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Gulfport, FL Vacation Rentals

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Our Favorite Vacation Rentals in Gulfport

  • Beautiful Pool View | Steps from White Sand Beaches
     Home/Apartment
    RedAwning
    From
    $412
  • Comfy & Stylish Getaway
     Family Stay
    Booking.com
    From
    $79
  • Resort Style Living
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $497
  • Vistas On The Gulf 506
     2br Home/Apartment
    RedAwning
    From
    $831
  • Coastal Comfort 1br w/ Pool - Near Bay + Dining
     Home/Apartment
    Booking.com
    From
    $219
  • Room for rent in St. Petersburg
     Home/Apartment
    HolidayLettings
    From
    $45
  • Sunset Beach Chateau Treasure Island 8470
     Home/Apartment
    RedAwning
    From
    $572
  • Whispers Resort #6 DLX 1B/R Condo
     Home/Apartment
    Booking.com
    From
    $243
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Check prices for these upcoming dates

Gulfport Vacation Rentals with a Pool

  • Pass-A-Grille Boutique/Anheiser Busch Resort
     10br Home/Apartment
    RedAwning
    From
    $4,799
  • Country Inn & Suites by Radisson, St. Petersburg - Clearwater, FL
    Nice70br 3-star Home/Apartment
    Booking.com
    From
    $154
  • Arie Dam 403
     2br Home/Apartment
    RedAwning
    From
    $2,195
  • Sunny Updated Beach Condo w/ Resort-Style Pool
     2br Home/Apartment
    RedAwning
    From
    $494
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Gulfport Vacation Rentals with Wi-Fi

  • Beach Haven B4
     3br Home/Apartment
    RedAwning
    From
    $1,856
  • Northeast St Petersburg 1950's Cottage 3701
     2br Home/Apartment
    RedAwning
    From
    $371
  • Pass-A-Grille Anheiser Busch Resort Bay&Boat
     8br Home/Apartment
    RedAwning
    From
    $3,232
  • Pass-A-Grille Anheiser Busch Resort Bay House
     6br Home/Apartment
    RedAwning
    From
    $1,684
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Gulfport Pet-Friendly Vacation Rentals

  • Tropical Fruit Garden,Heated Pool,Hot tub. about 5 minute drive to the beaches.
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $408
  • The Quiet Little Coconut
     Home/Apartment
    Airbnb
    From
    $130
  • The Vintage Jungle Bungalow
    Excellent2br Home/Apartment
    Airbnb
    From
    $181
  • Oceana 2 Bedroom/2 Bathroom Bay Front Suite
    Excellent2br Home/Apartment
    Airbnb
    From
    $561
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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.

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Price and Availability in Gulfport

Most expensive
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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.
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The Weather in Gulfport

Rainy days
81° 45°
4
84° 52°
2
83° 48°
1
87° 58°
1
91° 68°
3
94° 73°
4
95° 73°
13
94° 73°
12
96° 75°
1
91° 71°
7
88° 52°
0
82° 48°
5
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Rainy days

This climate histogram shows you the weather patterns in Gulfport. The hottest month in Gulfport is April, when temperatures peak at 96 ˚F. The coolest month is December, when temperatures drop to 45 ˚F. The wettest month in Gulfport is June with 13.48 inches of rain, while the driest month is February with 0.47 inches of rain.

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What Expert Travelers Think

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    Jeff Campbell
    Jeff CampbellMiddle Class Dad
    Middle Class Dad

  • — I love AllTheRooms because it enables me to compare a range of providers in just one search. I'd normally spend time checking prices across a range of platforms by visiting different websites one-by-one, so this helps me to save time on my accommodation searches while planning my upcoming trips

    Kacie Morgan
    Kacie MorganThe Rare Welsh Bit
    The Rare Welsh Bit

  • — 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
    Kid World Citizen

Vacation Rentals in Gulfport

At AllTheRooms.com we have accommodations from all of the best providers - Airbnb, Priceline, RedAwning and others. We have 604 vacation rentals, hotels and other places to stay in Gulfport ranging from budget options to extravagant places to stay. For those wanting to save money, the cheapest place to stay in Gulfport is only $25 per night. A typical vacation rental in Gulfport costs on average $233 a night.

Those needing to get some work done during their trip to Gulfport can choose from 289 places to stay that provide WiFi. 38 of our accommodations come with breakfast in the price. You can maintain your workout routine by staying at one of 18 accommodations that provide gym facilities. If you are driving to Gulfport, you'll want to pick from 285 places to stay that provide parking. We track 45 accommodations that have a pool or jacuzzi.

If you're traveling with a furry friend, then make sure to choose one of the 139 pet-friendly accommodations available.

In Gulfport AllTheRooms currently compares hotels, vacation rentals, hostels from more than 3 providers, including 289 places to stay from Airbnb, 4 accommodations from Priceline and 4 places to stay from RedAwning.

428 accommodations in Gulfport have been reviewed; 73% are rated highly. 248 places to stay in are instantly bookable.

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