Holiday rentals in Gulfport
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Top-rated holiday rentals in Gulfport
Guests agree: these stays are highly rated for location, cleanliness and more.
The Pelicans Roost / Gulfport
The Pelicans Roost is a remodeled home, with a new fully stocked kitchen with all your cooking and entertaining needs. All new furnishings, a screened in back porch and a patio with an outside table and grill. The yard is completely fenced and lined with tropical plants and trees for your privacy. This spacious and comfortable home is clean and in a quiet neighborhood just 5 blocks from all that downtown Gulfport has to offer- the Marina,Beach,Restaurants, Shops, Fishing, Galleries and more...!
The Happy House
Welcome to The Happy House, This piece of paradise was the spotlight home for the 2025 Flamingo Tour of homes ! 🦩The stunning property has everything you need for an unforgettable getaway. Discover a breathtaking garden, 2 charming bedrooms, a modern kitchen with eat-in dining, a welcoming living room, a dining room, and a timeless bathroom. Outside, enjoy a backyard paradise, an outdoor shower, griddle, umbrellas, lounging areas, and a quaint beach spot. Your next favorite escape is waiting!
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.
Mockingbird Bungalow min to beaches
This memorable place is anything but ordinary. This is a 1 bedroom 1 bathroom private bungalow with all the amenities you need for the perfect vacation! This property is the perfect cozy beach getaway for 2 people. You'll enjoy your cup of coffee on the enclosed private patio each morning while watching the native butterflies and birds. This tiny bungalow is less than 10 min. to St. Petersburg's beaches and 10 min. to downtown St. Pete. *Please read all additional information with listing*
Stunning Brand New Modern Coastal Home
Coastal luxury meets Gulfport charm in this stunning new construction elevated home - completed in November of 2021. Located in an ideal location in the heart of Gulfport: just four blocks from Gulfport beach park and two blocks from Beach Blvd where you will find Gulfport's many wonderful restaurants and shops. This modern 1,450 square foot home is raised on piers with the entire living area positioned on the second floor and a spacious area below it dedicated to parking and outdoor living.
Cozy Cottage for Lovers
Relax, reconnect and revitalize in this private, intimate cottage that has everything you need to leave the hustle and bustle behind. Surrounded by lush tropical vegetation in the shade of giant live oaks and located in the Gulfport Arts District, you're a short walk or bike ride from excellent urban parks, restaurants, live music, fashion and art boutiques, dancing at the Gulfport Casino, community theater, and a beautiful beach that looks out over sailboats moored in Boca Ciega Bay.
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.
Gulf Guesthouse - king bed, 3 blocks to downtown.
Be our guest! Welcome to our family compound where you will enjoy the treetop views from our second story carriage house guest apartment. You'll be surrounded by the tropical serenity of lush palms and plants, both inside and out, while being just around the corner from the excitement of downtown Gulfport. Our updated one bedroom apartment is fully furnished and stocked with all of the things you'll need for an extra comfortable, enjoyable stay. We look forward to hosting you!
Avocado Casita 10 mins to Beaches
Newly built studio -- small space, smart design. An intimate studio space meant for a minimalist lifestyle complete with full amenities. Compact yet comfortable, it’s the perfect place for a restful sleep in between your daytime adventures. Pack light, live easy. 3 blocks from Stetson Law School 3-4 blocks from the Pinellas Trail ~1.5 miles to Gulfport’s Beach Blvd 3 miles to Award Winning St. Pete Beach 4 miles to Award Winning Treasure Island ~4.5 miles to Downtown St Pete
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!
Modern Chic Beach Home
Providing today’s comfort with yesterday’s charm. Welcome to our lovely Airbnb house in the heart of vibrant Gulfport! This is the perfect vacation home for beach and shopping lovers, as it's just a short stroll away from the beach, downtown shops, and tennis court. You'll fall in love with our quiet and peaceful neighborhood, which offers the perfect balance of relaxation and fun. So come stay with us and experience the best of Gulfport living!
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
Popular amenities for Gulfport holiday rentals
Other great holiday rentals in Gulfport
Salty Air Retreat 10 minutes to St Pete Beach
Downtown Gulfport/Heated Private Pool
Sunshine State of Mind
The Beach Way Garden Villa - Walk to Everything!
Flamingo Corner
*POOL* Fenced Yard *Shuffleboard Court*
Lovely rental Unit one block from the beach
Beautiful Boca Marina Apartment
When is the best time to visit Gulfport?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £101 | £114 | £123 | £106 | £96 | £92 | £92 | £91 | £89 | £92 | £89 | £97 |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°C |
Frequently Asked Questions
What are the best places to stay in Gulfport?
Many travelers seek vacation rentals in Gulfport’s waterfront district or close to the downtown area, where you find walkable access to shops, beaches, and eateries. Houseboats, cottages, and bungalows are often requested for unique stays.
