Gulfport, FL Vacation Rentals

Our Favorite Vacation Rentals in Gulfport

  • Pelican Place Two
     Home/Apartment
    Booking.com
    From
    $125
  • Luxurious and Cozy Bungalow
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $430
  • Beach House Suites By The Don Cesar
     Home/Apartment
    NextTrip
    From
    $395
  • holiday home for max. 6 persons in St. Pete Beach , Florida, Florida
     Country House
    TUIvillas
    From
    $166
  • Close to Beach/Host Guide
     Family Stay
    Booking.com
    From
    $90
  • Private room in elegant 2/2 condo, 920 sf., 3 mi. to St. Pete Beach!
    GoodHome/Apartment
    HolidayLettings
    From
    $48
  • Residence Inn St Petersburg Treasure Island
     Home/Apartment
    NextTrip
    From
    $366
  • Gulf Strand Resort 308 Condo
     Home/Apartment
    Booking.com
    From
    $190

Check prices for these upcoming dates

Gulfport Vacation Rentals with a Pool

  • Country Inn & Suites by Radisson, St. Petersburg - Clearwater, FL
    Nice70br 3-star Home/Apartment
    Booking.com
    From
    $86
  • Hibiscus Hideaway Private Oasis
    ExcellentHome/Apartment
    Airbnb
    From
    $101
  • Solar powered house with heated pool and game room
    Excellent2br Home/Apartment
    Airbnb
    From
    $189
  • Cute 1950's bungalow in central Saint Petersburg!!
    ExcellentHome/Apartment
    Airbnb
    From
    $74

Gulfport Vacation Rentals with Wi-Fi

  • Gulfport Guest Suite!
    Excellent2br Home/Apartment
    Airbnb
    From
    $85
  • 🍾Renovated Modern Efficiency in Old Town Gulfport
    ExcellentHome/Apartment
    Airbnb
    From
    $120
  • Gulfports' Hidden Bungalow
    Excellent2br Home/Apartment
    Airbnb
    From
    $167
  • Gulfport Artist's Garden Escape
    Good2br Home/Apartment
    Airbnb
    From
    $212

Gulfport Pet-Friendly Vacation Rentals

  • Pass-A-Grille Beach House
    ExcellentHome/Apartment
    Flipkey
    From
    $261
  • Tropical Fruit Garden,Heated Pool,Hot tub. about 5 minute drive to the beaches.
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $249
  • Misty Isles Redington Beachfront Unit 5
     Home/Apartment
    HolidayLettings
    From
    $402
  • Special $155/Night!
     5br Home/Apartment
    HolidayLettings
    From
    $1,090

Gulfport Travel Guide

Gulfport is a charming seaside city in Pinellas County, Florida. Over the years, the city has become known for its spunky attitude and zest for life, as well as its locally owned one-of-a-kind stores, restaurants, and “no chain stores” motto. Here, visitors can experience authentic small town Florida.

Things to Do in Gulfport

One of the first things that many visitors do upon arrival to Gulfport is make their way to the beautiful Clam Bayou Nature Park, which features a number of easy walking trails and wooden decks to go out over the bayou for special moments and spectacular bird watching.

Visitors can also experience Gulfport’s beauty by zip lining in Caldwell Park, duck and blue heron watching in Ted Phillips Wood Ibis Park. Alternatively, enjoy beach volleyball at Gulfport Municipal Beach and then cross the street into downtown Gulfport and hit a classy bar, or embark on a shopping adventure.

Visitors who like to hike can take a walk up the Devil’s Shade Trail, taking in the views of whales in the distance, and those who want to purchase some unique art or trinkets can visit Beach Boulevard and make their way into one of the many art and novelty shops. Little Tommie’s Tiki is a popular spot on the boulevard, offering 21+ entertainment, craft beer, and performances every week.

Best Places to Stay in Gulfport

Within the Gulfport/St. Petersburg area, there are dozens of available vacation rentals. Some of the rentals are located on the beach, while others are tucked into the crowded city streets and directly in the middle of all of the excitement. Each rental is kept tidy and up to date, and has its own personality which shines through thanks to the modern decor found inside of each home.

