Book Luxury Winter Rentals in Florida

We selected the best homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights

Your Patch of Paradise

Your Patch of Paradise

  • 20 guests

  • 8 bedrooms

Manatee County, Florida

Generally reserved for golfing enthusiasts and beach lovers, this Florida home caters to both, but not without its own charm. A little paradise with a 'beach' for a backyard, volleyball and pickleball courts, a private swimming pool with fountains, ping pong and table football, and more, boredom is unlikely.

Take Me to the Ball Game

Take Me to the Ball Game

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

This Orlando vacation villa is a dream come true for families with kids who love Minions and Disney Princesses. The two themed bedrooms are decked out with bunk beds and decor from the beloved characters, sure to delight little ones.

The Sultan

The Sultan

  • 2 guests

  • 1 bedrooms

Parker Ridge, West Palm Beach

Utterly Instagrammable, this delightfully designed studio space offers you the perfect getaway in West Palm Beach. The layout is open plan, in a warehouse-style space that looks modern on the inside and Mediterranean on the outside.

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

This newly furnished and decorated single-family home is located in the Storey Lake community, close to Disney, Disney Springs, restaurants, and shopping centers. The cozy 7-bedroom home features 5 bathrooms, a game room with pool table and air hockey, a fully equipped kitchen, private screened pool and spa, and internet and cable.


We selected the top 3% holiday homes in Florida Vacation Rentals for Winter

Explore the 2 most perfect homes in our collection

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Most popular homes

A Drop of Sunlight

A Drop of Sunlight

  • 18 guests

  • 7 bedrooms

Nurmi Isles, Fort Lauderdale

The Lazy River

The Lazy River

  • 6 guests

  • 2 bedrooms

Osceola County, Florida

Beach Bliss Retreat

Beach Bliss Retreat

  • 10 guests

  • 4 bedrooms

Fort Walton Beach, Okaloosa County

Lakeside Getaway

Lakeside Getaway

  • 18 guests

  • 10 bedrooms

Barrier Island, Fort Lauderdale

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

Views In The Making

Views In The Making

  • 17 guests

  • 7 bedrooms

Cloud Lake, Palm Beach County

The Forte

The Forte

  • 12 guests

  • 6 bedrooms

Seven Isles, Fort Lauderdale

Pineapple Peach

Pineapple Peach

  • 18 guests

  • 8 bedrooms

Four Corners, Osceola County

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Frequently asked questions

Browse our remarkable collection of luxury Vacation Rentals for Winter in Florida. As only the top 3% of homes go on to become Plum Award winners, you can be certain that your chosen home will be ideal for you. Each home in our range must pass 3 rounds of testing, and comes fully furnished with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Make the most of the chilly season, and wrap up warm in a comfortable Winter Holiday Rental in Florida. Reach out to our caring team of experts, who love nothing more than helping you discover the perfect home for your trip.

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