Winter Rentals in Florida

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Vacation Villas at Fantasy World

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,932 ($276/night)

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Marriott's Royal Palms

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,219 ($174/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$832 ($119/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 20–27, 2025 (7 nights)
3 bed/3 bath, sleeps 12
$1,550 ($221/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
$4,385 ($626/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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Marriott's Royal Palms

Orlando, Florida

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

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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
$1,220 ($174/night)

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The Resort on Cocoa Beach

Cocoa Beach, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,932 ($276/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)

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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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Marriott's Grande Vista

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$3,894 ($556/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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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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Hilton Vacation Club Aqua Sol Orlando West

Kissimmee, Florida

Dec 20–24, 2025 (4 nights)
2 bed/2 bath, sleeps 6
$555 ($139/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
$3,832 ($547/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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Holiday Inn Club Vacations Cape Canaveral Beach Resort

Cape Canaveral, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,302 ($186/night)

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Hyatt Vacation Club At Coconut Cove

Bonita Springs, Florida

Dec 20–24, 2025 (4 nights)
Studio/1 bath, sleeps 4
$555 ($139/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
$998 ($143/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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Westgate Town Center

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$2,586 ($370/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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Marriott's Sabal Palms

Orlando, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,385 ($198/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
$1,550 ($221/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
$1,660 ($237/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)

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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Club Wyndham Cypress Palms

Kissimmee, Florida

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

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,385 ($198/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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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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Palm Beach Shores Resort and Vacation Villas

Palm Beach Shores, Florida

Dec 20, 2025 – Jan 3, 2026 (14 nights)
2 bed/2 bath, sleeps 6
$4,603 ($329/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
$3,513 ($502/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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The Resort on Cocoa Beach

Cocoa Beach, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$1,330 ($190/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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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,088 ($155/night)

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Vanderbilt Beach and Harbour Club

Naples, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 6
$2,968 ($424/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
$1,660 ($237/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 Grande Vista

Orlando, Florida

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

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 20–27, 2025 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/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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Sheraton Vistana Resort

Orlando, Florida

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