Family-friendly holiday rentals in Hillsborough County

Bayshore - Pool - Outdoor Kitchen - Yard

Get away in elegance and soak up the South Tampa sun in this gorgeous 4 bedroom, 2 bath pool home. Visit with family and friends in the covered patio and pool area, cook in the outdoor kitchen or relax with a drink by the pool (not heated). Enjoy great restaurants or visit one of the many attractions nearby - The Aquarium, Armature Works, Sparkman's Wharf, just to name a few. Visit Bayshore Park Fitness Trail, just minutes away and explore the 4.5 miles of waterfront views. Enjoy all of Tampa!

Family · Kitchen · Getting around

Coastal Escape: Heated Pool, Playground&Family fun

★ 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

Indoor spaces · Family · Bathroom

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.

Indoor spaces · Kitchen · Location

The T and C Club

Welcome to The T and C Club! A featured home for the Make-A-Wish Foundation. Located 6 miles from the Tampa Airport, 7 miles from Raymond James Stadium and only 15 miles from award winning Clearwater Beach, this home is convenient as it gets. Completely refurbished, there is plenty of space to sleep 10 individuals comfortably, dining table for 10, a large resort-like backyard, saltwater pool, propane grill and all the fun you can imagine. This will truly be a case of you won’t want to leave!

Kitchen · Indoor spaces · Getting around

Waterfront Pool Oasis Kayaks, Games & Beach Vibe

Relax at your waterfront oasis in Apollo Beach with a private pool, kayaks, and sunset views. Spot dolphins and manatees from the backyard or unwind on loungers with outdoor dining and games. Inside: full kitchen, dining area, 2 bedrooms, 2 baths, plus an extra living room with sleeper sofa and closet that serves as a 3rd bedroom. Close to Tampa, beaches, dining, and family attractions — ideal for families, friends, or a romantic getaway in a spacious private home. LIC# DWE3913431

Indoor spaces · Family · Accuracy

Elegant 5BR Historic Gem w/ pool, walk to Bayshore

Luxury design in South Tampa! This 5 bedroom, 3.5 bath, 1923 home blends historic charm with an upscale interior. It’s perfectly located just 2 blocks from Bayshore Blvd, near Hyde Park, and minutes from Downtown, Riverwalk, and UT. Enjoy memory foam beds, organic cotton linens, 2 King suites, 2 California King rooms, 2 twins (with the option to convert to a King) custom sofas, and thoughtful designer finishes. A refined, comfortable base in Tampa’s most walkable, sought-after area.

Kitchen · Family · Parking

Specious home W/ Heated Pool ! ! ! Great Location.

Cozy, spacious home 🏡 w/ heated swimming 🏊‍♀️ pool, next to a golf ⛳️ course. Close to the famous beaches ⛱️, St.Pete and Tampa. This cozy open home has a large living room, big kitchen and pool deck patio. All 3 bedrooms have large TV's. The big back patio has a swimming 🏊‍♀️ pool, TV, fridge and BBQ for cook outs & R&R. Located in a quiet family-friendly neighborhood. Location! 15 min - Clearwater Beach, Dunedin, Safety Harbor 30 min from - St.Pete, TPA Airport, Tampa

Indoor spaces · Family · Amenities

Villa Paradise

Relax with family in this quiet place to stay. Spacious house to enjoy with family and friends, enjoy a beautiful pool and a very large backyard, outdoor kitchen (only for 6 people). NO MORE THAN 6 PEOPLE. I do not allow events. You do not have access to the garage. I live in an apartment that I have in the garage. I do not have access to the accommodation from anywhere while the house is reserved. I am informing you of this for my safety and peace of mind. Thank you.

Family · Indoor spaces · View

Lemon House near Downtown Tampa

Settle in at The Lemon House, our 1949 2/1 bungalow, offers a central location to all of what Tampa offers. North Hyde Park is minutes from UT & Tampa’s Downtown scene: Armature Works, Riverwalk, Historic Hyde Park, The Heights & Bayshore. Prime for conventions, concerts, the port, sport attractions, Zoo, Aquarium, Busch Gardens & Beaches (30mins). Overall central for an eclectic variety of restaurants, parks, breweries and nightlife.

Family · Kitchen · Heating

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.

Indoor spaces · Family · Decor

Insta Worthy Retreat -HTD Pool- Arcade Room- 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!

Indoor spaces · Family · Location

WOW Clearwater Resort! Heated Pool, Pickleball

Welcome to your own private resort in Clearwater! In an amazing location just 5 minutes away from some of the most beautiful beaches in the country, you will have all the fun & entertainment you could ever need, right here at home! Heated pool, mini golf, basketball, pickleball, & more will give you an unforgettable vacation! 5 min - Beautiful beach access 8 min - Seminole City Center 20 min - Clearwater 30 min - Tampa

Indoor spaces · Family · Layout