Family-friendly holiday rentals in Gulfport

The Flamingo Flat

This is a charming freshly painted mid-century modern "Old Florida Coastal" home! Great location with off-street parking. Fully furnished covered porch with ceiling fans in very private partially fenced yard. Just a 1 mile walk or ride to Gulfport Beach and Arts District, and 3 miles to Sunset Beach on the pristine Gulf of Mexico. Two bedrooms (1 queen and 1 twin). People of ALL sizes, colors, beliefs, cultures, religions, sexes and backgrounds are welcome here as long they DO NOT SMOKE!

Shady Paradise Close to All!

Totally remodeled 1960's bungalow with retro old Florida furnishings, two bedrooms with comfy new mattresses on 3 beds, and a foldout bed to sleep extra guests. Comes equipped with everything you need for a great vacation! Full kitchen, dining area, and private yard with mature trees. Free laundry facilities on site. Perfect for families- and pets are welcome too! Parrot Park is a shady and quiet vacation retreat, located a short walk from restaurants, nightlife and Gulfport beach!

Cozy Dream FL Vacation Home Pool is heated!

We invite you to gather in our updated, beautiful ranch style home with a pool, fenced backyard, and beautiful new patio. We have high standards for cleaning and sanitizing between guests. We take great care to keep your family safe. Centrally located, it is ready for Eckerd College families, or your kid-friendly family vacation! Minutes away from beaches, golf, trails, downtown, & Tampa with easy access from I-275. Let us know when you will be visiting the area!

The Lassing House

A very beachy, cozy and charming detached house with private access and parking. It is fully furnished with a fold out couch memory foam mattress and open bedroom with queen bed. One block from beautiful Lassing Park on Tampa Bay. Gorgeous sunsets, amazing museums, restaurants, concerts, breweries and beaches are just minutes away! Equipped with a mini split AC, the apartment stays cool and quiet. Note that the cottage is equipped with a stove but no oven.

Charming apartment in Historic Kenwood

Cute, spacious apartment located in Historic Kenwood, which was named 2020 “Neighborhood of the year” by NUSA. Our apartment is above our large garage. Lots of charm and just enough space to spread out a little for some privacy. Located close to downtown, walking distance to lots of restaurants, breweries and bars but still a short drive to our beautiful beaches. You access the apartment through our side gate and up an exterior stairway.

Gulfport Beach Studio on Bay

This rustic studio- 'the annex'- can be rented with Waterfront 1BR-Private Beach (https://www.airbnb.com/rooms/10678164) or 2BR Private Beach Paradise (https://www.airbnb.com/rooms/2459284) as an additional space on the same property. It is steps to restaurants, nightlife, public transport, the beach, and family-friendly activities. You’ll love my place because of the retreat-like feel, the light, the comfy bed, and the neighborhood.

Casa O - Private In-Suite Studio in St. Pete

Enjoy this NEW cozy studio, located in Crescent Heights neighborhood, 7 min from downtown St. Pete. Perfect location to walk to Trader Joe's, Fresh Market, Crescent Lake, Trips and much more. The studio has 2 twin size beds and one more trundle bed that you can pull out, a sitting area, a private bath and a perfect farm decor kitchen. It has its own entrance from the street so you would have complete independence.

Fresh & Friendly in Marina District Private Oasis

Bright, clean, and thoughtfully appointed, Harbor Mist brings new meaning to home-away-from-home. This Gulfport gem is tucked in one of the town’s friendliest neighborhoods - home to smiling locals who gather and relax at the marina just down the street. Bring your pup along and you’re both guaranteed to make new friends. Or re-connect with your loved ones in the comfort of laid-back living spaces.

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!