Winter Rentals in Greater Orlando

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Marriott's Grande Vista

Orlando, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,750 ($393/night)

Marriott's Grande Vista

Orlando, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
Studio/1 bath, sleeps 4
$1,198 ($171/night)

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Westgate Town Center

Kissimmee, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 27–31, 2025 (4 nights)
1 bed/1 bath, sleeps 4
$1,110 ($278/night)

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The Fountains

Orlando, Florida

Dec 27, 2025 – Jan 3, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,768 ($253/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$2,314 ($331/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 28, 2025 – Jan 2, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$451 ($90/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 10
$1,932 ($276/night)

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WorldMark Orlando Kingstown Reef

Orlando, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,528 ($218/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/night)

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WorldMark Orlando Kingstown Reef

Orlando, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,528 ($218/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,769 ($253/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,497 ($214/night)

Westgate Vacation Villas

Kissimmee, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 10
$1,725 ($246/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 28, 2025 – Jan 2, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$722 ($144/night)

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Vacation Village at Parkway

Kissimmee, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$888 ($127/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 28, 2025 – Jan 2, 2026 (5 nights)
2 bed/2 bath, sleeps 8
$956 ($191/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 28, 2025 – Jan 4, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,009 ($287/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 29, 2025 – Jan 2, 2026 (4 nights)
Studio/1 bath, sleeps 4
$1,550 ($388/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 29, 2025 – Jan 4, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,550 ($258/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 29, 2025 – Jan 5, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,205 ($315/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 29, 2025 – Jan 5, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,095 ($299/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 30, 2025 – Jan 5, 2026 (6 nights)
2 bed/2 bath, sleeps 8
$1,660 ($277/night)

Copper Creek Villas & Cabins at Disney's Wilderness Lodge

Lake Buena Vista, Florida

Dec 30–31, 2025 (1 night)
1 bed/1 bath, sleeps 4
$455 ($455/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 30, 2025 – Jan 6, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,123 ($303/night)

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Westgate Leisure Resort

Orlando, Florida

Dec 30, 2025 – Jan 3, 2026 (4 nights)
2 bed/2 bath, sleeps 6
$1,110 ($278/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 30, 2025 – Jan 4, 2026 (5 nights)
1 bed/1 bath, sleeps 4
$888 ($178/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 30, 2025 – Jan 6, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,440 ($206/night)

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Summer Bay Orlando Resort

Clermont, Florida

Dec 31, 2025 – Jan 6, 2026 (6 nights)
1 bed/1 bath, sleeps 4
$1,112 ($185/night)

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Marriott's Imperial Palm Villas

Orlando, Florida

Dec 31, 2025 – Jan 3, 2026 (3 nights)
3 bed/2 bath, sleeps 10
$583 ($194/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 31, 2025 – Jan 7, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,987 ($284/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 31, 2025 – Jan 4, 2026 (4 nights)
2 bed/2 bath, sleeps 8
$1,638 ($410/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Jan 1–8, 2026 (7 nights)
Studio/1 bath, sleeps 4
$888 ($127/night)

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Marriott's Sabal Palms

Orlando, Florida

Jan 1–4, 2026 (3 nights)
2 bed/2 bath, sleeps 6
$666 ($222/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Jan 2–9, 2026 (7 nights)
5 bed/5 bath, sleeps 18
$2,488 ($355/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Jan 2–9, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,789 ($256/night)

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Westgate Vacation Villas

Kissimmee, Florida

Jan 2–9, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,411 ($202/night)

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Sheraton Vistana Villages

Orlando, Florida

Jan 2–7, 2026 (5 nights)
3 bed/3 bath, sleeps 12
$1,660 ($332/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Jan 2–9, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$722 ($103/night)

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Sheraton Vistana Resort

Orlando, Florida

Jan 2–9, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,220 ($174/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Jan 2–9, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,425 ($204/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Jan 2–9, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$1,425 ($204/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Jan 2–16, 2026 (14 nights)
2 bed/2 bath, sleeps 8
$1,932 ($138/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Jan 3–7, 2026 (4 nights)
Studio/1 bath, sleeps 4
$1,414 ($353/night)

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Disney's Old Key West Resort

Lake Buena Vista, Florida

Jan 3–7, 2026 (4 nights)
Studio/1 bath, sleeps 4
$1,486 ($372/night)

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Disney's Beach Club Villas

Lake Buena Vista, Florida

Jan 3–6, 2026 (3 nights)
Studio/1 bath, sleeps 5
$1,452 ($484/night)

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Westgate Vacation Villas

Kissimmee, Florida

Jan 3–10, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$888 ($127/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Jan 3–6, 2026 (3 nights)
Studio/1 bath, sleeps 5
$1,654 ($552/night)