Gulfport Holidays
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- Better togetherSave up to S$1,300 when you book a flight and hotel together*
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Gulfport Beach Holiday
Listen to the waves lapping at the shore and stroll by the glistening waters on your Gulfport holiday. If you just need to get away, a trip to Gulfport is just what the doctor ordered. We have a great range of Gulfport holiday deals to select from. Snap one up near Gulfport Beach, just 2 kilometres from the city centre, and live out your holiday fantasies without hurting your budget.
Top hotels in Gulfport
Wyndham Grand Clearwater Beach
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
S$328
30 Aug - 31 Aug
includes taxes & fees
The Westin Tampa Bay
7627 W Courtney Campbell Cswy Tampa FL
Fully refundableReserve now, pay when you stay
S$211
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (1,524 reviews)
"I’ve stayed at a different Westin before so I know the hotel would be amazing. The staff at check in was so helpful, and everyone from the cleaning staff, wait staff, and in between were fantastic. I actually cried when I got in my car to leave because I had the best time."
Reviewed on 26 Aug, 2026
Hilton Clearwater Beach Resort & Spa
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
S$284
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very good! (2,954 reviews)
"Very little beach view even though we paid for one."
Reviewed on 27 Aug, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Stay near popular Gulfport attractions
Gulfport Beach
9.0/10 (21 reviews)
This tranquil waterfront along Boca Ciega Bay offers a peaceful alternative to Florida's busier beaches. Extend your visit with a stroll down Williams Pier or explore the vibrant local arts scene nearby.
Gulfport Casino
This historic 1935 ballroom enchants with its Art Deco charm and 5,000-square-foot maple dance floor. Join nightly Swing, Latin, and Ballroom events or sip cocktails on the bayside verandah.
Gulfport Tuesday Fresh Market
8.6/10 (4 reviews)
This vibrant open-air market showcases local produce, artisan crafts, and live music every Tuesday. Browse stalls of fresh organic vegetables, handmade goods, and local honey while enjoying the community atmosphere.
Island Community Theatre
6.0/10 (1 review)
You can make plans for a show at Island Community Theatre during your stay in Gulfport. Stroll along the beautiful beaches in this family-friendly area or visit its lively bars.
What to do in Gulfport
Sunset Celebration Cruise on Tropics Boat Tours
S$48
per adult
94% of travellers recommend
Guaranteed Dolphin Sighting Tour on Tropics Boat Tours
S$48
per adult
90% of travellers recommend
Clearwater Beach: Dolphin & Island Sandbar Cruise
S$36
per adult
92% of travellers recommend
Frequently asked questions
How much does a Gulfport holiday package cost?
You'll find cheap prices on Expedia for your Gulfport escape. However, a range of factors like the hotel choice, length of stay and season will determine how much your holiday to Gulfport costs.
What are the cheapest months to go to Gulfport?
If you'd like to snag a cheap Gulfport holiday package, consider travelling in September, October and November. You'll generally find better prices on flights and accommodation during these quieter months — ideal for a budget-friendly getaway.
How many days is enough for Gulfport?
Gulfport holidays come in various shapes and sizes, but to get a real feel for this destination, we'd suggest 3 days is a good ballpark. With this timeframe, you can fit in top sights like Gulfport Beach and Gulfport Tuesday Fresh Market and track down some underrated gems. Don't skip neighbourhoods such as Downtown St. Petersburg and United Central either. If you're smart with your time, you can even schedule a day trip or two from Gulfport too.
Is it worth booking a holiday package to Gulfport?
During your Gulfport holiday, you can count on experiencing some excellent culture and dining. Leave enough room in your schedule to visit major attractions like Gulfport Beach and Gulfport Tuesday Fresh Market.
How to find the best Gulfport package deals?
Start your search for a Gulfport package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Gulfport package deal right away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Gulfport adventure underway.
Is it cheaper to book a Gulfport holiday as a package?
You can enjoy significant savings on your next Gulfport break by booking a tailored holiday package. Click on the "Package" heading, then enter your destination and travel dates to view some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Gulfport?
If you have your Gulfport travel dates locked in, book as soon as you can to snap up some terrific deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Gulfport?
- Choose when to go: Check your calendar and get your bags packed. Your favourite season and the type of activities on offer will also help you decide when to holiday in Gulfport.
- Set a budget: Factor in costs such as flights, transportation and food when calculating how much to set aside for your trip to Gulfport. Then, pick a property that suits your budget, whether that's a low-cost stay or a swankier getaway.
- Decide how long to go away for: Now that you're more familiar with Gulfport, you can work out the perfect length of your holiday. Pull together a draft itinerary and give yourself enough time to cover everything you want to see.
- Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised Gulfport holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
