House holiday rentals in Gulfport

Tropical Disco|Luxury|Top 5%|Pool|Mins to Beach

There's even a disco ball! 🪩Perfect for Bachelorette & Bachelor get aways, Retreats, and Family Vacations! Gather in the spacious living room to watch movies on the 65-inch smart TV or prepare a feast in the well-equipped kitchen, complete with brand-new appliances. After a day of fun in the sun at St. Pete Beach, relax in your private bedroom with comfortable beds, soft linens, and modern decor. Wake up to beautiful natural light and enjoy a cup of coffee on the patio overlooking the pool.

The Driftwood - Pet Friendly

Welcome to The Driftwood's nautical retreat. This cozy 2-bedroom home is a haven of maritime-inspired style, offering a unique and refreshing escape for your stay. Unwind in your private yard with a fire or dinner at the outdoor dining area. Have your pet staying with you? They are welcome here! This beautiful diverse neighborhood is one mile away from Gulfport's beach blvd. where you can shop, dine, or stroll the beach. 6 miles away will take you to the famous St Pete Beach or St Pete Pier.

Barefoot Parrot /Walk DT & Waterfront/Sleeps 8

Steps from Main Street Dunedin, a short walk to the waterfront and an easy drive to award-winning beaches, Honeymoon Island & Clearwater Beach. Experience the charm of the Barefoot Parrot House, a private pet friendly house with designer decor and abundant outdoor space. Walk, bike, or cart to stunning sunsets, shops, dining, breweries, and Pinellas Trail. Great for families, couples, groups. Loaded with beach gear, kids's items & pup supplies. Treat yourself to this beloved Dunedin favorite!

Central location - mins to Downtown and Beaches

☀️Rest assured, you’ll wake up close to all the excitement St. Petersburg has to offer! Perfect for solo travelers, couples, or small groups of friends and family, this cozy home is centrally located between downtown and the beaches, offering the ideal balance of fun and relaxation. 🚗 Quick Drive Times: • 8 min – Downtown St. Pete & The Pier • 12 min – St. Pete Beach • 25 min – Clearwater Beach • 25 min – Tampa & Airport Experience the best of St. Petersburg—scroll down to learn more!🌊

Gecko House Unit #1

Romantic little apartment which is the lower left half of the house next to Downtown Gulfport. Here you will find many shops, restaurants, and even a dancing hall a short walk away. Enjoy live bands during the day and Karaoke at night at some of the greatest bars in Florida. Not to mention, one of the best beaches is right next door. It even contains beach volleyball nets for daily use. Take a stroll down to the pier and enjoy the sites of the marina, or enjoy a beautiful sunset at night.

Hibernate in our Bear Creek Home

This 3 bedroom 2 bath home is located in beautiful Bear Creek. Don't worry, no bears! Great place to relax and enjoy the pool, in a quiet, safe neighborhood. Next to Pinellas Trail, a 40 mile paved trail. Great for walking, running and biking. You can bike downtown 6 mi or 4.6 miles to beaches. We have bikes and for those more adventuresome we have kayaks you may use. House features stable, high speed internet. Close to great restaurants, drugstores, supermarkets and coffee shops.

1920s Cottage, 2BR/2BA, Walk to Beach & Art Walks

Tucked on a quiet brick-lined street in the heart of Gulfport’s historic waterfront arts district, this enchanting 1920s cottage is the real Florida — sun-drenched, unhurried, and full of character. Walk six blocks to the beach, four blocks to waterfront dining, and step outside on Tuesday mornings for the beloved Fresh Market. On First Fridays, the neighborhood comes alive with Art Walks, live music, and local makers. This is the kind of place people come back to every year.

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.

Little gem in South Pasadena

Relax with the whole family in this 2 bedroom 1 bathroom, and one game room house. Free parking in front of the house. Washer and dryer available to use. A little covered patio in the back yard, and an outside grill for those fun nights. Large tv in the living room, and a smaller one (40inch) in the “kids” room. Dedicated work table. There is a mini foosball table that converts to air hockey, mini ping pong, mini pool table and more games, in case you get stuck inside.

Peaceful Getaway Close to Amazing Beaches!

This property is nestled in a quiet neighborhood just a mile from the beautiful Gulfport Waterfront District. It’s the perfect place to get away and relax or work remotely! You’ll be in the front unit of a duplex, minutes away from our awesome town of Gulfport, renowned beaches on the Gulf, gorgeous local parks and preserves, lots of artsy shopping spots, and dining options for every palette! This sanctuary is furnished with everything you might need!

Blush by the Bay Gulfport | Walk to Waterfront

Blush by the Bay | Gulfport's luxury coastal escape for groups up to 10. This stunning 3-story waterfront home features 3 king suites with private balconies, bay views, and en-suite baths. Watch boats glide by from one of 3 furnished balconies or unwind at the custom wet bar. Full kitchen with premium appliances, open dining, and smart TVs throughout. Steps to beach, marina, Tuesday Market, and restaurants. Your perfect Gulf Coast retreat awaits.

The Boho | Walk to Gulfport Beach & Restaurants

Boho inspired cottage in the heart of the Gulfport Waterfront District. Steps away from Gulfport beach, restaurants, and nightlife. Enjoy strolling along Beach Boulevard where you'll find local coffee shops, ice cream parlors, Gulfport brewery, and eclectic shops. Relax in the comfort of your backyard oasis or enjoy some fun in the sun with the best Gulfport has to offer right outside your back door.