Book Luxury Holiday Rentals in Hillsborough County

Award-winning homes from £98

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Hillsborough County

Naples Aglow

Naples Aglow

  • 8 guests

  • 4 bedrooms

Old Naples, Naples

You’ll find this modern, adult-only home in Old Naples, a short walk from Fifth Avenue with its plethora of delicious eateries and trendy shops. Comfortable for eight, each bedroom boasts an ensuite and with two separate living areas, there’s plenty of room for guests to spread out here.

Dream of the Open Sea

Dream of the Open Sea

  • 12 guests

  • 6 bedrooms

Harbour Inlet, Fort Lauderdale

Floor-to-ceiling windows mean that you don’t even have to try to tear your eyes away from the water view here. This home sits on the edge of Harbor Inlet, looking out over the Port Everglades waterway.

Worth the While

Worth the While

  • 16 guests

  • 5 bedrooms

Hypoluxo, Palm Beach County

If you're in possession of a boat, this Floridian villa has a rather unique feature that might just appeal to you. Along the private deck facing Lake Worth Lagoon, there's a lift that can move vessels weighing up to 13,000 pounds so you can explore the body of water as well as the Atlantic Ocean beyond that.

Tampa Tranquil

Tampa Tranquil

  • 3 guests

  • 1 bedrooms

Northwest Tampa, Tampa

Entwined in the authentic threads of Northwest Tampa, this retreat offers a mesmerizing blend of urban vitality and familial tranquility. A stone's toss from Raymond James Stadium, downtown sisblings Ybor City and Hyde Park Village, exploration comes abundantly.


We selected the top 3% holiday homes in Hillsborough County Holiday Rentals

Explore the 866 most perfect homes in our collection

View on map

Most popular homes in Hillsborough County

The Sea & The Sunset

The Sea & The Sunset

  • 16 guests

  • 8 bedrooms

Allen's Ridge, Palm Harbor

Sunlit Hideaway

Sunlit Hideaway

  • 4 guests

  • 1 bedrooms

Palm Beach, Palm Beach County

A Florida Place to call Home

A Florida Place to call Home

  • 10 guests

  • 4 bedrooms

Lake County, Florida

Evergreen Tree

Evergreen Tree

  • 16 guests

  • 6 bedrooms

Brevard County, Florida

Rockpool

Rockpool

  • 8 guests

  • 4 bedrooms

Victoria Park, Fort Lauderdale

A Miami To Go

A Miami To Go

  • 2 guests

  • 2 bedrooms

Central Beach, Fort Lauderdale

Garden Of Tampa Delights

Garden Of Tampa Delights

  • 4 guests

  • 1 bedrooms

Northwest Tampa, Tampa

Sea View Sanctuary

Sea View Sanctuary

  • 20 guests

  • 7 bedrooms

Osceola County, Florida

View all

Check upcoming rates & availability for Hillsborough County Holiday Rentals


Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Hillsborough County. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Hillsborough County has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

Search Our Collection