Family-friendly holiday rentals in Pinellas County

A covered patio area is visible, featuring comfortable wooden chairs with blue cushions and a wooden table. The scene is framed by a screened enclosure, providing an unobstructed view of a private pool surrounded by lush tropical plants.

4.89 out of 5 average rating, 302 reviews

Quiet 3 BD Large Heated Pool & Terrasse-5 mn Beach

Unwind and relax while staying at our freshly renovated Floridian nest! Pretend you are lost in our tropical garden while diving in the pool, take some time for yourself on the covered patio directly facing the blue water and the vivid green of the palm trees. Just breathe, your favorite meal smells good on the grill and your family is enjoying the large TV in the comfortable open space with high ceilings! Enjoy the sea, you are a 5 min drive from the beach and close to everything. Feels good!

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.

4.98 out of 5 average rating, 129 reviews

JOJO'S Beachside 1Acre Estate-New 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.

5.0 out of 5 average rating, 170 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: 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

A spacious living area is highlighted by large glass doors that open to the pool area. The room features modern furnishings, including a comfortable gray sofa and a hanging chair, with natural light enhancing the neutral decor.

4.96 out of 5 average rating, 150 reviews

Lavish Heated Saltwater Pool Home Mins. to Beach

Paradise awaits in this stunning & pristine 4-BR heated saltwater pool home! Centrally located to many restaurants, stores, and entertainment while only 4 mins from the beach! Private backyard and huge covered patio deck that wraps around the pool. Gracious updates throughout with all of the amenities for a perfect vacation—from the relaxing outdoor lounge space and BBQ grill to the expansive dining table for 12, bars, TV's, firepit, and even an outdoor ping-pong table for hours of family fun!

An inviting pool area features a clear blue pool alongside a spacious hot tub, both surrounded by a grey stone deck. Comfortable loungers are arranged under an umbrella, offering shade. Sunlight filters through the screened enclosure, creating a bright and open atmosphere.

4.92 out of 5 average rating, 131 reviews

Heated Pool and Spa | 5 min to beach

Welcome to our home in Largo, Florida. This is a modern and comfortable place with a heated pool and spa, just minutes from Clearwater and Indian Rocks beaches. The kitchen has everything you need, and the living spaces are meant for relaxed stays with family or friends. The house has 3 bedrooms and 2 bathrooms and sleeps up to 6 guests comfortably. Whether you spend the day at the beach or by the pool, you’ll have an easy place to unwind and enjoy your time here. We hope you feel at home.

4.98 out of 5 average rating, 117 reviews

Casa Flamingo - Private - Outdoor Bar+TV - Games

Welcome to Casa Flamingo where guests "flock" to get away & relax in privacy. Guests will love the central location of this home but also the private oasis the backyard provides. Surrounded by mature palms & native plants guests will experience true Florida living and take advantage of the beautiful weather with an outdoor bar + TV, heated pool, a hammock and more. Just 8 minutes to the beach & within walking distance to Target, Publix & more the Flamingo House is your home away from home.

4.94 out of 5 average rating, 126 reviews

🍍Beautiful Home Heated POOL 5min to BEACH. 8 ppl🍍

Welcome to your beautiful and spacious rustic coastal-style oasis! Perfect for up to 8 guests. This immaculate updated home is located in Rustic Pines - a quiet area close to Indian Rocks Beach and the new Seminole Shopping Center. Enjoy your private backyard with a pool and luscious landscaping. Walk to shopping, dining, entertainment, and park with trails. 7 min to Largo Golf Course and only 9 min to Splash Harbor Water Park. Every effort has been made to make your vacation memorable!

4.98 out of 5 average rating, 231 reviews

Home in Clearwater

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

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.

4.9 out of 5 average rating, 313 reviews

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!

A serene outdoor space features a heated saltwater pool surrounded by a screened enclosure. Lounge chairs are positioned poolside, and a children's swing set is visible in the background. The vibrant sunset creates a warm ambiance over the tranquil setting.

4.96 out of 5 average rating, 153 reviews

Sleeps 8 Near Beach | Pool + Game Retreat

Discover your tropical retreat at Paradise Palms in Seminole! This newly renovated, pet-friendly home features a game room, outdoor dining, and a sparkling, saltwater swimming pool - with heating provided at no extra cost. mid Oct- April. Just minutes from Madeira Beach, we've equipped you with all the beach essentials for your convenience. Professionally hosted by Tropical Oasis, FL, we've meticulously prepared all the essentials to ensure a memorable stay.

4.95 out of 5 average rating, 174 reviews

10 Min to Beach | Heated Pool, Hot Tub, Arcades

Create unforgettable memories at this fun-filled family retreat just 10 minutes from the beach! Spend your days swimming in the heated pool, relaxing in the hot tub, grilling on the BBQ, and gathering around the fire pit under the stars & string lights. Challenge the family to arcade games, axe throwing, soccer game, giant 4 in a Row, giant X & O, and more. Close to beaches, shopping, restaurants, and attractions, it's the perfect Florida getaway.

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