Family-friendly holiday rentals in Pinellas County

4.97 out of 5 average rating, 101 reviews

A spacious backyard is featured, showcasing a heated saltwater pool surrounded by a large paver deck. Lush green grass fills the area, bordered by well-maintained landscaping. Tall trees provide shade in the background, contributing to the serene outdoor environment.

Home in Seminole

JOJO'S Beachside 1Acre Estate-New Heated Pool

LUXURY CUSTOM HOME WITH NEW HEATED SALTWATER POOL ONLY 1.5 MILES TO BEAUTIFUL WHITE SAND REDINGTON BEACH ON 1 ACRE OF LAND. HOME HAS JUST BEEN TOTALLY RENOVATED WITH TASTEFUL FINISHES. THIS AREA IS VERY QUIET AND UNIQUE FOR PINELLAS COUNTY WITH LARGER LOTS AND HOMES. 2300 SQUARE FEET WITH HIGH VAULTED CEILINGS. LARGE OPEN KITCHEN, T.V.'S IN EVERY RROM. GREAT LOCATION JUST MINUTES FROM: COFFEE SHOPS , GROCERY STORE, SHOPPING, RESTAURANTS, MOVIE THEATERS AND PARKS. LARGE PAVER DECK BY POOL AREA.

4.98 out of 5 average rating, 164 reviews

A private outdoor space features lush greenery framing a stone pathway leading to a wooden seating area. The area is adorned with tropical plants, creating a serene ambiance. A small bar-height table with stools is visible in the background.

Bungalow in Oldsmar

salt living at its best

- Resort Style Water front - Stand alone - Hot tub - Sunrise / sunset views on dock - free Kayaks - Internet / YouTube cable - 65” smart TV - Spacious Bedroom with king size bed, walk in closet and flat TV - Washer and Dryer in unit - Designated work space -Pet friendly - Fenced private patio - Free 2 cars / Boat Parking. - Central location ( beaches, restaurants, Tampa, St Pete’s, safety Harbor, Dunedin - 11 minutes from Ruth Eckerd event Hall - Pristine clean - Coffee station - Dining area

4.92 out of 5 average rating, 196 reviews

The Palm House | Free Heated Pool!

Come enjoy our newly renovated pool! Our updated home is ideally situated just a few minutes from local beaches, restaurants, and entertainment, making it a perfect home base for your Florida visit. The backyard boasts a newly renovated heated pool, outdoor shower and screened patio. Our bright living room offers a comfortable space to unwind after a long day, and our kitchen is fully stocked with cookware, utensils and a coffee station for your convenience. Updated pool pics coming soon!

4.98 out of 5 average rating, 291 reviews

TIKI Bar+SAUNA+HOT Tub+Heated POOL! 2 KING beds!

If you like pops of color, modern decor a FREE HEATED pool seasonally Oct 15-April 15 (80-85 degrees) HOT TUB , RARE SAUNA, TIKI BAR fire pit and everything new then this house is for you! BRAND NEW HOT TUB installed 4/2025!!! Very Close to shopping and beaches perfect dedicated vacation home! We are family owned and operated and dedicated to you and your vacation experience. Message me if you have any questions! SUPER FAST WIFI 753Mbps - (1 G if you plug into modem) verified by Airbnb

4.88 out of 5 average rating, 154 reviews

A welcoming living area features light-colored seating with orange and gray accents. A wooden coffee table is centered on a decorative rug. Natural light filters through the vertical blinds, illuminating the room's neutral tones, complemented by a potted plant and wall-mounted lighting.

Home in St. Petersburg

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

A welcoming porch area is seen, featuring two white rocking chairs and a small side table. Lush greenery and blooming flowers surround the space, while a door leads inside. Light reflects off the stone flooring, complementing the vibrant green walls.

