Family-friendly holiday rentals in Pinellas County

Tropical Pool Resort– Close to Beach, Lake, Golf

Relax in this spacious 4BR pool home near Florida’s sandy beaches & Lake Seminole Park! Safe and Ready! Enjoy a private fenced yard and pool, tropical landscaping, and plenty of space for family, work, or play. Just minutes to golf, tennis, dining & top attractions. Perfect for vacations, snowbirds, or remote work with 2 desk areas including one standup desk, a stocked kitchen & fun extras like bike, beach gear & fitness space. Ask about special promotions then book your tropical retreat today!

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.

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

The Oasis | Heated Pool - Arcades - Mini Golf

Staying at The Oasis is the perfect blend of vacation and home. Every detail was carefully thought out to provide guests two things: comfort and fun. The ULTIMATE vacation awaits you. Whether a group of friends or your family vacation, this home was designed with relaxation AND fun in mind. Located within walking distance to Largo’s beautiful Central Park and a few miles to the beach, you can spend the day exploring the area or truly relax in the resort style, private backyard. BUT! No parties

[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

Modern Cozy 3BR | Walk to IRB Beach + Heated Pool

Experience luxury and comfort in this fully remodeled 3BR home, just a 10-minute walk to the beach. Enjoy a brand-new saltwater heated pool, an open-concept floor plan, and spacious screened porches. The home boasts a modern kitchen, updated bathrooms, new flooring, and a new roof. Fully stocked with all essentials for a seamless family vacation, from kitchen tools to beach gear. Relax in the screened outdoor lounge and dining area for the perfect retreat. Max 6 guests | No pets allowed

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

Kick back and relax in this calm, stylish beach-vibin home. The 2 bedroom plus queen size sleeper sofa in sunroom is the perfect spot to get away and never have to leave. Enjoy your morning coffee or afternoon cocktail lounging by the fire pit. Light up the grill and cook your meal while you enjoy a pool heated to 86 degrees for free! Wifi and 3 streaming TV's. If you want to get out and explore, you are only 6 minutes from the award winning beaches and 25 minutes from downtown St Pete.

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.

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.

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

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.

4BR-Heated Pool-Sauna-Fire Pit-Beach<5 Min-Theater

Welcome to Seminole Shores Villa, your 2,400-sf tropical spa oasis! This property is a 4BR home with tons of amenities to make your stay truly memorable. While the beaches are close (<5 min), you might never want to leave the heated salt-water pool nestled into a huge spa-like backyard, which offers plenty of privacy and activities. This house was completely renovated in 2023 to incorporate a tropical design. We prioritized a clean and safe environment as part of your experience.