Family-friendly holiday rentals in Pinellas County

The inviting pool area features a heated pool with clear turquoise water, surrounded by lounge chairs and a spacious pool deck. A dining area and outdoor kitchen can be seen, with a large TV mounted on the wall, creating a welcoming space for relaxation and entertainment.

4.97 out of 5 average rating, 180 reviews

Palm Oasis | Heated Pool | Near Beaches

Enjoy a fun filled family vacation or a relaxing getaway with friends at this stylish, newly remodeled 3-bedroom 2-bath pool home, conveniently located between Clearwater and St. Petersburg. The home is very close to plenty of restaurants, shopping, and Beaches. Tampa is approximately a 30 min drive to Tampa away, offering more dining, shopping and adventure. This home has everything needed from quality mattresses to kitchen essentials and “Smart TV’s” in every room. Must be at least 21 to book.

Aerial view of a tropical backyard featuring a shaped pool with floating loungers. Surrounding the pool, lounge chairs with umbrellas are positioned next to a wooden deck. The yard is covered in turf, and there are colorful pool toys and deck furniture visible.

4.99 out of 5 average rating, 126 reviews

Best Celebration - Heated Pool - Hot Tub - Arcade

🌴 𝐇𝐨𝐮𝐬𝐞 𝐨𝐟 𝐏𝐚𝐥𝐦𝐬 | 𝐘𝐨𝐮𝐫 𝐏𝐫𝐢𝐯𝐚𝐭𝐞 𝐅𝐥𝐨𝐫𝐢𝐝𝐚 𝐏𝐚𝐫𝐚𝐝𝐢𝐬𝐞 ☀️ Escape to a stylish tropical retreat perfectly located near Florida’s best beaches, attractions, shopping, and dining. Ideal for families, groups, or a relaxing getaway, House of Palms offers comfort, privacy, and everything you need for an unforgettable Florida stay. 📍 5 mins – Shopping & dining 🏖 15 mins – Gulf beaches 🌊 20 mins – Clearwater 🌆 25 mins – Downtown St. Pete ✈️ 30 mins – Tampa Airport

Guest favourite

An outdoor patio area features a dining table adjacent to a heated pool. Lounge chairs are positioned nearby, under a screen enclosure. The pool is framed by a laid stone surface, with a view of lush greenery beyond the surrounding fence.

Villa in St. Petersburg

Heated Pool! Huge Walk In Shower! 5 min to beach!

Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

4.95 out of 5 average rating, 159 reviews

4.97 out of 5 average rating, 153 reviews

Clearwater Gem! XL-Pool | Courts & More!.

Welcome to The Quazzi House, a private ½-acre tropical escape designed for fun, relaxation, and unforgettable memories. This unique 4BR / 3BA home features a 40-ft pool, private hot tub, pickleball & basketball court, and a spacious backyard perfect for families and groups. 📍 15 min to Clearwater Beach 📍 20 min to Tampa 📍 10 min to PIE Airport Ideal for large families or groups looking for an active, resort-style stay in sunny Fl! NO PARTIES — $1,000 fine & cleaning fee strictly enforced!

4.98 out of 5 average rating, 121 reviews

Home in Pinellas Park

The Guest House

The Guest House is a coastal themed 2100 sq ft house, split floor plan, 3 bedrooms & 2-1/2 baths for sleeping 6 comfortably. The Guest House is nestled in a quiet neighborhood in Pinellas Park, FL & is a favorite family vacation get-a-way close to beaches & attractions. Enjoy the Master Suite with an adjustable Sleep Number king bed & Master Bath with garden tub, shower & walk-in closet. After a day of enjoying the beaches or attractions, relax, & unwind on the private screened lanai.

Guest favourite

4.93 out of 5 average rating, 123 reviews

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

Welcome to Clearwater Tranquility- Our unique space offers endless amenities and fun! With over 5000sq ft there's room for the whole family to enjoy. Most rooms have a view of the yard &pool! Inside includes a movie theatre, 3 dining spaces, 2 living rooms, 2 primary bedrooms, game room, yoga studio,arcade games, home gym/sauna and a wet bar to make your favorite cocktails or juices. Outside presents an Olympic sized swimming pool, pickle ball, mini golf, outside dining, fire pit &more

Superhost

4.86 out of 5 average rating, 104 reviews

Putt Putt! | 3 bed | Large Pool | Private Yard

Welcome to our Coastal Boho Oasis with a pool and a fenced in large backyard, just a short 12-minute drive from the pristine shores of Indian Rocks Beach! Step into a world of serenity and style in this newly renovated coastal retreat that perfectly blends modern comfort with bohemian vibes. This home is furnished with all of your family’s needs, from a pizza cutter to a pack and play. Come, enjoy and relax. The spacious backyard includes a fire pit and lounge chairs around the pool

4.98 out of 5 average rating, 237 reviews

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

Guest favourite

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!

4.9 out of 5 average rating, 314 reviews

4.98 out of 5 average rating, 160 reviews

Family Resort | Heated Pool + Hot Tub + Games

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.

4.95 out of 5 average rating, 150 reviews

Artsy oasis in Clearwater

This centrally-located Clearwater house is just a short drive to beaches, airports, Dunedin, and downtown Tampa. This single-family home has a private in-ground pool, screened in porch, pergola, fire table, outdoor shower, and a variety of flowering plants. There are 2 bedrooms and a bonus room. There is a queen bed in each bedroom, bunkbeds in the bonus room, and two queen sofa beds in the living room. Pet and family friendly.

An inviting outdoor space features a heated pool and a shaded area adorned with cafe lights. Two hanging egg chairs and comfortable seating arrangements complement the modern wooden furniture. The stylish striped rug enhances the atmosphere, while the pool's tranquil blue water is visible in the background.