Rent Luxury Holiday Cottages in Hillsborough County

We selected the 0 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights

Singing Sweet Carolina

Singing Sweet Carolina

  • 12 guests

  • 6 bedrooms

Hilton Head Island, Beaufort County

A sweet summer’s day comes easy in this elegant, Georgian-style home. After a rejuvenating sleep in one of the lavish bedrooms, all you’ll want is to get out into the sun.

Orange & Sand

Orange & Sand

  • 6 guests

  • 3 bedrooms

Harbor Beach, Fort Lauderdale

A private dock on the canals of Fort Lauderdale and your own swimming pool by the waterside – this cosy cottage is ideal for boaties and waterbabies. If you’re not exploring the area by kayak, boat or paddleboard, you can rent bikes and go by land.

Wicker

Wicker

  • 12 guests

  • 4 bedrooms

Hilton Head Island, Beaufort County

Surrounded by lagoons on all sides, this low-country home is tucked into the flora and fauna of Hilton Head Island. The gracious nature of the home makes it ideal for both a short summer weekend and long stay alike.

Wake Up With the Sun

Wake Up With the Sun

  • 6 guests

  • 3 bedrooms

Atlantis, Florida

Spend just a few moments admiring the views of the small lake and verdant fairways, and you'll understand why this contemporary bungalow is a relaxing retreat. Situated in the gated Atlantis community, this home oozes sparkle.


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

Explore the 0 most perfect homes in our collection

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Most popular homes

Love Is A Dream

Love Is A Dream

  • 12 guests

  • 3 bedrooms

Richmond West, Miami-Dade County

Sea Grape

Sea Grape

  • 4 guests

  • 2 bedrooms

Walker Grant, New Smyrna Beach

Key to the Garden

Key to the Garden

  • 10 guests

  • 4 bedrooms

Miami-Dade County, Florida

Sunshine Sleeper

Sunshine Sleeper

  • 6 guests

  • 2 bedrooms

Cutler Bay, Miami-Dade County

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Frequently asked questions

Discover our curated collection of luxury holiday Cottages in Hillsborough County, Florida, United States. We painstakingly review all homes available in a destination and accept only the top 3% to ensure quality our guests can trust. Each of the Hillsborough County Cottages in our collection comes fully furnished with essential bathroom toiletries, expertly-equipped kitchens and all linens included. Book your dream stay today and should you need some help, our friendly team of experts are on hand to help plan your perfect Cottage break.

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