What are the best things to do in Gulfport with kids?
Enjoy playgrounds and gentle waves at Gulfport Beach Park, explore the small shops for treats, or stop at community art events and outdoor concerts. Family-friendly markets are active with crafts, face painting, and snacks.
What are some of the best things to do in Gulfport?
Stroll the colorful waterfront district, browse local galleries, or relax at Gulfport Beach Park. Many visitors enjoy live music, open-air markets, and fresh seafood at locally rooted restaurants around the town center.
How is the weather in Gulfport?
Gulfport is known for warm, humid summers near 91°F (33°C) and milder winters around 53–74°F (12–23°C). Rain is more frequent from June to September, so consider packing a light rain jacket if visiting during these months.
When is the best time to visit Gulfport?
Milder temperatures and lower humidity in late fall and early spring are often recommended, especially for outdoor activities. Seasonal festivals and neighborhood events bring extra energy during these periods.
What are the best places to visit in Gulfport?
Gulfport has a walkable historic downtown with shops, art galleries, and murals. The Gulfport Tuesday Fresh Market is frequently suggested for local produce and crafts, while Gulfport Beach Park is a popular spot for picnics and sunset views.
What are some hiking trails in Gulfport?
Gulfport Beach Park has an easy, waterfront walking trail with palm trees and picnic spots. For a nature walk, look for nearby preserves with boardwalks through wetlands and shaded paths lined with native plants.
What are some family activities we can do in Gulfport?
Families can play at Gulfport Beach Park, visit weekly farmers markets, or attend outdoor movie nights and festivals in the historic downtown area. Sidewalk cafés and pizza spots make it easy to enjoy meals together near the waterfront.
What are some of the best day trip ideas from Gulfport?
Explore the vibrant art scene and waterfront parks in downtown St. Petersburg, stroll the sandy shores of Treasure Island, or discover the historic boutiques and seafood spots around Pass-a-Grille Beach. Areas known for natural preserves and coastal trails are also often suggested nearby.
Are there any pet friendly accommodations available in Gulfport?
Many vacation rentals and cottages in Gulfport welcome pets, especially near the waterfront district and green spaces. Some hosts provide fenced yards or easy access to parks for walks with your dog.
What are some local tips for visiting Gulfport?
Try visiting markets and galleries early in the day for fewer crowds, and explore side streets for colorful murals and neighborhood gardens. Locals often suggest checking community calendars for live music, art walks, and food events during your stay.
What is Gulfport known for?
Gulfport is known for its inclusive arts community, live music scene, and colorful historic district filled with local galleries. The town has regular markets, diverse eateries, and a distinct, welcoming atmosphere that draws visitors year-round.
What are the best hidden gems to explore in Gulfport?
Look for vibrant mosaic art installations tucked along side streets, small neighborhood parks, and locally owned coffee shops with live music nights. The historic waterfront district holds independent galleries showcasing local artists and craft makers.
What are the best foods to try in Gulfport?
Gulfport is known for fresh Gulf seafood like grouper sandwiches, crab cakes, and locally inspired tacos, along with favorites from bakeries and casual waterfront cafes. Many restaurants serve vegetarian, vegan, and gluten-free options reflecting the town’s diverse tastes.
What should I bring for a trip to Gulfport?
Pack light clothing, comfortable shoes for walking, and swimwear for the beach. Sun protection like hats and sunscreen is recommended, as well as a reusable water bottle for staying hydrated.
What is the nightlife in Gulfport like?
The nightlife in Gulfport is relaxed, with local bars, laid-back pubs, and venues featuring live jazz and acoustic sets. Visitors enjoy small stages for open mic nights or catching local bands in the historic waterfront area.
What are the most popular events or festivals in Gulfport?
The Gulfport Tuesday Fresh Market is held year-round and highlights local vendors and artisans. Seasonal art walks, waterfront festivals, and themed parades around holidays are also frequently suggested for visitors seeking community events.
Are there family friendly vacation rentals in Gulfport?
Gulfport has many family-friendly vacation rentals, including homes and cottages near the waterfront and parks. Choose neighborhoods around the town center for easy access to beaches, playgrounds, and casual dining.
Quick stats about holiday rentals in Gulfport
Total holiday rentals
Explore 450 holiday rentals in Gulfport
Nightly prices starting at
Gulfport holiday rentals start at £7 per night before taxes and fees
Verified guest reviews
Over 19,570 verified reviews to help you choose
Family-friendly holiday rentals
270 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 210 rentals that welcome pets
Holiday rentals with a pool
130 properties feature pools
Rentals with dedicated workspaces
240 properties have a dedicated workspace
Wifi availability
440 of Gulfport holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Gulfport rentals
4.8 Average rating
Gulfport stays are highly rated by guests – averaging 4.8 out of 5!
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