Winter Rentals in Florida

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The Fountains

Orlando, Florida

Dec 23–29, 2025 (6 nights)
2 bed/2 bath, sleeps 8
$832 ($139/night)

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Disney's Polynesian Villas & Bungalows

Lake Buena Vista, Florida

Dec 23, 2025 – Jan 1, 2026 (9 nights)
Studio/1 bath, sleeps 5
$8,200 ($911/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 23–25, 2025 (2 nights)
1 bed/1 bath, sleeps 4
$335 ($168/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 23–28, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$999 ($200/night)

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Hilton Grand Vacations at Tuscany Village

Orlando, Florida

Dec 23–28, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$1,104 ($221/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 23–26, 2025 (3 nights)
2 bed/2 bath, sleeps 8
$610 ($204/night)

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Holiday Inn Club Vacations at Orange Lake Resort - East Village

Kissimmee, Florida

Dec 23–28, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$1,220 ($244/night)

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Hilton Grand Vacations at SeaWorld

Orlando, Florida

Dec 23–29, 2025 (6 nights)
2 bed/2 bath, sleeps 6
$1,550 ($258/night)

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Disney's Saratoga Springs Resort & Spa

Lake Buena Vista, Florida

Dec 23–27, 2025 (4 nights)
2 bed/2 bath, sleeps 8
$4,930 ($1,232/night)

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Holiday Inn Club Vacations at Orange Lake Resort - River Island

Kissimmee, Florida

Dec 23–27, 2025 (4 nights)
2 bed/2 bath, sleeps 8
$555 ($139/night)

Marriott's Grande Vista

Orlando, Florida

Dec 23–26, 2025 (3 nights)
2 bed/2 bath, sleeps 8
$998 ($333/night)

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Hyatt Windward Pointe Resort

Key West, Florida

Dec 23–27, 2025 (4 nights)
2 bed/2 bath, sleeps 6
$1,714 ($429/night)

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Hilton Grand Vacations at Tuscany Village

Orlando, Florida

Dec 23–26, 2025 (3 nights)
2 bed/2 bath, sleeps 6
$502 ($167/night)

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Marriott's Legends Edge at Bay Point

Panama City Beach, Florida

Dec 23–27, 2025 (4 nights)
2 bed/2 bath, sleeps 8
$831 ($208/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 23–28, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$1,495 ($299/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 24–26, 2025 (2 nights)
1 bed/1 bath, sleeps 4
$220 ($110/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 24–26, 2025 (2 nights)
1 bed/1 bath, sleeps 4
$254 ($127/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 24, 2025 – Jan 2, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$11,470 ($1,274/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 24–26, 2025 (2 nights)
3 bed/3 bath, sleeps 10
$2,150 ($1,075/night)

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Disney's BoardWalk Villas

Lake Buena Vista, Florida

Dec 24–25, 2025 (1 night)
Studio/1 bath, sleeps 5
$635 ($635/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 24–27, 2025 (3 nights)
1 bed/1 bath, sleeps 4
$999 ($333/night)

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Parc Soleil by Hilton Grand Vacations

Orlando, Florida

Dec 24, 2025 – Jan 2, 2026 (9 nights)
1 bed/1 bath, sleeps 4
$1,495 ($166/night)

Verified & Protected Voted Top Pick 2025

Marriott's Ocean Pointe

Palm Beach Shores, Florida

Dec 24, 2025 – Jan 1, 2026 (8 nights)
Studio/1 bath, sleeps 4
$2,205 ($276/night)

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Disney's Animal Kingdom Villas - Jambo House

Lake Buena Vista, Florida

Dec 24–26, 2025 (2 nights)
Studio/1 bath, sleeps 4
$1,277 ($639/night)

Verified & Protected Voted Top Pick 2025

Marriott's Crystal Shores

Marco Island, Florida

Dec 25, 2025 – Jan 3, 2026 (9 nights)
2 bed/2 bath, sleeps 8
$11,470 ($1,274/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 25, 2025 – Jan 1, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,462 ($352/night)

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Wyndham Beach Street Cottages

Destin, Florida

Dec 25, 2025 – Jan 2, 2026 (8 nights)
1 bed/1 bath, sleeps 6
$1,660 ($208/night)

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Marriott's Harbour Lake

Orlando, Florida

Dec 25, 2025 – Jan 1, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$2,423 ($346/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 25–30, 2025 (5 nights)
2 bed/2 bath, sleeps 8
$1,495 ($299/night)

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Marriott's Sabal Palms

Orlando, Florida

Dec 25, 2025 – Jan 1, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,022 ($432/night)

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Marriott's Lakeshore Reserve

Orlando, Florida

Dec 25, 2025 – Jan 1, 2026 (7 nights)
3 bed/3 bath, sleeps 12
$4,603 ($658/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 25, 2025 – Jan 1, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,165 ($166/night)

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Holiday Inn Club Vacations at Orange Lake Resort - West Village

Kissimmee, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,660 ($237/night)

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Westgate Town Center

Kissimmee, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,922 ($275/night)

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Hilton Grand Vacations at McAlpin-Ocean Plaza

Miami Beach, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,840 ($549/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,022 ($432/night)

Verified & Protected Voted Top Pick 2025

Marriott's BeachPlace Towers

Fort Lauderdale, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$3,077 ($440/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)

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Westgate Blue Tree Resort

Orlando, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
1 bed/1 bath, sleeps 4
$1,080 ($154/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,022 ($432/night)

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Westgate Town Center

Kissimmee, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,878 ($268/night)

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Westgate Town Center

Kissimmee, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,905 ($272/night)

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Sheraton Vistana Resort

Orlando, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$1,439 ($206/night)

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Marriott's Grande Vista

Orlando, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$3,022 ($432/night)

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Tortuga Beach Club

Sanibel Island, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 6
$3,295 ($471/night)

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Club Wyndham Panama City Beach

Panama City Beach, Florida

Dec 26–31, 2025 (5 nights)
1 bed/1 bath, sleeps 4
$555 ($111/night)

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Sheraton Vistana Villages

Orlando, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,330 ($190/night)

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Marriott's Cypress Harbour Villas

Orlando, Florida

Dec 26, 2025 – Jan 2, 2026 (7 nights)
2 bed/2 bath, sleeps 8
$1,550 ($221/night)