Winter Timeshare Rentals in Greater Orlando

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Club Wyndham Cypress Palms

Kissimmee, Florida

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

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Club Wyndham Cypress Palms

Kissimmee, Florida

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

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Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,069 ($581/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,924 ($418/night)

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Westgate Vacation Villas

Kissimmee, Florida

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

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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
$2,886 ($412/night)

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Sheraton Vistana Resort

Orlando, Florida

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

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Vacation Village at Parkway

Kissimmee, Florida

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

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Marriott's Grande Vista

Orlando, Florida

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

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Cypress Pointe Resort

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
3 bed/3 bath, sleeps 8
$1,654 ($236/night)

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Sheraton Vistana Resort

Orlando, Florida

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

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Sheraton Vistana Villages

Orlando, Florida

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

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$979 ($163/night)

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Marriott's Grande Vista

Orlando, Florida

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

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Sheraton Vistana Villages

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,365 ($228/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

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

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Westgate Town Center

Kissimmee, Florida

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

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Marriott's Grande Vista

Orlando, Florida

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

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Sheraton Vistana Resort

Orlando, Florida

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

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 25–31, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,874 ($312/night)

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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)

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Club Wyndham Cypress Palms

Kissimmee, Florida

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

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Club Wyndham Cypress Palms

Kissimmee, Florida

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

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 3, 2027 (8 nights)
1 bed/1 bath, sleeps 4
$1,299 ($162/night)

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Summer Bay Orlando Resort

Clermont, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,358 ($194/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

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

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Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,769 ($253/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26–31, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,057 ($211/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 3, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$1,804 ($225/night)

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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)

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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)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 26, 2026 – Jan 3, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,641 ($330/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26–31, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,436 ($287/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$4,494 ($642/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$2,696 ($385/night)

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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)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Dec 26–28, 2026 (2 nights)
Studio/1 bath, sleeps 5
$1,824 ($912/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
Studio/1 bath, sleeps 5
$4,269 ($712/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,542 ($220/night)

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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
$1,550 ($221/night)

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Hilton Grand Vacations at SeaWorld

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,314 ($331/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$3,077 ($440/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,665 ($238/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$1,434 ($205/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$4,222 ($603/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
3 bed/3 bath, sleeps 12
$1,871 ($267/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26–31, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$768 ($154/night)