Book Luxury Summer Rentals in Hillsborough County

We selected the 866 homes worth renting in this location

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Age 1 to 12

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Home spotlights in Hillsborough County

Summer's Insomniac Dream

Summer's Insomniac Dream

  • 10 guests

  • 4 bedrooms

Osceola County, Florida

This stunning brand new vacation rental is a 4 bedroom, 3 bathroom property located in Storey Lake Resort. With two king bedrooms, one queen bedroom, and a bedroom with 2 twin beds plus a full sofa bed, this property can comfortably accommodate up to 10 guests.

A Drop of Sunlight

A Drop of Sunlight

  • 18 guests

  • 7 bedrooms

Nurmi Isles, Fort Lauderdale

Discover a different side of Florida when you visit this bright and modern villa in the Nurmi Isles of Fort Lauderdale. Not known as the Venice of America for nothing, a network of canals surrounds the neighbourhood, giving way to a beautiful view from the firepit and the private swimming pool.

Orchid White

Orchid White

  • 16 guests

  • 7 bedrooms

Parker Ridge, West Palm Beach

It’s hard to know where to begin when describing this 1920s estate, there are so many incredible details. The main house is a grand, Spanish-style villa housing four bedrooms.

A Disney Mania

A Disney Mania

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

This 6-bed/5-bath villa in Orlando is perfect for a family vacation. The villa features two epic-themed bedrooms, including a Minions and Ironman bedroom, that will keep the kids entertained all night long.


We selected the top 3% holiday homes in Hillsborough County Vacation Rentals for Summer

Explore the 866 most perfect homes in our collection

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Most popular homes in Hillsborough County

Lakeside Getaway

Lakeside Getaway

  • 18 guests

  • 10 bedrooms

Barrier Island, Fort Lauderdale

Views In The Making

Views In The Making

  • 17 guests

  • 7 bedrooms

Cloud Lake, Palm Beach County

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

Sunshine Magic

Sunshine Magic

  • 16 guests

  • 8 bedrooms

Coral Ridge, Fort Lauderdale

Sunshine Sweets

Sunshine Sweets

  • 10 guests

  • 3 bedrooms

Coral Ridge Isles, Fort Lauderdale

The Magic Kingdom

The Magic Kingdom

  • 8 guests

  • 4 bedrooms

Four Corners, Osceola County

Sugar Sky

Sugar Sky

  • 24 guests

  • 10 bedrooms

Polk County, Florida

Endless Ocean

Endless Ocean

  • 8 guests

  • 4 bedrooms

Birch Park Finger Streets, Fort Lauderdale

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Check upcoming rates & availability for Hillsborough County Vacation Rentals for Summer


Frequently asked questions

Explore our remarkable range of luxury Summer Rentals in Hillsborough County. There's no time for average stays, so treat yourself to a stay in one of the most impressive rentals around. Each and every home in our selection is put through numerous rounds of thorough testing, with everything from shower pressure to a home's design being closely checked for quality. Only the finest 3% of homes are awarded the prestigious Plum Award, so you can book with total confidence. Rentals in our range come fully furnished, with a well-equipped kitchen, essential bathroom toiletries, and all linen included to make you feel right at home. Book a memorable trip to an unforgettable Vacation Rental for Summer in Hillsborough County today, and make the most of the year's warmest season. If you require any assistance, call on the help of our experts - they're on-hand to help you discover the perfect home.

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