Orlando, Florida

Dec 20–27, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,423 ($346/night)

Verified & Protected

Silver Lake Resort

Kissimmee, Florida

Dec 22–29, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,314 ($331/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22, 2026 – Jan 2, 2027 (11 nights)
2 bed/2 bath, sleeps 8
$2,379 ($216/night)

Verified & Protected

Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 22, 2026 – Jan 2, 2027 (11 nights)
2 bed/2 bath, sleeps 8
$3,230 ($294/night)