Family-friendly holiday rentals in Hillsborough County

Tiny House Oasis Blue Vatican . Near MacDill Base

Enjoy this small and beautiful Oasis, a perfect hideaway to forget about the noise of the city, relax with the aroma diffusers and your favorite music; In the mornings fall in love with our solarium while having a good coffee. We are located in South Tampa just 3 minutes away from the MacDill Airbase. 5 min Picnic Island Park, 10 min Port Tampa Bay Cruise and Downtown, 15 min International Airport. 15 min Raymond James Stadium, 40 min Clearwater Beach. Free Parking for up to 2 cars.

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! ;-)

Home away from Home

Our 1100 sf Home Away from Home has been completely renovated from head to toe! It's also 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? As the day ends, enjoy a glass of wine on the back patio or take a sunset walk along the Hillsborough river, across the street at Rivercrest Park.

Gasparilla Bayshore Good Vibes cottage

Great location for this cottage one block from Infamous Bayshore Blvd. Smart Tv's and quiet back porch with fire pit makes this location perfect for vacationers. Short walk to Bayshore blvd with scenic views of downtown Tampa and beautiful Tampa Bay water ways. Come and enjoy biking, running, skating or just walking along this 4 miles continuous waterfront walkway. You will have views of Tampa Bay on one side and views of multi-million dollar homes on the other during your stroll.

FLASH SALE! 3bd Near Bayshore |King beds| Pets ok!

🚨Special Offer: We’re running a limited-time Flash Sale for select dates! Message us to unlock exclusive savings for your short term or mid term stay‼️ 🏡Charming 3BR/2BA bungalow just 1 block from Bayshore Blvd — Tampa’s iconic 4.5-mile waterfront linear park! Enjoy the whole home to yourself: relax on the screened porch, sip wine in the clawfoot tub, grill out, or play in the backyard. Walk or bike to parks, restaurants, and Tampa’s top spots. Book your bay stay now! 🌴🚲🛁

Life in a Shipping Container!

Peace and quiet on a small country farmstead. Off the beaten path yet conveniently located halfway between Disney World and Clearwater Beach. Historic Plant City, famous for their strawberry farms, has a cute downtown area with antique shops, bistros and cafes. Relax on your private back deck overlooking our organic vegetable garden. Say good morning to a variety of birds (including welcoming our newest chicks) living on the property and goats, cows and horses living nearby.

The Ashley Fun House - Tampa, Fl

Welcome to the Ashley Fun House! We have lots of family friendly activities and pet friendly. Located 10 minutes from the Tampa Airport, 10 minutes from downtown Tampa and Riverwalk, 3 miles from Busch Gardens/Adventure Island, 1.3 miles from Lowry Park Zoo, 5 miles from Tampa Bay Bucs Stadium, 6 miles from Amalie Arena. Please understand the house is located in an urban area of Tampa so the area may be a little noisy on the weekends and very seldom during the week.

Tiny Tulum | Tropical Oasis in Tampa’s Heart!

Welcome to Our Romantic Tulum-Inspired Retreat! Escape to a tropical paradise at our enchanting Tulum-inspired oasis, designed with romance and relaxation in mind. Nestled in a serene neighborhood, our beautifully decorated retreat offers the perfect blend of luxury, comfort, and bohemian charm, creating an idyllic getaway for couples seeking a memorable experience. Why book a generic Airbnb when you can book a hand crafted Tropical Paradise?

Centrally Located - Early Check In

Charming Tampa retreat in a national historic district! Your cozy carriage house is near I-275 & I-4, 10 min to TPA Airport, Busch Gardens, Ybor City, Downtown, USF, and Moffit. Enjoy the walkable neighborhood, a park one block away, and great restaurants and breweries. It is perfect for exploring Tampa’s top attractions; 35 min to Gulf beaches and Orlando in 70 min. Comfortable, private and ideal for couples or small families.

Lakeview Retreat with Private Pool Perfect Getaway

Welcome to our charming Tampa retreat! This newly renovated house has been carefully designed with an open layout, it features 2 bedrooms and 2 full bathrooms. The highlight of this home is undoubtedly the patio area, beautiful outdoor furniture, and an amazing pool with a stunning and unique view of the lake canal. The location is perfect, everything is nearby with quick access to major highways such as I-4, I-75, and I-275.

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

☀️ Looking for a place the whole family/group can enjoy? This centrally located modern home is full of fun and style, with everything you need—from a fully stocked kitchen 🍽️ to beach supplies ⛱️ and more. Enjoy an Insta-worthy space with 5-hole mini golf, giant outdoor games, a heated pool, arcade & board games, and cozy spaces inside and out. 📍 Just 6 miles to the beach and Downtown St. Pete—perfect for your getaway!

Little Manatee River Cottage

This cottage is located on the Little Manatee River. Sun City Center 10 min, Moffit Cancer Center 3 miles. Abundant fishing charters, manatee viewing center and Simmons Park all within minutes. Fully furnished, linens, kitchen utensils; bath towels; blankets pillows comfy furnishings. View sunsets from the dock or front sitting area.