Family-friendly holiday rentals in Hillsborough County

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

Multi-Award Winning & Top 5% Rated on Airbnb 2025

“The Pickett Fence” is a recognized Historic Farmhouse Inn that was built in 1920’s. ~SORRY, NO CHILDREN!~ Included: *Free WiFi *FireStick, Netflix, Hulu, Peacock, MAX *Paramount+ *3 large bedrooms W/TV & Fire-stick *2.5 baths *Chef Gourmet Kitchen & amenities *Private Hot-tub for 6 with Bluetooth Only minutes away to- 😍 Ybor Downtown Amalie Arena Convention C. Riverwalk Raymond Stadium Adventure Is. Busch Gardens USF T.I.A International Mall Westshore Mall 20-25 Minutes to- Beaches

***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.

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.

The Lemon Studio Near Downtown Tampa

Settle in at the newly built lemon studio, a modern but cozy centrally located studio just outside of downtown Tampa. North Hyde Park is just a few minutes from the airport and has easy access to the interstate. The studio has many walkable restaurants and parks. Enjoy nearby the University of Tampa, breweries, Sparkmans Warf, River Walk, Armature Works, shopping in Hyde Park Village and many local attractions... Parking available/Self-check in, come and goes as you please.

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.

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.