Family-friendly holiday rentals in Hillsborough County

A vibrant outdoor oasis features a cozy plunge pool surrounded by sun loungers. A shaded seating area includes a table with four chairs. The space is enhanced by decorative elements, including a pergola with hanging egg chairs, all set against a lush green lawn.

4.97 out of 5 average rating, 112 reviews

Cozy Family Retreat, Tampa: Private Pool Oasis

Welcome to Sunshine on the Bay, a charming 2-bed/1-bath villa that blends comfort and style in a quiet area. Located just 3 mins from Citrus Park Mall and 13 mins from airport you'll have easy access to shopping, dining, and top Tampa attractions. Step outside into your own private backyard oasis, complete with a refreshing plunge pool & grill – the perfect spot to unwind after a long day. Enjoy all the essentials, fully equipped kitchen, as well as a 240V outlet for your EV charger. Book today!

5 out of 5 average rating, 162 reviews

A screened-in lanai features a heated saltwater pool surrounded by colorful outdoor furniture. Children’s toys and pool floats are placed nearby, alongside a small bike. The serene space is perfect for relaxation and play, with trees visible beyond the enclosure.

Home in Palm Harbor

Coastal Escape: Kid-Friendly Pool & Playground

★ Family-friendly Palm Harbor retreat near beautiful beaches - Honeymoon Island: 6 miles away - Clearwater Beach: 15 miles away ★ Heated saltwater pool ★ Screened-in lanai ★ BBQ grill ★ Large fenced backyard with playground ★ Outdoor dining area ★ 3 bedrooms with new mattresses - California king size bed - Queen size bed - Kid-friendly room w/ 2 bunk beds ★ Renovated kitchen and bathrooms ★ Open living space for family gatherings and movie nights ★ Toys, games and kid-friendly extras

A serene outdoor space features a sparkling pool framed by lush tropical landscaping. A relaxing spa is integrated into the pool area, accompanied by comfortable lounge chairs. A shaded cabana and grilling station are visible in the background, enhancing the inviting ambiance.

4.94 out of 5 average rating, 128 reviews

The Jungalow SOHO - Pool/Hot Tub

The Jungalow is the ultimate urban oasis. Enjoy the luxuries of the home or venture out to local attractions like the iconic Bayshore Boulevard, Historic Hyde Park, SOHO, Downtown and more. This home was designed with comfort and convenience in mind. Fully equipped with a smart tv, high-speed WIFI, pool and hot tub - this place is paradise. Central to the action - walk to unique rooftop bars, restaurants and shops or Uber to local attractions like Water Street, Amalie Arena, and the Riverwalk.

An open-concept living area showcases a modern design with a gray sectional sofa, a wooden coffee table, and a light accent chair. Abundant natural light filters through the windows, illuminating the kitchen and dining space equipped with contemporary appliances and minimalistic décor.

4.95 out of 5 average rating, 151 reviews

Rivers Edge Pool Home King Bed Near Downtown Parks

Escape to this bright, modern 3-bedroom pool home steps to the River in the heart of Seminole Heights! Perfect for up to 6 guests, this open-concept retreat features a private, screened-in backyard with a sparkling pool and BBQ. Enjoy a dedicated workspace and walk to local restaurants, coffee shops, and parks in this vibrant neighborhood. Centrally located just minutes from Tampa's top attractions including Downtown, Lowry Park Zoo, Armature Works, UT, USF, Bush Gardens, Raymond James, Ybor!

4.99 out of 5 average rating, 566 reviews

A cozy bedroom is highlighted by a spacious bed adorned with a patterned blue and white coverlet. Light-colored walls and exposed beams create a bright atmosphere, while a rustic cabinet and organized wooden crates add functional charm. A window offers natural light and views of the outdoors.

Farm stay in Plant City

Farm Experience~Family Fun~Animals~20 minTampa.

This unique find farm stay is an adventure! Hand feed cows, goats & chickens, explore the creek & garden, roast s'mores, drive a tractor, lay in the tree swing on our 5+acres! This peaceful oasis is more than just a place to sleep, it's a dreamcation. Located 8min to winery, 25min to Tampa, 45min to beaches/Disney. This barn farmhouse has a bedroom, loft, kitchen and bathroom. Everything you need for a family getaway. If you're looking to get away from the city and slow down, this is for you!