Best Time to Visit Gulfport

The best time to visit Gulfport is from February to May when the weather is pleasant and great for exploring outdoors.

Best Events in Gulfport

One of the best events to take place in Gulfport each year is GeckoFest -- a large celebratory parade that offers costume contests, street performers, live music, and over 150 arts, crafts, and food vendors.

Another fun event is the Annual Arbor Day celebration, which honors Arbor Day by way of refreshments and the handing out of free sweetgum and red maple seedlings. A few more great events include the Holiday Hoopla, Shipwrecked Music Festival and International Cuban Sandwich Festival in nearby Tampa, and the 4th of July celebration.

Things to Do for Families in Gulfport

The Gulfport Tuesday Market is a great place for families to purchase fresh produce and health items, selling everything from vegetables to all-natural vitamins and health supplements, and providing hours of shop-till-you-drop fun.

Price and Availability in Gulfport

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The cheapest day to stay at a vacation rental in Gulfport tends to be Monday, while the most expensive day tends to be Saturday. Vacation homes in Gulfport tend to be busiest on Fridays, while it tends to be much quieter on Tuesdays.
The most expensive month to stay in a vacation rental in Gulfport is in March, while the cheapest month is in May. The most popular time to book a vacation rental in Gulfport is in the high season in March. Gulfport has its low season in September, when less people are visiting and the vacation home occupancy rate drops.

The Weather in Gulfport

Rainy days
87° 49°
1
82° 49°
6
78° 32°
3
85° 56°
1
83° 53°
1
87° 60°
1
92° 70°
10
94° 74°
7
93° 64°
5
94° 73°
8
93° 73°
4
92° 63°
1
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Rainy days

This climate histogram shows you the weather patterns in Gulfport. The warmest months in Gulfport are July and May, when temperatures reach 94 ˚F. The coolest month is December, when temperatures drop to 32 ˚F. The wettest month in Gulfport is August with 9.68 inches of rain, while the driest month is November with 0.53 inches of rain.

What Expert Travelers Think

  • — I travel to Boston regularly and I like to use AllTheRooms as it’s tricky to find good accommodation at a good price. The platform is easy to use and provides a complete set of features that saves me time and money on every trip

    Clwyd Probert
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  • — Whenever I am making travel plans I always use comparison sites to find the best accommodation for us at the best price. Whether it be for hotel stays or private rentals AllTheRooms makes this so much easier and quicker as it brings all my searches into one place, with a great offering of options

    Sarah Pool
    Sarah PoolTammymum
  • — As a mom of 5 kids who enjoy traveling, I love AllTheRooms! It is quick and easy to find the best deal on lodging that fits our family, in the area we'd like. AllTheRooms really does save you time, money, and hassle.

    Becky
    BeckyKid World Citizen

Vacation Rentals in Gulfport

Choose the perfect rental for your trip at AllTheRooms.com. We compare Airbnb, RedAwning, Priceline and many more. AllTheRooms has 625 rentals, hotels and other great places to stay while you enjoy Gulfport, with everything from cheap hostels and homestays to luxury Airbnbs and hotels. For those traveling on a budget, the most economical place to stay in Gulfport is available at $9 per night. An average rental in Gulfport costs on average $238 per night.

Those needing to get some work done during their trip to Gulfport can pick from 294 places to stay that include WiFi. 46 of our accommodations come with breakfast in the price. Choose from 16 places to stay that provide gym options, so you don't miss a single workout. If you're planning on getting to Gulfport by car, be sure to choose from 295 accommodations that provide parking. We track 43 accommodations that have a pool or jacuzzi.

Those traveling with a cat, dog or some other animal can stay in one of 141 accommodations that are designated as pet-friendly.

431 of our accommodations in Gulfport have been reviewed and rated. 75% are rated excellent or good. 252 accommodations allow instant booking.

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