Winter Rentals in Florida

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Sheraton Vistana Resort

Orlando, Florida

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,042 ($292/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$999 ($143/night)

Verified & Protected Voted Top Pick 2025

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 19–27, 2025 (8 nights)
1 bed/1 bath, sleeps 4
$2,205 ($276/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$5,475 ($782/night)

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Hurricane House

Sanibel Island, Florida

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,204 ($315/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 19–24, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$555 ($111/night)

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Westgate Palace

Orlando, Florida

Dec 19–26, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,660 ($237/night)

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Enchanted Isle Resort

Hollywood, Florida

Dec 20, 2025 – Jan 3, 2026 (14 nights)
2 bed/1 bath, sleeps 6
$4,385 ($313/night)

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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,286 ($184/night)

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Holiday Inn Club Vacations at Orange Lake Resort - North Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,769 ($253/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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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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Coral Reef Beach Resort

St. Pete Beach, Florida

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,660 ($237/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 20–26, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$1,264 ($211/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/night)

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Westgate Vacation Villas

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,166 ($167/night)

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Palm Beach Shores Resort and Vacation Villas

Palm Beach Shores, Florida

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$2,014 ($288/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,374 ($196/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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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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Hyatt Windward Pointe Resort

Key West, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,095 ($299/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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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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,286 ($184/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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Club Wyndham Cypress Palms

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,286 ($184/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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Marriott's Villas at Doral

Miami, Florida

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

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Hilton Vacation Club Aqua Sol Orlando West

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
3 bed/3 bath, sleeps 10
$1,932 ($276/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
$7,000 ($1,000/night)

Verified & Protected Voted Top Pick 2025

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 20–27, 2025 (7 nights)
1 bed/1 bath, sleeps 4
$1,987 ($284/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/3 bath, sleeps 8
$2,859 ($408/night)

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Camaron Cove Resort

Indian Rocks Beach, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,205 ($315/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)

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
$4,494 ($642/night)

The Galleon Resort

Key West, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$4,112 ($588/night)

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Hyatt Siesta Key Beach - A Hyatt Residence Club

Siesta Key, Florida

Dec 20–27, 2025 (7 nights)
3 bed/3 bath, sleeps 8
$7,655 ($1,094/night)

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Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,642 ($235/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,440 ($206/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
$4,494 ($642/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
$1,110 ($159/night)

CHOOSE YOUR OWN DATES

Club Wyndham Bonnet Creek Resort

Lake Buena Vista, Florida

Dec 20–25, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$550 ($110/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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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

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

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Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,878 ($268/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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Westgate Lakes Resort & Spa

Orlando, Florida

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