Kid-friendly holiday rentals near Siesta Beach

King / Child Friendly / Near DT / Plunge Pool

Add us to your wishlist by clicking the ❤️ Unwind at our modern beach house near everything Gulfport & St Pete have to offer! Just over 1/2 mile away, head to dt Gulfport w/ its variety of restaurants, bars, breweries, coffee shops & boutiques. Gulfport's public beach is just a mile down the road, and other St Pete Beaches are a short car ride away. Don’t miss other nearby attractions like the St. Pete Pier and Dali Museum. This house is perfect for a couple's getaway or a fun family vacation!

Riverwalk-Parks-Museums-Skate Park-Manatees-Rest's

If you're ready to experience old Florida charm, our 2 story historic home is ready to offer to good ole southern hospitality. Located in the heart of our revitalizing downtown, there's never a dull moment. A welcoming front porch, with rockers for afternoon lemonade. Inside find spacious accommodations. Bike to the nearby riverwalk, privacy screened pool, and much more. Our home is the perfect space for your next family occasion - whether getting ready for a wedding, or just getting away.

Private family friendly home near beach!

Just 10 minutes to world class beaches, and downtown St. Petersburg! Our family-friendly home is located in Pinellas Point; the safest neighborhood in St. Pete, with beautifully kept houses and streets perfect for walking & biking. Parks less than a mile away have playgrounds and fishing piers. Our prime location offers easy access to St. Pete Beach & Fort De Soto Park, without any traffic. Minutes away from unbeatable St Pete dining. House is filled with baby+kids items to make travel a breeze.

Pure Bliss-Pool, Treehouse, Beach - 6bd/3ba

Relax in this stunning mid-century modern house near the beach with NEW saltwater pool with stone deck & splash pad/sun deck! Make your own childhood dreams come true for the kids with a backyard treehouse that is sure to make lifelong memories! This palm oasis is sure to please everyone! We have thought of everything, including all the vacation essentials for home, pool, & beach! Don't miss your chance to relax on America's favorite beaches at Anna Maria Island & Siesta Key- just minutes away!

Summer Discounts Available! Steps from the Beach!

Welcome to Your Dream Beach Getaway! Steps (one block!) from the sugar-white sands of Holmes Beach. We provide bikes, paddle boards, and all the other beach gear you will need for fun in the sun! Nestled in a quiet beachside community on the famed Anna Maria Island, this newly renovated home is ready for your dream vacation! Enjoy the shared HEATED pool or stroll to shops, restaurants, and the vibrant attractions of Anna Maria Island— a quick bike or trolley ride away. Perfect for families!

5 minutes to private Siesta Key Beach + 2 pools

Best getaway, beach vacation, and staycation! The luxurious condo is on the 1st. floor and located on Siesta Key in a tropical setting. It is kid-friendly and has private access to its private beach on Siesta Key Beach within 5 minutes of walking distance (the Best Beach in the U.S.A.) with crystal white sand and turquoise waters of the Gulf of Mexico. There are two heated pools, barbeque areas, lighted pickleball and tennis courts, a fishing pier, a gym, and a sauna, all for your enjoyment.

The Cottage at Central Park II

If you are looking for the perfect family home to cater to your every need, then look no further! With plenty of space to spread out, natural light that pours into every room, an expansive and private fenced in yard, screened-in porch and outfitted kitchen- this is the perfect place to entertain AND relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota in one of the areas most sought after neighborhoods you are in the middle of it all!

Pickleball! Pond! Private Heated Pool! Foosball

Welcome to Once Upon A Pond, by Stayawhilewithus! If travel is on the horizon, set your sails to luxury and tranquility at this newly updated 4BR/3BA getaway. The heated private pool offers gorgeous vistas of the pond in the backyard, so take your relaxation to another level with the scenic views and some mesmerizing bird watching. And don't forget to enjoy the pickleball court in our side yard - it'll be great fun for the whole family!

Cottage Getaway 2 miles from Beach

Cottage style decor. Private fenced backyard with screened porch, outside eating, gas grill & hammock. Laundry room with washer & dryer. Shopping, grocery store, movie theater & lots of dinning choices 1-2 miles. Easy parking in driveway. Very Convenient location. The #1 Beach is 2 miles away. ***Please note this is a NON-SMOKING & NON PET home***