Winter Rentals in Florida

Verified & Protected Voted Top Pick 2025

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,513 ($502/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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$955 ($136/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 20–24, 2025 (4 nights)
3 bed/3 bath, sleeps 10
$2,586 ($647/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$6,521 ($932/night)

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The Banyan Resort

Key West, Florida

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,769 ($253/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 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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Marriott's Grande Vista

Orlando, Florida

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

Verified & Protected Voted Top Pick 2025

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,859 ($408/night)

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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
$2,096 ($299/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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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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Westgate Towers

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,320 ($189/night)

Verified & Protected Voted Top Pick 2025

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–27, 2025 (7 nights)
Studio/1 bath, sleeps 4
$2,423 ($346/night)

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Soundside Holiday Beach Resort

Pensacola Beach, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,165 ($166/night)

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Holiday Inn Club Vacations Marco Island - Sunset Cove Resort

Marco Island, Florida

Dec 20–27, 2025 (7 nights)
3 bed/2 bath, sleeps 8
$2,640 ($377/night)

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Silver Lake Resort

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,358 ($194/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,231 ($176/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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Sheraton Vistana Villages

Orlando, Florida

Dec 21–27, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$699 ($117/night)

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Palm Beach Shores Resort and Vacation Villas

Palm Beach Shores, Florida

Dec 21–28, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,054 ($151/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$999 ($143/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$6,238 ($891/night)

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Vacation Villas at Fantasy World

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,330 ($190/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 21–26, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$3,731 ($746/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,532 ($362/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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Hyatt Beach House Resort

Key West, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,696 ($385/night)

Verified & Protected Voted Top Pick 2025

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 21–28, 2025 (7 nights)
Studio/1 bath, sleeps 4
$1,877 ($268/night)

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Emerald Grande at HarborWalk Village

Destin, Florida

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

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Hyatt Sunset Harbor Resort

Key West, Florida

Dec 21–28, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,550 ($221/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–27, 2025 (6 nights)
1 bed/1 bath, sleeps 4
$942 ($157/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 Villages

Orlando, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$777 ($111/night)

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Hyatt Beach House Resort

Key West, Florida

Dec 21–25, 2025 (4 nights)
2 bed/2 bath, sleeps 6
$832 ($208/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)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

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Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 21–28, 2025 (7 nights)
4 bed/4 bath, sleeps 12
$4,385 ($626/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,583 ($226/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,110 ($159/night)

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Club Wyndham Sea Gardens

Pompano Beach, Florida

Dec 21–28, 2025 (7 nights)
Studio/1 bath, sleeps 2
$998 ($143/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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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 21–26, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$855 ($171/night)

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Marriott's Oceana Palms

Riviera Beach, Florida

Dec 21–27, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$3,851 ($642/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)

Verified & Protected

Westgate Town Center

Kissimmee, Florida

Dec 21–28, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,542 ($220/night)