Winter Rentals in Orlando

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Marriott's Harbour Lake

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,042 ($292/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,109 ($158/night)

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WorldMark Orlando Kingstown Reef

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,528 ($218/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,110 ($159/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 20–24, 2025 (4 nights)
1 bed/1 bath, sleeps 4
$445 ($111/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 20–27, 2025 (7 nights)
Studio/1 bath, sleeps 4
$722 ($103/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,330 ($190/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 20–26, 2025 (6 nights)
1 bed/1 bath, sleeps 4
$610 ($102/night)

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Marriott's Sabal Palms

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,660 ($237/night)

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Marriott's Sabal Palms

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,987 ($284/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,314 ($331/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 20–26, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$1,889 ($315/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,165 ($166/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,110 ($159/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,273 ($182/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,096 ($299/night)

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Orlando International Resort Club

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$555 ($79/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$855 ($122/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,110 ($159/night)

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The Fountains

Orlando, Florida

Dec 20, 2025 – Jan 1, 2026 (12 nights)
2 bed/2 bath, sleeps 8
$2,205 ($184/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$777 ($111/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$722 ($103/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$555 ($79/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 20–26, 2025 (6 nights)
1 bed/1 bath, sleeps 4
$832 ($139/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,960 ($280/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$844 ($121/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2.5 bath, sleeps 8
$1,110 ($159/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,840 ($549/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,110 ($159/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2.5 bath, sleeps 8
$1,110 ($159/night)

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Westgate Lakes Resort & Spa

Orlando, Florida

Dec 21–28, 2025 (7 nights)
3 bed/3 bath, sleeps 12
$1,110 ($159/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$777 ($111/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,932 ($276/night)

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Marriott's Imperial Palm Villas

Orlando, Florida

Dec 21–28, 2025 (7 nights)
3 bed/2 bath, sleeps 10
$2,205 ($315/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 21–27, 2025 (6 nights)
2 bed/2 bath, sleeps 6
$1,046 ($174/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 21–27, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$1,165 ($194/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,495 ($214/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 22–26, 2025 (4 nights)
Studio/1 bath, sleeps 4
$1,328 ($332/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 22–29, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 22–27, 2025 (5 nights)
Studio/1 bath, sleeps 4
$944 ($189/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 22–27, 2025 (5 nights)
Studio/1 bath, sleeps 4
$555 ($111/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 22–26, 2025 (4 nights)
2 bed/2 bath, sleeps 6
$944 ($236/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 22–27, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$832 ($166/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 22–27, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$832 ($166/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 22–27, 2025 (5 nights)
2 bed/2 bath, sleeps 6
$1,927 ($385/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 22–29, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,840 ($549/night)