Family-friendly vacation rentals in Pinellas County

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Top-rated family-friendly rentals in Pinellas County

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Guest favorite

Guesthouse in Largo

4.99 out of 5 average rating, 301 reviews

Paradise Cottage Largo 2 miles to beach private+

We are PARADISE COTTAGE and the standards of super host are status quo! Come on down - we're ready for you! Although only 2 miles from the Gulf, we're on high ground! We are on a Priority One Energy Grid. With over 300 plants, many trees, we live in a lush tropical "Paradise". Our guests' highest praises include the private, quiet, serene, safe and secluded attributes we're fortunate to claim, no neighbors while being so close to so much. Read on in the next section "The Space" to learn more

Nov 20 – 27

G$29,237 GYD per night

Guest favorite

Condo in Indian Shores

4.96 out of 5 average rating, 112 reviews

"Sunsational" Indian Shores Getaway!

Updated studio perfect for your beach vacation! Great location with the Intercoastal Waterway in your backyard & access to the public beach right across the street in front! When you’re not soaking up the sun & sand, you’ll appreciate the community amenities which include the second largest pool (not heated) on all the barrier islands, boat slips, picnic tables/bbq area, and shuffleboard. The second floor studio is comfortable and equipped with everything you’ll need…just bring your sunscreen!

Jul 13 – 20

G$33,709 GYD per night

Guest favorite

Guesthouse in Saint Petersburg

4.84 out of 5 average rating, 719 reviews

Private & Cozy Tiny Home/Cottage

This is a cozy converted workshop with all the amenities of a traditional home! You'll have a comfy bed that sleeps 2, cable, Netflix, WiFi, air conditioning, W/D, closet space, cooking stuff, & bathroom. If you love tiny homes, you'll love this. Because of it being a converted workshop, it still has that feeling in some regard. It's a little rustic, but still charming. It's not a hotel, nor does it try to be. It's definitely a great place to relax and get a good night's sleep. Pets welcome.

Jan 17 – 24

G$16,143 GYD per night

Guest favorite

Guest suite in Gulfport

4.92 out of 5 average rating, 453 reviews

Gulfport Studio STEPS to Beach & Restaurants

Calling all beach lovers! Fall in love with this unique Gulfport Beach Cottage! Colorful, light & bright. Located on a corner lot STEPS from popular Beach Blvd & Gulfport beach, fishing pier, eclectic Gulfport shops, cafes and everything FUN! Gulfport has artsy and quirky shops, fabulous waterfront restaurants and a thriving art scene. Gulfport is a funky community all its own. Gulfport has an Art Walk on the First Friday and Third Saturday and a Tuesday market every week. Don’t miss it!

Sep 19 – 26

G$25,757 GYD per night

Guest favorite

Apartment in Treasure Island

4.92 out of 5 average rating, 162 reviews

Treasure Island Beach Apartment #1

Location! Situated on Gulf Blvd, directly across from the 123rd Street beach access in Treasure Island. Walk to John's Pass for restaurants, shopping, bars and music, boat trips and fishing. Two bedroom, one bath private apartment, with all the amenities you need for a great beach vacation - beach chairs, umbrella, cooler, barbecue, bicycles. Master bedroom has queen bed, and Roku tv. Smaller bedroom has twin trundle bed, perfect for the kids. Full kitchen. Off street parking for one car.

Mar 18 – 25

G$26,554 GYD per night

Guest favorite

Condo in Tierra Verde

4.96 out of 5 average rating, 237 reviews

Natural Beauty on Tierra Verde, Waterfront Condo

Feels like the Florida Keys! Fully renovated & well appointed second floor, 1 bed, 1 bath condo in Holiday Island condo resort. The condo features a beautiful waterfront & pool view, tennis, bicycles, hot tub, dock with grills, gym, and more. Remodeled in 2015 the condo features a fully equipped kitchen, Keurig coffee maker, beautiful views from the living room, dining room, kitchen, balcony. Walking distance to many local restaurants & minutes away from St. Pete Beach & Fort DeSoto.

