Winter Timeshare Rentals in Greater Orlando

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24, 2026 – Jan 1, 2027 (8 nights)
2 bed/2 bath, sleeps 8
$2,214 ($277/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24, 2026 – Jan 2, 2027 (9 nights)
2 bed/2 bath, sleeps 8
$2,545 ($283/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 24–31, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,022 ($432/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–27, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$764 ($255/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–27, 2026 (3 nights)
2 bed/2 bath, sleeps 8
$1,030 ($343/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–27, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$1,030 ($343/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 24–31, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,471 ($210/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 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)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

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

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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)

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Marriott's Grande Vista

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$4,112 ($588/night)

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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)

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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)

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Marriott's Grande Vista

Orlando, Florida

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

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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)

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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)

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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
$3,077 ($440/night)

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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)

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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)

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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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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)

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Cypress Pointe Resort

Orlando, Florida

Dec 25, 2026 – Jan 1, 2027 (7 nights)
3 bed/3 bath, sleeps 8
$1,873 ($268/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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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)

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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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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)

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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)

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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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
1 bed/1 bath, sleeps 4
$866 ($124/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/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
$2,750 ($393/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$2,886 ($412/night)

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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)

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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)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

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

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Club Wyndham Cypress Palms

Kissimmee, Florida

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

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Marriott's Royal Palms

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$3,290 ($470/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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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 26, 2026 – Jan 1, 2027 (6 nights)
2 bed/2 bath, sleeps 8
$1,590 ($265/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
$2,641 ($377/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 6
$1,891 ($270/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
$2,641 ($377/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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Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2026 – Jan 2, 2027 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Marriott's Grande Vista

Orlando, Florida

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

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Club Wyndham Cypress Palms

Kissimmee, Florida

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