Hillsborough County Luxury Houses

Award-winning homes from £98

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Home spotlights in Hillsborough County

The Sunshine Serenade

The Sunshine Serenade

  • 6 guests

  • 3 bedrooms

Four Corners, Osceola County

Located in a village resort just south of Orlando, this home with three double bedrooms and two bathrooms is a great space for larger families. The dining area lacks a bit of cosiness, but you’ll certainly find everything you need here for a comfortable stay.

Mighty Sweet

Mighty Sweet

  • 6 guests

  • 3 bedrooms

Riviera Beach, Florida

This home on Singer Island feels like a mid-century escape and is just footsteps from the beach. The nearest stretch of bone-white sand is a seven-minute walk away and you’re two blocks from Ocean Walk, where waterside walkways run past seafood restaurants, shops and cocktail bars.

Call of the Seabird

Call of the Seabird

  • 8 guests

  • 4 bedrooms

Anna Maria, Manatee County

Tucked among swaying palms on Florida’s stunning Anna Maria Island, this home is an ideal getaway for families or friends wanting to while away the hours in the sunshine. Inside, clean lines, neutral tones and lofty vaulted ceilings combine to create a space that’s inviting, bright and breezy.

Blue Water & Palm Trees

Blue Water & Palm Trees

  • 8 guests

  • 4 bedrooms

Sunshine Park, West Palm Beach

Not short on outdoor seating, this beautiful house embraces the tropical atmosphere of south Florida. The signature palm trees and meticulous landscape design surround the swimming pool creating an enchanting private oasis.


We selected the top 3% holiday homes in Hillsborough County Houses

Explore the 90 most perfect homes in our collection

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Most popular homes in Hillsborough County

Summer Lights

Summer Lights

  • 6 guests

  • 3 bedrooms

Harbour Inlet, Fort Lauderdale

The Forte

The Forte

  • 12 guests

  • 6 bedrooms

Seven Isles, Fort Lauderdale

Wake Up With the Sun

Wake Up With the Sun

  • 6 guests

  • 3 bedrooms

Atlantis, Florida

A Tide of Summer

A Tide of Summer

  • 16 guests

  • 9 bedrooms

Osceola County, Florida

Endless Ocean

Endless Ocean

  • 8 guests

  • 4 bedrooms

Birch Park Finger Streets, Fort Lauderdale

Naples Aglow

Naples Aglow

  • 8 guests

  • 4 bedrooms

Old Naples, Naples

A Little Sunset on the Waterfront

A Little Sunset on the Waterfront

  • 12 guests

  • 6 bedrooms

Harbor Beach, Fort Lauderdale

Coastal Daze

Coastal Daze

  • 10 guests

  • 5 bedrooms

Lauderdale-by-the-Sea, Broward County

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Frequently asked questions

All Plum Guide houses in Hillsborough County have been tested and approved by our team of independent home critics. These meticulous beings inspect everything –from the convenience of each house’s location right down to the art on the walls– so what you see really is what you get. Worried about thin curtains? Accessibility? Maybe wifi speed is your biggest concern? Rest assured, we obsessively check each house in Hillsborough County before approving it, so you can book with peace of mind.

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