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Charming Downtown Gulfport Escape, Snowbird Friendly

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A small, single-story building with a teal roof and white trim, surrounded by a white picket fence and palm trees.
Living area
Dining
Private kitchen
Living area

Reviews

9.8 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 6

Popular amenities

  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Balcony
  • Internet access

Explore the area

View in a map
Gulfport, FL
  • Place, Gulfport Tuesday Fresh Market
    ‪1 min walk‬
  • Place, Gulfport Beach
    ‪3 min walk‬
  • Place, Gulfport Casino
    ‪3 min walk‬
  • Airport, St. Petersburg, FL (SPG-Albert Whitted)
    ‪12 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

2 Single Beds

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Kitchen
Office
Balcony
Garden

About this property

Charming Downtown Gulfport Escape, Snowbird Friendly

Summary:

Pineapple House


The Space:

Welcome to Pineapple House - A sunny retreat in the heart of downtown Gulfport.

Bright, welcoming, and perfectly placed, Pineapple House offers the ideal blend of coastal charm and small-town energy - making it a favorite for families and friends looking to stay close to the action while enjoying a comfortable, relaxed home.

Set on a quiet street just moments from downtown, this cheerful home captures the tropical spirit its name evokes. Inside, light-filled living and dining spaces make it easy to gather for meals, games, and conversation. The open kitchen is fully equipped for everything from quick breakfasts to shared dinners, while the casual breakfast bar invites slow mornings before heading out to explore. Younger guests will love the loft-style bedroom - a cozy hideaway perfect for relaxing after a day in the sun.

Step outside and enjoy the enclosed yard, offering a private space to unwind after beach days, festivals, or sunset walks.

Location is what truly sets Pineapple House apart.

You’re within easy walking distance of downtown Gulfport and Gulfport Beach, a calm, family-friendly shoreline along Boca Ciega Bay known for its waterfront park, fishing pier, playgrounds, and spectacular sunsets. The area is rich with local flavor - stroll to favorites like Pia’s Trattoria, O’Maddy’s Bar & Grille, Isabelle’s, and the lively Tiki Bar, all just minutes away.

Gulfport is celebrated for its artsy, welcoming community and year-round events. Time your stay to enjoy the Tuesday Fresh Market, evening Night Markets, the popular GeckoFest, or seasonal waterfront art festivals that bring live music, food vendors, and colorful energy to the downtown streets. For classic Gulf beaches, St. Pete Beach and Treasure Island are just a short drive away, offering sugar-white sand and turquoise waters.

Whether you’re planning a family vacation, a friends’ getaway, or a festival-filled retreat, Pineapple House places you at the center of Gulfport’s charm - sunny, walkable, and unmistakably coastal.

Things To Know

  • Bedroom 3 is a loft-style room with two twin beds
  • Free high-speed WiFi
  • Fully equipped kitchen with dishwasher
  • Beach towels provided
  • Private washer & dryer
  • Central air conditioning
  • Snowbird-friendly
    • Our prices include all fees. No hidden fees.

    Add dates for prices

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    House Rules

    Check in after 4:00 PM
    Minimum age to rent: 21
    Check out before 10:00 AM
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    Children

    Children allowed: ages 0–17
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    Events

    No events allowed
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    Pets

    No pets allowed
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    Smoking

    Smoking is not permitted

    Important information

    You need to know

    Property # 4907201vb
    If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
    This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
    Extra-person charges may apply and vary depending on property policy
    Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
    Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
    On-site parties or group events are strictly prohibited
    Host has indicated that there is a carbon monoxide detector on the property
    Host has indicated that there is a smoke detector on the property
    Safety features at this property include a fire extinguisher and a first aid kit
    This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

    About the area

    Gulfport

    Located in Gulfport, this holiday home is in the city centre and near the beach. Travellers eager for a bit of culture can stop by Salvador Dali Museum, while those wishing to experience the area's natural beauty can explore St. Petersburg - Clearwater Beaches and Upham Beach. Looking to enjoy an event or a game while in town? See what's happening at Tropicana Field or St. Pete's Historic Coliseum. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with cycling nearby.
    View more Holiday homes in St. Petersburg - ClearwaterOpens in a new window
    Map
    Gulfport, FL

    What's nearby

    • Gulfport Tuesday Fresh Market - 1 min walk - 0.1 km
    • Gulfport Beach - 3 min walk - 0.3 km
    • Gulfport Casino - 3 min walk - 0.3 km
    • Island Community Theatre - 4 min drive - 1.8 km
    • John's Pass Village & Boardwalk - 21 min drive - 12.2 km

    Getting around

    • St. Petersburg, FL (SPG-Albert Whitted) - 13 min drive

    Restaurants

    • ‪McDonald's - ‬17 min walk
    • ‪O'Maddy's - ‬4 min walk
    • ‪Pia's Trattoria - ‬2 min walk
    • ‪Stormrunners Tavern - ‬4 min walk
    • ‪Dunkin' - ‬13 min walk

    Frequently asked questions

    Is Charming Downtown Gulfport Escape, Snowbird Friendly pet-friendly?

