Book Luxury Vacation Rentals in Hillsborough County

Award-winning homes from £98

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Home spotlights in Hillsborough County

Palm Mansion

Palm Mansion

  • 16 guests

  • 8 bedrooms

Allen's Ridge, Palm Harbor

This Palm Harbor mansion is perfect for making memories. It’s just a ten-minute drive from the sandy shores of Honeymoon Island, but you may never want to leave the house.

Water Worlds

Water Worlds

  • 10 guests

  • 4 bedrooms

Pinellas County, Florida

For a restful and unforgettable stay in Florida, this lovely home situated in Clearwater is a great choice for a family or a group of friends. Just a short distance from the many beaches and outdoor attractions that the area has in store, this cosy gem offers plenty of charm and home comforts too.

Tampa Treasure

Tampa Treasure

  • 4 guests

  • 2 bedrooms

Northwest Tampa, Tampa

Discover the treasure of Tampa at this charming retreat, nestled amidst high-end eateries, bars and irresistible shopping destinations. It's located just a stroll away from an array of urban amenities including the illustrious Raymond James Stadium, downtown, Ybor City and Hyde Park Village.

Garden Of Tampa Delights

Garden Of Tampa Delights

  • 4 guests

  • 1 bedrooms

Northwest Tampa, Tampa

Nestled in Tampa's bustling heart, this home offers an eclectic blend of urban vibrancy and homely comfort. Just a stone's throw away from Raymond James Stadium and downtown, the location opens a world of high-end eateries and shopping opportunities.


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

Explore the 970 most perfect homes in our collection

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Most popular homes in Hillsborough County

Raymond Retreat

Raymond Retreat

  • 6 guests

  • 3 bedrooms

Northwest Tampa, Tampa

Tampa Tranquil

Tampa Tranquil

  • 3 guests

  • 1 bedrooms

Northwest Tampa, Tampa

Evergreen Tree

Evergreen Tree

  • 16 guests

  • 6 bedrooms

Brevard County, Florida

A Disney Mania

A Disney Mania

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Summer Nights in Summery Places

Summer Nights in Summery Places

  • 12 guests

  • 5 bedrooms

Brevard County, Florida

Take Me to the Ball Game

Take Me to the Ball Game

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

Call of the Seabird

Call of the Seabird

  • 8 guests

  • 4 bedrooms

Anna Maria, Manatee County

The Sultan

The Sultan

  • 2 guests

  • 1 bedrooms

Parker Ridge, West Palm Beach

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Frequently asked questions

Take a look at our collection of luxury Vacation Rentals in Hillsborough County. All of the homes you'll find on Plum Guide come fully furnished with all linen, the best-equipped kitchens, and essential bathroom toiletries included. Each home is systematically reviewed before becoming part of our collection, so you can book your stay with total confidence. And if you require any assistance in finding the perfect Hillsborough County Vacation Rentals for you, get in touch with our team of friendly experts, on hand to help with whatever you need.

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