Family-friendly holiday rentals in Gulfport

Adorable Suite: 15min to beach, 10min downtown

Entire apartment with a complete kitchen, full bath, A/C, WiFi (300mbps), you have a private entrance and all the comforts of home. Comfortable queen size bed. You are located 15 minutes from St Pete Beach and 10 minutes to downtown St Pete. You have off street parking. Very safe and quiet location. You have an easy check in via lock box after 3pm, and check out is simple, leave the key then lock the door behind you. We have plenty of secret spots to recommend. Very experienced Super Hosts.

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!

Pool home with beach a few minutes away

This recently updated European style home comes with 3 bedrooms 2 bathrooms, screened-in pool and pool deck. Located in an upscale neighborhood, this beautiful home offers patio areas and large living room for relaxing. Equipped with a full size washer, dryer and full kitchen for a home away from home experience. 5min drive to beaches, parks, lakes, trails, shopping & restaurants. 10min to downtown, St. Pete. Boat Trailer parking available. Large driveway can accommodate up to 3 vehicles.

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

My place is across the street from Target and many restaurants within walking distance. There is a PSTA Bus stop right at the entrance to the condo property.Uner and Lyft are availablThe Pinellas Trail is across the street. The VA Hospital and Bay Pines Park are biking or walking distance. The closest beach is Madeira Beach 2 miles from the condo. All Utilities, Cable/Internet are included. Parking is free and close to the elevators. Plenty of parking spaces are available also.

Kenwood Oasis

Message for open dates not on calendar. Spanish Mediterranean style with rustic charm and modern amenities compliment this homes beautiful exposed brick and stained glass doors. The outdoor living space is amazing with a screened in 30’x30’ breezeway for perfect FL living. Lush tropical landscaping, a great yard and tons of parking on a completely fenced in 1/2 acre lot and all the privacy guests could ask for. Located just 5 minute drive to Central Ave. Downtown St. Pete.

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.

Lovely Guesthouse

We are ideally situated close to Tampa, Sarasota,Clearwater and St. Petersburg. Our neighborhood is wonderful, eclectic, alive. We have incredible restaurants a walk away. Our beach is walking distance. If you prefer you never have to leave Gulfport from the day you arrive. Everything you want is right here. There is free access for charging your electric vehicle on the beach in town which is walking distance from our guesthouse

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.

Elegant & Relaxing Beachside Paradise - Pool

Hurricane Update!! This condo is currently undergoing a full renovation due to some storm damage, with a projected reopening date of July 15th. It will be refreshed and better than ever—stay tuned! The grounds have been completed, with some first-floor renovations still ongoing in the community, and the pool is open and heated!!