4.98 out of 5 average rating, 108 reviews

Walk to beach shops food drinks “The Inbetween”

This is one of Island Rum Suites collection! Stay with us to see why we are one of the best family owned and operated around! We are in a quiet and safe neighborhood, walking distance to the beach, shopping, restaurants, nature parks, water park, pizza, pubs and ice cream! All guests must be listed on the reservation in order to be on the property and accounted for, even children. Zoning allows 2 people per bed and 2 cars No pets allowed Florida State License # DWE6215889

4.91 out of 5 average rating, 299 reviews

A modern living area features a large sectional sofa adorned with decorative pillows. A round coffee table sits at the center, displaying a small plant and snacks. Bright red chairs are positioned near a window, complemented by a light and airy ambiance from natural light.

Home in Seminole

Beachy Home Minutes from sugary sand beaches

Sunny Florida Beach Home! 4 minutes drive to the #1 best beach in America nominated by Trip Advisor, where you will find beautiful white sand and extremely warm and clear water! Enjoy tons of top local restaurants and entertainment all minutes from your door in this relaxing, low key beach neighborhood. Super kid friendly! Games, BBQ, swing set, Apple TV, and bikes for the whole family! Enjoy the entire house that has been completely remodeled and is sparkling CLEAN!

4.96 out of 5 average rating, 164 reviews

A well-appointed bedroom showcases a spacious bed with decorative pillows and clean, folded towels arranged neatly. Soft bedside lamps provide gentle lighting, while textured wallpaper adds warmth to the space. Closet doors are visible in the background, enhancing the room's functionality.

Flat in Largo

LOVELY & SUNNY Condo 6 Minutes from the Beach!

You will love this first-floor unit! Bright, spacious and updated condo just a 6-minute drive to Indian Rocks Beach! Also nearby are various parks with trails and picturesque greenery. As well as close by there are several restaurants, grocery stores. Beautiful and interesting cities such as Clearwater, Tampa and St. Pete are just a stone's throw away, this is a paradise for everyone! This complex has a pool, gas BBQ for grilling, laundromat and free parking.

4.9 out of 5 average rating, 162 reviews

The outdoor space features a heated pool surrounded by eight sun loungers, umbrellas, and a BBQ area. Inflatable floats rest on the water, while a spacious patio holds dining tables and chairs. Lush grass surrounds the pool, enhancing the inviting atmosphere.

Home in Seminole

8 Min to Beach! Heated Pool, Fire Pit, Game Room

Just a short drive to the beach, this home has all the entertainment you could ask for! Heated pool, game room, pool table, arcade games, fire pit, mini golf, and much more! This tropical villa is in a great, quiet location within minutes to some of the most beautiful beaches in the country. A true dream vacation! 4 min - Walsingham Park 6 min - Beautiful beach access 20 min - Clearwater 30 min - Tampa Experience Seminole With Us & Learn More Below!

4.98 out of 5 average rating, 126 reviews

[Top Pick] Family Fun Retreat | Heated Pool

Welcome to your vacation paradise! This stylish home is perfect for family fun and relaxation. Enjoy modern comforts, a spacious living area, a well-equipped kitchen, and 4 cozy bedrooms. Outside, epic games room with arcade games, football, basketball: or, unwind by the pool or soak up the sun in the private yard, with a full screened in area & tiki bar! With nearby attractions for all ages, this is your ideal base for a memorable family getaway.

5 out of 5 average rating, 224 reviews

A small outdoor seating area is depicted, featuring two bright green chairs and a matching table adorned with a potted plant. Lush green foliage rises around the space, creating a tropical ambiance. The background showcases a wooden fence and natural elements.

Guest suite in Largo

Cozy Private Bedroom Suite Private Entry King Bed

Spacious private master bedroom suite with private entrance and driveway! King bed. Private spacious bathroom! Fridge, microwave, Keurig coffee maker. Located in a large home. No access to the rest of house. 5 miles to Indian Rocks Beach. 8 miles to Clearwater. 2.5 miles to Botanical Gardens and Heritage Village, both FREE! 30 minutes from Tampa airport and 20 minutes from Clearwater St Pete airport.