Book Luxury Monthly Rentals in Hillsborough County

We selected the 866 homes worth renting in this location

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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 Monthly Rentals

Explore the 866 most perfect homes in our collection

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Most popular homes in Hillsborough County

Garden Of Tampa Delights

Garden Of Tampa Delights

  • 4 guests

  • 1 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

The Sea & The Sunset

The Sea & The Sunset

  • 16 guests

  • 8 bedrooms

Allen's Ridge, Palm Harbor

Raymond Retreat

Raymond Retreat

  • 6 guests

  • 3 bedrooms

Northwest Tampa, Tampa

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Frequently asked questions

Discover the ultimate collection of luxury Monthly Rentals in Hillsborough County, and say goodbye to all your travel troubles. Here at Plum Guide, it is our promise that each and every home in our range is in the top 3% of homes in its location, so there is no doubting the consistent quality we are able to offer. Secure your extended or short stay today and enjoy the trip of a lifetime in your fully furnished home, with every property on our site including all linens, essential bathroom toiletries, and a perfectly-equipped kitchen. Our meticulous home critics test everything from Wifi speed to a home's design, so you really can trust our judgement. Rent your perfect Hillsborough County Monthly Apartment today with the help of our team of experts, on standby 24/7 to assist you with absolutely anything.

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