Oct 11 – 18

G$27,381 GYD per night

Guest favorite

Guest suite in Largo

4.97 out of 5 average rating, 317 reviews

Private Pool, Jacuzzi, Walk to Beach.

This Guest Suite is a large Studio Apt(360 sq ft) attached to our home. It has a private entrance, a large bath, large bedroom with pool view and private deck. Also includes a kitchenette with full size fridge, toaster, coffee maker and microwave. No Stove. Complimentary breakfast snacks including Coffee and tea. Relax on the deck and watch the birds on the bird feeder or grab our bikes, beach chairs and head to the beach. Grill available. Please read house rules before booking.

Oct 5 – 12

G$24,063 GYD per night

Guest favorite

Condo in Indian Shores

4.96 out of 5 average rating, 143 reviews

1 BR direct beachfront! Now avail. 8/29-9/11.

Our condo is directly on the beach!! It is close to restaurants and dining, mini-golf, Clearwater and St. Pete's Beach. About 25 miles from Tampa, Florida for the Buccaneers NFL football and Lightning NHL hockey! We are about 37 miles from Busch Gardens. Only 95 miles to Disney World in Orlando! Mini-golf right across the street! You’ll love my place because of the neighborhood. My place is good for couples, small families, solo adventurers, and business travelers.

Dec 10 – 17

G$30,623 GYD per night

Guest favorite

Farm stay in Odessa

4.98 out of 5 average rating, 173 reviews

Farm and lake stay at Malfini Cay

PRIVATE GUESTHOUSE...Lakefront -full kitchen living room-very large bedroom-full bath-2.5 acres. Newly decorated/remodeled. 2 flat screen TVs-Roku (Netflix and Spectrum app)-WIFI -laminate flooring-high thread count sheets-comfy queen bed. IKEA sleeper sofa in livingroom. All kitchen appliances with coffee bar/Keurig-W/D. Wooded setting-beautiful views of ski lake. Gas grill/firepit. HOUSEBROKEN PET FRIENDLY. WE NOW CHARGE A PET FEE (see below for details).

Oct 25 – Nov 1

G$30,797 GYD per night

Guest favorite

Apartment in Madeira Beach

4.94 out of 5 average rating, 230 reviews

Madeira Beach and John's Pass #1

Beautiful new rental for your beach enjoyment. Brand new kitchens with granite counter tops and new appliances. Washer and dryers in each unit. Brand new Bathrooms with tiled showers. New tank less water heater. Private back patio with a gas grill for cooking all that fresh seafood from the Gulf of Mexico. Quiet street and walking distance to restaurants, entertainment and bike/kayak rentals and 1 block from beach.

Nov 27 – Dec 4

G$31,749 GYD per night

Guest favorite

Apartment in Redington Shores

4.96 out of 5 average rating, 113 reviews

Beach Avenue #6-Steps from the Beach

Coastal 1 bedroom, 1 bath apartment. Bedroom has a queen size bed, dresser, closet; 1 bathroom; a living area with a full kitchen, queen size sleeper sofa, dinette area. Can offer pack 'n play or air mattress if requested. Steps away from the beautiful white sand beach of Redington Shores. We do allow pets in this Unit as long as they are well behaved and comfortable if left alone.

Sep 26 – Oct 3

G$32,040 GYD per night

Guest favorite

Home in Pinellas Park

4.9 out of 5 average rating, 286 reviews

Lovely Home in Quiet Neighborhood!

This is a lovely home in quiet neighborhood. Beautiful wood laminate flooring, modern feel with wifi, 55" smart tv, Sleep Number queen bed and tv in master bedroom. Quick access to Tampa and St. Pete/Clearwater airports, beaches, nightlife and culture in St. Petersburg and Tampa plus shops, restaurants and malls. Getting around Tampa bay is a cinch from here!

Oct 1 – 8

G$21,142 GYD per night