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!

Adorable Cottage, Pet friendly, near beach & DT

The Cottage is a beautiful, comfy, clean, peaceful home where you will feel just at home, in the hearth of St Pete. It is in a great location, safe & quiet neighborhood, easy-to-access, just a short drive or bike ride away (5-10 minutes) to many good restaurants, grocery stores, museums, library, coffee place, breweries, hospitals, bars and night clubs in downtown & sandy white beaches. Jumped in the sun runner or public transport to downtown or beaches. Perfect for long stay.

Gulfport Art District - One Block From Beach!

Welcome to Uncle Finley's! Situated in the heart of Gulfport's Art and Waterfront District, This cottage listing is for unit A of the duplex. Step outside and walk to Gulfport Beach only one short block away, experience the highly-rated restaurants and shops, or browse local arts and crafts during the weekly Tuesday Morning Market during your stay. Want to experience more of Tampa Bay? Downtown St. Pete, St. Pete Beach, and I-275 access are only ten minutes away.

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!