A private pool area features a heated pool surrounded by lush greenery and a patio area. Two lounge chairs with patterned cushions are positioned beside the water. A seating area can be seen in the background, along with a tasteful outdoor dining setup.

4.98 out of 5 average rating, 113 reviews

Historic Pool Home (heated pool) in South Tampa.

Our comfortable historic pool home was originally built as a Church. Now, it is a private oasis! We are 25 minutes from beautiful Gulf beaches, and only 1 hour from Disney. Busch Gardens is also less than half an hour away. Quick access to Raymond James Stadium. Enjoy our beautifully landscaped private pool, and walk to Starbucks and other local restaurants. Dogs welcome with pre-approval from your hosts. We would love to welcome you to our clean and cozy home. No cleaning fees! ;-)

4.98 out of 5 average rating, 263 reviews

Two wooden Adirondack chairs are positioned on a deck overlooking a serene lake. A floating dock extends into the water, featuring two red lounge cushions. The clear blue sky enhances the tranquil atmosphere, with greenery visible along the shoreline.

Cottage in Tampa

Bay Lake Cottage

You’ll have the Entire 500sq ft Cottage & private entry, deck/dock, all to yourself. Located on a 37-acre private ski lake. Key-pad entry, private parking. 1 king bed, 1 bath, queen sofa bed, washer/dryer, WiFi, smart TV’s, blackout curtains,shampoo,conditioner,hairdryer,WiFi. Fully stocked kitchen, smokeless grill, wine fridge upon request, k-cup/drip coffee machine. The lake has bass, we provide fishing poles/tackle box. Rentable Kayaks & Canoe. Dogs okay, sorry no cats, pet fee $50.

4.98 out of 5 average rating, 114 reviews

Bungalow in Tampa

Luxury Stay • Hot Tub & Heated Pool • Fenced Yard!

Explore the charm of this three-bedroom, two-bathroom bungalow – a luxurious haven where style meets relaxation. Enjoy moments of tranquility by the spa and screened pool, complete with inviting swim-up barstools, or unwind in the indulgent hot tub accommodating up to eight guests. Step into the serene outdoor oasis, adorned with elegant furnishings against the picturesque backdrop of a fenced backyard. Your getaway awaits, conveniently situated near the city's premier attractions.

4.99 out of 5 average rating, 150 reviews

Guesthouse in Tampa

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.

A spacious living area features a large sectional sofa with neutral-toned cushions surrounding a wooden coffee table. A textured area rug covers the hardwood floor, while a green wall adorned with plants and soft lighting adds a natural touch. A flat-screen TV is mounted on the wall.

4.94 out of 5 average rating, 154 reviews

Boho | TPA's Central Lux Zip Code | Pool Table

🌴 Boho 3-bed home in elite South Tampa ZIP. Fast Wi-Fi, fully stocked kitchen, and an outdoor lounge with TV & games. 🛏️ 3 Queen bedrooms 👶 Kid gear: crib, bath, gates & dinnerware 📺 55” Outdoor Smart TV 🚗 Free driveway parking for 3 📍 8 min to Downtown Tampa & ✈️ Tampa International Airport 💼 Perfect for families or work trips seeking style and convenience 💬 Need a longer stay? Message me directly for a special discount 🔜 Summer 2026: Hot tub, outdoor shower

A modern living area features a comfortable sofa and two upholstered blue chairs. A wooden coffee table with decorative items sits in the center. Light filters in through the window, illuminating the space, which is complemented by a neutral wall color and well-placed lamps.

4.93 out of 5 average rating, 147 reviews

Tampa’s Comfy Cozy Home - Location & Amenities

Your modernly updated & perfectly located home will provide everything you may need:★OUTDOOR RETREAT with Grill, Hammocks & Pond★CHEF'S KITCHEN fully equipped ★dedicated OFFICE/WORKSPACE★comfy & functional living, dining & sleeping amenities. Very desirable Tampa neighborhood with quick access to Downtowns Tampa or St. Pete, Westshore/Airport areas, MacDill AFB, nightlife/sports/shopping/entertainment venues and Bay area beaches. EV charging capability available