Kid-friendly holiday rentals in Siesta Key

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.

Sunny Sarasota Vacation Home - VR2400236

Quiet Neighborhood - Single Private Home, Great Location! This beautiful home includes 3 bedrooms, 2 bathrooms and sleeps up to 10 people. Near #1 Rated SIESTA KEY BEACH & LIDO KEY BEACH. Come and relax in this newly renovated home. Large living room, dining room and lanai to accommodate your friends & family. 5 TV's, DVD players, Cable, Internet. Fully equipped kitchen & laundry. Bus stops, grocery stores & restaurants are near by. Base rate covers 6 guests; $20.00/night/additional guest.

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.

Coastal Cottage Near BEACH & downtown St Pete

This gorgeous listing is a newly renovated modern cottage with three bedrooms, two bathrooms, modern kitchen and dinning room. Fab location! 6 min drive to beach, 11 mins to the Rays Trop stadium, 13 mins to downtown St Pete. St Pete Beach (6 min drive) voted Trip-advisor 4th Best Beach in the World 2020 & Best Beach in USA 2020! We recommend this property for 4-6 adults and 3-5 kids. Perfect for groups, couples, families & biz travelers. Cleaned by professional company.

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!

Charming Sarasota Home with Pool!

Charming 3/2 home with a pool! very safe neighborhood, 8.9 miles to Siesta Beach and 5.5 miles to Lido Beach. 15 minute walk to The quaint little village of Pinecraft and Der Dutchman Restaurant and more restaurants and shops. Very clean, private back yard, heated pool, coffee station... really everything you need for a relaxing and enjoyable stay in Sarasota.