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Gulfport, FL Vacation Rentals

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Our Favorite Vacation Rentals in Gulfport

  • 2BR Gulfport Beach Bungalow
     2br Home/Apartment
    RedAwning
    From
    $327
  • 2nd Avenue S
     Country House
    Booking.com
    From
    $90
  • House Chispa
     2br Home/Apartment
    HolidayLettings
    From
    $290
  • holiday home for max. 6 persons in St. Pete Beach , Florida, Florida
    OkayCountry House
    TUIvillas
    From
    $166
  • Deluxe, Bright, Spacious | Getaway on the Beach!
     Home/Apartment
    RedAwning
    From
    $351
  • Bella Sirena Inn
    GoodHome/Apartment
    Booking.com
    From
    $72
  • GULF FRONT Studio at Beach Resort w/ Pool Tennis Spa Hot Tub & Family Activities
     Studio
    HolidayLettings
    From
    $203
  • Caprice Resort 102
     2br Home/Apartment
    RedAwning
    From
    $294
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Check prices for these upcoming dates

Gulfport Vacation Rentals with a Pool

  • Beachside Bliss w/ Pool - Walk to Restaurants!
     Home/Apartment
    RedAwning
    From
    $292
  • Pass-A-Grille Anheiser Busch Resort Bay&Boat By Tech Travel
     8br Home/Apartment
    RedAwning
    From
    $2,606
  • 2BR Penthouse w/ Panoramic Views
     2br Home/Apartment
    RedAwning
    From
    $393
  • Historic Pass-A-Grille Beach Club Gulf Way 701-5 By Tech Travel
     2br Home/Apartment
    RedAwning
    From
    $444
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Gulfport Vacation Rentals with Wi-Fi

  • Historic Pass-A-Grille Beach Bungalow 3110 By Tech Travel
     2br Home/Apartment
    RedAwning
    From
    $404
  • Northeast St Petersburg 1950's Cottage 3701 By Tech Travel
     2br Home/Apartment
    RedAwning
    From
    $322
  • Pass-A-Grille St Pete Beach Bungalow 105-1 By Tech Travel
     2br Home/Apartment
    RedAwning
    From
    $381
  • Holiday Island 2BR w/ Pool, Hot Tub, Tennis & Dock
     2br Home/Apartment
    RedAwning
    From
    $328
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Gulfport Pet-Friendly Vacation Rentals

  • Renovated St. Petersburg Home -10 Minutes to Beach
    Excellent2br Home/Apartment
    HolidayLettings
    From
    $228
  • NEW! St. Petersburg Apartment, Walk to Vinoy Park!
     2br Home/Apartment
    HolidayLettings
    From
    $225
  • Lovely 3/2 House with pool,hot tub. Only about 5 minute drive to the beaches.
    Excellent3br Home/Apartment
    HolidayLettings
    From
    $249
  • Special $199/Night!
     5br Home/Apartment
    HolidayLettings
    From
    $1,246
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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
93 º73
4
92 º63
1
87 º49
1
82 º49
6
78 º32
3
85 º56
1
83 º53
1
87 º60
1
92 º70
10
94 º74
7
93 º64
5
94 º73
8
Sep
Oct
Nov
Dec
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Rainy days

This climate histogram shows you the weather patterns in Gulfport. The hottest month in Gulfport is July, when temperatures peak at 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.

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What Expert Travelers Think

  • — I love AllTheRooms because it is not only local homes for renting, and not only hotels, but everything combined. When I am about to book a place to stay, I usually spend a couple of hours looking through both hotel sites and local home sites, comparing the prices and places.

    Alli Sims
    Alli SimsAlli Sims
    Visit Alli Sims

  • — I love how AllTheRooms shows a map with room price tags straight away when you search, it makes it so quick and easy to choose the right hotel, at the right price in the right location. Perfect for those with busy lifestyles! The AllTheRooms website is so user friendly. WiFi. Brilliant!

    Amanda Alston
    Amanda AlstonAmanda Alston
    Visit Amanda Alston

  • — 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
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Vacation Rentals in Gulfport

Browse accommodations from all your favorite providers including Airbnb, RedAwning, Priceline and more at AllTheRooms.com. We have 606 vacation rentals, hotels and other places to stay in Gulfport ranging from low-cost options to extravagant places to stay. For those wanting to save money, the cheapest place to stay in Gulfport comes in at $15 per night. A typical rental in Gulfport costs on average $244 per night.

If you want to stay connected during your trip, then you can choose from over 384 accommodations in Gulfport that have WiFi. We have 44 accommodations that come with breakfast included. Fitness fanatics can get a workout in during their stay by choosing from 19 accommodations that have gym facilities. If you are driving to Gulfport, you'll want to pick from 374 places to stay that provide parking. 41 hotels and vacation rentals have a a pool or jacuzzi

If you're traveling with a furry friend, then be sure to choose one of the 190 pet-friendly accommodations available.

431 of the accommodations in Gulfport have been reviewed by previous guests. They rated 76% as great. You can instantly book any of 238 places to stay right now.

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