Winter Timeshare Rentals in Greater Orlando

Marriott's Grande Vista

Orlando, Florida

Dec 19, 2026 – Jan 2, 2027 (14 nights)
3 bed/3 bath, sleeps 12
$8,745 ($625/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,211 ($173/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–22, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$1,207 ($402/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

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Parc Soleil by Hilton Grand Vacations

Orlando, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$2,205 ($315/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–28, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$2,602 ($289/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–28, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$3,213 ($357/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 4
$1,705 ($341/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–28, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,935 ($215/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 19–26, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$4,603 ($658/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–23, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$1,114 ($279/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$1,003 ($201/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 19–24, 2026 (5 nights)
2 bed/2 bath, sleeps 6
$1,110 ($222/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 4
$1,778 ($356/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,240 ($463/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 2026 (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 19–29, 2026 (10 nights)
2 bed/2 bath, sleeps 8
$2,837 ($284/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$4,380 ($626/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–23, 2026 (4 nights)
1 bed/1 bath, sleeps 4
$826 ($206/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–27, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$1,760 ($220/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,440 ($206/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,240 ($463/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–27, 2026 (8 nights)
2 bed/2 bath, sleeps 8
$2,366 ($296/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 2026 (7 nights)
3 bed/2 bath, sleeps 10
$3,840 ($549/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–31, 2026 (12 nights)
2 bed/2 bath, sleeps 8
$3,308 ($276/night)

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Parc Soleil by Hilton Grand Vacations

Orlando, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$5,453 ($779/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$7,432 ($1,062/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 5
$4,191 ($838/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–22, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$875 ($292/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
Studio/1 bath, sleeps 5
$3,657 ($731/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–27, 2026 (8 nights)
1 bed/1 bath, sleeps 4
$2,366 ($296/night)

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Las Palmeras by Hilton Grand Vacations

Orlando, Florida

Dec 19–26, 2026 (7 nights)
Studio/1 bath, sleeps 2
$1,550 ($221/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19, 2026 – Jan 1, 2027 (13 nights)
1 bed/1 bath, sleeps 4
$2,632 ($202/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,198 ($171/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19, 2026 – Jan 1, 2027 (13 nights)
2 bed/2 bath, sleeps 8
$3,544 ($273/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 19–26, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,866 ($267/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–24, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$1,352 ($270/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 2026 (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 19–22, 2026 (3 nights)
1 bed/1 bath, sleeps 4
$648 ($216/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 19–26, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,978 ($283/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 19–26, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$4,031 ($576/night)

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Westgate Town Center

Kissimmee, Florida

Dec 20–27, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,110 ($159/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20, 2026 – Jan 3, 2027 (14 nights)
1 bed/1 bath, sleeps 4
$2,789 ($199/night)