Hillsborough County Holiday Homes with Staff

We selected the 866 homes worth renting in this location

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

The Magic Kingdom

The Magic Kingdom

  • 8 guests

  • 4 bedrooms

Four Corners, Osceola County

This modern single-story villa is the perfect place to relax and enjoy your holiday in Orlando. With a row of comfy bedrooms that can sleep up to eight guests, you'll have plenty of space to spread out and relax.

Take Me to the Ball Game

Take Me to the Ball Game

  • 16 guests

  • 6 bedrooms

Four Corners, Osceola County

This Orlando vacation villa is a dream come true for families with kids who love Minions and Disney Princesses. The two themed bedrooms are decked out with bunk beds and decor from the beloved characters, sure to delight little ones.

Vintage Oasis

Vintage Oasis

  • 6 guests

  • 3 bedrooms

Sunny Point, Melbourne

This fabulous historic home nestled among huge oak trees has been completely renovated to offer vintage flair AND modern comforts. This lovingly restored 1908 home is just 2 blocks from the Eau Gallie Arts District (EGAD) brimming with local creative ventures, many galleries, museums, murals, boutiques, bars and restaurants.

The Great Blue Hole

The Great Blue Hole

  • 18 guests

  • 7 bedrooms

Four Corners, Osceola County

This is the perfect vacation home for families looking for a fun-filled getaway. Kids will love the superhero and Fashionista-themed bedrooms, complete with over-the-top bunk beds and decor.


We selected the top 3% holiday homes in Hillsborough County Holiday Homes with Staff

Explore the 866 most perfect homes in our collection

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Most popular homes in Hillsborough County

Tampa Treasure

Tampa Treasure

  • 4 guests

  • 2 bedrooms

Northwest Tampa, Tampa

The Forte

The Forte

  • 12 guests

  • 6 bedrooms

Seven Isles, Fort Lauderdale

Black & White Paradise

Black & White Paradise

  • 4 guests

  • 2 bedrooms

Osceola County, Florida

Naples Aglow

Naples Aglow

  • 8 guests

  • 4 bedrooms

Old Naples, Naples

Dream of the Open Sea

Dream of the Open Sea

  • 12 guests

  • 6 bedrooms

Harbour Inlet, Fort Lauderdale

Worth the While

Worth the While

  • 16 guests

  • 5 bedrooms

Hypoluxo, Palm Beach County

Tampa Tranquil

Tampa Tranquil

  • 3 guests

  • 1 bedrooms

Northwest Tampa, Tampa

The Sea & The Sunset

The Sea & The Sunset

  • 16 guests

  • 8 bedrooms

Allen's Ridge, Palm Harbor

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Check upcoming rates & availability for Hillsborough County Holiday Homes with Staff


Frequently asked questions

Are you hoping for a stay in one of the best holiday homes with staff in Hillsborough County? If so, you've definitely come to the right place. Reach out to our expert team who will happily arrange for staff to be present at your home in Hillsborough County as an addition to your booking. Our Plum Guide homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short extended stay. Should you need anything, our friendly team is on hand 24/7, so just ask.

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