    No, pets are not allowed at this property.

    How much does it cost to stay at Charming Downtown Gulfport Escape, Snowbird Friendly?

    As of 7 Jul 2026, prices found for a 1-night stay for 2 adults at Charming Downtown Gulfport Escape, Snowbird Friendly on 12 Jul 2026 start from £258, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

    How much is parking at Charming Downtown Gulfport Escape, Snowbird Friendly?

    On-site parking is available at the property.

    What time is check-in at Charming Downtown Gulfport Escape, Snowbird Friendly?

    Check-in begins at 4:00 PM.

    What time is check-out at Charming Downtown Gulfport Escape, Snowbird Friendly?

    Checkout is at 10:00 AM.

    Where is Charming Downtown Gulfport Escape, Snowbird Friendly located?

    Located in the heart of Gulfport, this holiday home is 0.2 mi (0.4 km) from Gulfport Beach and 2.7 mi (4.4 km) from Pasadena Shopping Center. St. Petersburg - Clearwater Beaches and Palms of Pasadena Hospital are also within 6 miles (10 km).

    Reviews

    9.8

    Exceptional

    Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
    Learn moreOpens in a new window
    Rating 10 - Excellent. 5 out of 6 reviews
    Rating 8 - Good. 1 out of 6 reviews
    Rating 6 - Okay. 0 out of 6 reviews
    Rating 4 - Poor. 0 out of 6 reviews
    Rating 2 - Terrible. 0 out of 6 reviews

    10/10

    Cleanliness

    10/10

    Check-in

    10/10

    Communication

    10/10

    Location

    10/10

    Listing accuracy

    Reviews

    Verified

    10/10 Excellent

    Walt C.

    Liked: Cleanliness, check-in, communication, location, listing accuracy
    We really liked how close this property was to the restaurants and bars.
    Stayed 4 nights in May 2026
    Verified

    10/10 Excellent

    Eric K.

    Liked: Cleanliness, location
    House fully equipped and comfortable. Excellent location.
    Stayed 7 nights in May 2026
    Verified

    10/10 Excellent

    Kristin G.

    Liked: Cleanliness, check-in, communication, location, listing accuracy
    The Pineapple House in Gulfport, FL, was perfect for our family's extended weekend celebration. The location was in easy walking distance to the beach, restaurants and shops in Gulfport. The property was chic, were equipped and we really appreciated the private parking at the facility. We highly recommend this cute house to future renters.
    Stayed 4 nights in Apr 2026
    Verified

    8/10 Good

    Tim J.

    Liked: Cleanliness, check-in, communication, location, listing accuracy
    Very nice and the location was really convenient. Day one was very hot inside. Appears that the temp is set at 78 upon check in. During the summer, it takes 24 hours for the AC to catch up. It was 80 in the unit for the remaining of the first day. Much better the rest of the visit. May be a good idea to turn down the thermostat the day before a guest arrives. Certainly understand the cost associated, but if a guest wanted to stay upstairs on the first night, it would be miserable. Not the way to start a trip. Love we didn’t have any check out procedures, thank you! The neighbor’s property was really not kept, don’t know a good suggestion for that. Loved the backyard parking. Thank you, we had a great time in Gulfport! Loved the town and the location.
    Stayed 4 nights in Jun 2026
    Verified

    10/10 Excellent

    Josh B.

    Liked: Cleanliness, check-in, communication, location, listing accuracy
    Unit was clean, comfortable and very convenient. A great spot in a great little community yet close to all the great beaches and attractions.
    Stayed 6 nights in Jun 2026
    Verified

    10/10 Excellent

    Shelly M.

    Liked: Cleanliness, check-in, communication, location, listing accuracy
    Only thing was no beach equipment, adding a few beach chairs if possible would be nice. Hope that is helpful. We loved the place and will definitely rent again!
    Stayed 4 nights in Apr 2026

    About the host

    Hosted by Casago Tampa

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    Premier Host

    They consistently provide great experiences for their guests
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