Family-friendly holiday rentals in Pinellas County

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.

4.97 out of 5 average rating, 108 reviews

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.

A screened-in pool area features a clear blue in-ground pool surrounded by lounge chairs and vibrant blue seating options. Lush greenery provides a natural backdrop. Sunlight filters through the mesh canopy, creating a bright and inviting space for relaxation.

4.94 out of 5 average rating, 183 reviews

Spacious Home+Guest House w/Huge Pool/Big parking

Enjoy this tastefully decorated home with a separate guest house, perfect for families or groups. Over 2500 sq ft with a huge backyard and pool, just minutes from beaches, theme parks, restaurants & shops. ✨ Highlights: Main house (3+2) + guest house (1+1) Huge backyard & private pool Family-friendly, perfect for gatherings Close to beaches, Splash Harbor Water Park, restaurants Large parking for 7+ cars/RV Convenient location Book your stay and enjoy comfort, style, and fun in one place! :))

5 out of 5 average rating, 154 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 saltwater pool & playground

★ 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

4.92 out of 5 average rating, 199 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!

4.97 out of 5 average rating, 157 reviews

[Top Pick] Family Fun Getaway | Heated Pool

Discover your ideal getaway, complete with all your dreams come true! Located just minutes from stunning beaches & conveniences, this fantastic home offers endless fun! From a heated pool, hot tub, and 2 person hammock, to a fire pit, BBQ, and a fully-equipped kitchen for your delight! Your family will be close to everything when you stay at this centrally-located home. 1 min to Largo Tennis Courts, Olympic size pool, baseball 8 min to Independence Square 5 min to beach 4 min to laundromat

4.98 out of 5 average rating, 163 reviews

The exterior of the home is surrounded by lush tropical foliage, including palm trees and native plants. A covered patio area can be seen, leading to a pathway of gravel that weaves through the vibrant garden. The inviting entrance is framed by greenery, creating a serene atmosphere.

Villa in Largo

Quiet 3BD Huge Tropical Garden & Patio. 5min Beach

Escape to our tranquil tropical paradise! Our private garden overflows with emerald palm trees, exotic foliage and native blooms, while the covered patio offers a place to relax and savor nature's natural sounds. Grill area, outdoor seating, lounge chairs. 5 minutes to Indian Rocks Beach and downtown amenities. Embark on bike rides on the nearby Pinellas Trail and Tailor Park with our complimentary bikes. Enjoy fun and fishing with our provided kayaks and gear, easily loaded onto your car.

5 out of 5 average rating, 206 reviews

A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.

Home in St. Petersburg

Beautiful Tampa Bay Pool Home Near Gulf Beaches

A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

A spacious outdoor pool area is visible, featuring a large swimming pool surrounded by lounge chairs and seating areas. A pergola provides shade, while decorative planters add greenery. The area is enclosed by a privacy fence, creating a secluded retreat.

4.98 out of 5 average rating, 367 reviews

UTOPIA!Heated Pool &Hot Tub 2 master suites w KING

UTOPIA best describes this perfect single story VACATION HOME ! 5 MINUTE DRIVE TO BEACHES!! HUGE AMAZING RESORT SYTLE FREE HEATED POOL with LUXURIOUS PERGOLA, HOT TUB , TIKI BAR and plenty of outdoor seating perfect for soaking up the Florida sun ! Large 3 bedroom 3 bath pool home. Pool heat starts Oct 15 and runs thru april 15 seasonally for FREE( heats 80-85 degrees) large four person hot tub is hot and ready at 101° upon your arrival. No waiting on a hot tub to heat up!

Superhost

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, 303 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 bright living room features a large gray sofa adorned with colorful cushions. A light wood coffee table sits at the center, while a flat-screen TV is mounted on a white unit. Natural light illuminates the space through sliding glass doors, leading to a backyard.

4.92 out of 5 average rating, 117 reviews

Cozy home minutes from the beach

Welcome to our warm and inviting Airbnb home, your personal sanctuary in sunny Largo, Florida. Our prime location grants easy access to the breathtaking Gulf of Mexico beaches, just minutes from Clearwater and St. Pete. The area offers amazing parks, charming boardwalks, delightful dining, and countless golf fields. It's a great place for water sports and adventure-seeking. We can't wait to extend our warmest welcome, ensuring that your stay is truly unforgettable!

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, 139 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.