Family-friendly vacation rentals in Hillsborough County

Ultra Modern Pool Home w/ rooftop private HOT TUB

Your vacation at Cigar City Mansion will put you in the heart of one of the most electric areas of Tampa for those who like to have fun but also relax. This home is walking distance from the best restaurants in Tampa. When it’s time to kick back, Cigar City Mansion provides the amenities to do so, including your own private hottub & firepit on the open-air rooftop of your home, you’ll feel like you’re in natute in the middle of the city, huge swimming pool & BBQ grill just outside your door

Adorable Suite: 15min to beach, 10min downtown

Entire apartment with a complete kitchen, full bath, A/C, WiFi (300mbps), you have a private entrance and all the comforts of home. Comfortable queen size bed. You are located 15 minutes from St Pete Beach and 10 minutes to downtown St Pete. You have off street parking. Very safe and quiet location. You have an easy check in via lock box after 3pm, and check out is simple, leave the key then lock the door behind you. We have plenty of secret spots to recommend. Very experienced Super Hosts.

Luxury Townhome - Tampa/Hyde Park/Amalie/Bucs

Location & Comfort! Expertly furnished & decorated 3/3.5 townhouse for up to 7 guests w/ all the modern conveniences you need. Park in your 2-car garage but walk to the very best of what S. Tampa & Downtown have to offer. Urban location just 1 block from the splendor of Bayshore Blvd. Walking distance to Hyde Park Village, the Riverwalk, University of Tampa, Amalie Arena, Convention Center, Tampa General Hospital, Davis Islands & Gasparilla parades. Just a 5-10 min Uber ride to Ybor City.

Tampa Heights Bungalow (Close to UT, Downtown)

Bungalow style home located in historic Tampa Heights. Really convenient to everything. Just minutes from Downtown Tampa, University of Tampa, Raymond James Stadium or Busch Gardens. All the furnishings are set up for your enjoyment and comfort. You will have the entire house which is located in a great area just north of Armature Works and the Riverwalk. Whether you are visiting Tampa for business or pleasure, you will be much more comfortable here than staying in a hotel.

Seminole Heights Riverside Paradise w/Pool

Whether you're traveling for business, seeking a FL adventure or a short getaway staycation, the stunning waterfront views, pool & incredible amenities with convenient proximity to downtown Tampa, airport & area attractions, the guesthouse at Isla de Dij is the perfect accommodation. You'll fall in love with the massive live oaks that line the brick paved streets, the glassy waters of the Hillsborough River and the brilliant sunsets that paint the evening sky.

Tropical Paradise

Please visit our website Grovekeeper collective for a video of the property Private vacation rental I know if you are coming to Delightful Dunedin you know how amazing this waterfront community is, from award winning restaurants , micro breweries, one of the #1 beaches in America, 40 miles of bike trails, waterfront parks. Just bring food and clothes, we have the rest covered! This rental is for a maximum of 5 guest all our units are non-smoking and vaping

Tranquil poolside guesthouse on the river

The apartment is on the Hillsborough River surrounded by nature but only 3 minutes away from the great restaurants, bars and breweries of Seminole Heights. It is walking distance to Lowry Park Zoo and park. Spot the beautiful Florida wildlife up close from the river dock. Soak in the outdoor pool surrounded by mature live oaks or take a canoe out on the river. Top beaches are 35 minutes by car. Great for a couple or a small family.

Pool + Park + Private = Perfect Place

Our 1300 sf abode is close to everything that Tampa has to offer. Restaurants, breweries, downtown, the airport, sports/concert arenas, the zoo, the aquarium, Ybor & the Riverwalk. Don't feel like eating out? Fire up the grill or utilize the full kitchen. Ready to relax? Jump in the salt water pool & get some sun. As the day ends, take a sunset walk along the Hillsborough river, across the street at Rivercrest Park.

'Big' Tiny House in Historic Ybor City

We designed this little house with a little more room than your typical tiny house, and it's a bit more modern than the 'shotgun shacks' in the neighborhood. The house is centrally located in historic Ybor City, Tampa -- three blocks from the main drag of 7th avenue, and less than five minutes from the cruise terminal, Amalie Arena, Tampa convention center, and downtown. Designed and built by us in 2018.