Family-friendly holiday rentals in Hillsborough County

Adorable South Tampa Two-Story Guest House

My place is close to restaurants and dining, art & culture, Tampa International Airport (4 miles), Raymond James Stadium & Legends Field(2.4 miles), downtown (3 miles), Tampa Amalie Arena (3.3 miles), MIDFLORIDA Amphitheatre (10.8 miles), Florida State Fairgrounds (11.9 miles). Many beaches to choose from within approximately 30 minutes. You’ll love my place because of the location and the coziness. My place is good for couples, solo adventurers, business travelers, and families (with kids).

Charming private guest house.

Our charming one bedroom guest cottage on Davis Islands sleeps 2 (queen-sized bed). Bathroom with large shower. Clean and cozy room has cable tv, wi-fi, mini fridge, microwave, Keurig coffee maker. Gorgeous neighborhood, walking distance to downtown DI restaurants, coffee shops, rentable bikes, Amalie Arena, the Riverwalk, Hyde Park, downtown Tampa, the Convention Center, Channelside & TGH. 2 miles from cruise port. 15 min. drive to Bush Gardens. Enjoy the sunset at the end of the island.

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

***Beautiful Hyde Park Apartment***

This location is hard to beat!! This tranquil apartment is one of four, located in a historic building from 1910 in Hyde Park! It is conveniently located within walking distance to Downtown Tampa, shopping and restaurants, yet is located on a quiet peaceful street. In the midst of Hyde Park, close to absolutely everything... The Tampa Convention Center, The Riverwalk, Hyde Park Villages, University of Tampa, Downtown, Davis Island, Tampa General Hospital, Amalie Arena and Bayshore Blvd.

Smack in the middle of everything Tampa

Full renovation of this 1927 cottage has transformed this home into a gorgeous , highly styled retreat with all the modern conveniences of a spectacular home. Central AC and heat, fans in every room, screened in porches, laundry room and dryer with all detergents,etc. open floor plan, as well as a private and quaint backyard oasis with fire pit, umbrella and hammock. Best location with outstanding restaurants and bars in walking distance, as well as interstate 275 only 5 minutes away.

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.

Tropical 1920s Bungalow with Saltwater Pool

Step into the charm of Old Florida with this 1920s South Tampa bungalow. Nestled beneath grand oak trees on a quiet corner lot in the eclectic Ballast Point neighborhood, this cozy cottage blends vintage charm with modern comfort. This inviting retreat features a tropical backyard oasis, complete with saltwater pool, swaying palms, and cozy outdoor lounging areas - perfect for morning coffee, afternoon sun, or evening swims.

Backyard Bungalow in Old Seminole Heights

Newly renovated "studio" In-law suite built in 1947. The suite is flooded with natural light and exposure from all angles. Access to backyard. Full kitchen w/ stainless steel appliances, A/C and stackable washer/dryer (detergent is not provided) Complimentary: coffee, tea, basic condiments and spices, shampoo/conditioner, body wash, three complimentary bottles of water (for arrival only), coffee maker and toaster in suite.

'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.