Gulfport, Florida
Charming Downtown Gulfport Escape | Snowbird Friendly
Pineapple House
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
Pineapple House
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
Availability & Pricing
For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.
| Date | Price (USD, excl. fees and taxes) | Availability | Min Stay (nights) |
|---|---|---|---|
| Aug 2, 2026 | $181 | Not Available | 3 |
| Aug 3, 2026 | $181 | Not Available | 3 |
| Aug 4, 2026 | $181 | Not Available | 3 |
| Aug 5, 2026 | $181 | Not Available | 3 |
| Aug 6, 2026 | $181 | Not Available | 3 |
| Aug 7, 2026 | $181 | Not Available | 3 |
| Aug 8, 2026 | $181 | Not Available | 3 |
| Aug 9, 2026 | $181 | Available | 3 |
| Aug 10, 2026 | $181 | Not Available | 3 |
| Aug 11, 2026 | $181 | Not Available | 3 |
| Aug 12, 2026 | $181 | Not Available | 3 |
| Aug 13, 2026 | $181 | Not Available | 3 |
| Aug 14, 2026 | $181 | Not Available | 3 |
| Aug 15, 2026 | $181 | Not Available | 3 |
| Aug 16, 2026 | $181 | Not Available | 3 |
| Aug 17, 2026 | $181 | Not Available | 3 |
| Aug 18, 2026 | $181 | Not Available | 3 |
| Aug 19, 2026 | $181 | Not Available | 3 |
| Aug 20, 2026 | $181 | Not Available | 3 |
| Aug 21, 2026 | $181 | Not Available | 3 |
| Aug 22, 2026 | $181 | Not Available | 3 |
| Aug 23, 2026 | $181 | Not Available | 3 |
| Aug 24, 2026 | $181 | Not Available | 3 |
| Aug 25, 2026 | $181 | Not Available | 3 |
| Aug 26, 2026 | $181 | Not Available | 3 |
| Aug 27, 2026 | $181 | Not Available | 3 |
| Aug 28, 2026 | $181 | Not Available | 3 |
| Aug 29, 2026 | $181 | Not Available | 3 |
| Aug 30, 2026 | $181 | Not Available | 3 |
| Aug 31, 2026 | $181 | Not Available | 3 |
| Sep 1, 2026 | $181 | Not Available | 3 |
| Sep 2, 2026 | $181 | Not Available | 3 |
| Sep 3, 2026 | $181 | Not Available | 3 |
| Sep 4, 2026 | $181 | Not Available | 3 |
| Sep 5, 2026 | $181 | Not Available | 3 |
| Sep 6, 2026 | $181 | Not Available | 3 |
| Sep 7, 2026 | $181 | Not Available | 3 |
| Sep 8, 2026 | $181 | Not Available | 3 |
| Sep 9, 2026 | $181 | Not Available | 3 |
| Sep 10, 2026 | $181 | Not Available | 3 |
| Sep 11, 2026 | $181 | Not Available | 3 |
| Sep 12, 2026 | $181 | Not Available | 3 |
| Sep 13, 2026 | $181 | Not Available | 3 |
| Sep 14, 2026 | $181 | Not Available | 3 |
| Sep 15, 2026 | $181 | Not Available | 3 |
| Sep 16, 2026 | $181 | Not Available | 3 |
| Sep 17, 2026 | $181 | Not Available | 3 |
| Sep 18, 2026 | $181 | Not Available | 3 |
| Sep 19, 2026 | $181 | Not Available | 3 |
| Sep 20, 2026 | $181 | Not Available | 3 |
| Sep 21, 2026 | $181 | Not Available | 3 |
| Sep 22, 2026 | $181 | Not Available | 3 |
| Sep 23, 2026 | $181 | Not Available | 3 |
| Sep 24, 2026 | $181 | Not Available | 3 |
| Sep 25, 2026 | $181 | Not Available | 3 |
| Sep 26, 2026 | $181 | Not Available | 3 |
| Sep 27, 2026 | $181 | Not Available | 3 |
| Sep 28, 2026 | $181 | Not Available | 3 |
| Sep 29, 2026 | $181 | Not Available | 3 |
| Sep 30, 2026 | $181 | Not Available | 3 |
| Oct 1, 2026 | $181 | Not Available | 3 |
| Oct 2, 2026 | $181 | Not Available | 4 |
| Oct 3, 2026 | $181 | Not Available | 4 |
| Oct 4, 2026 | $181 | Not Available | 4 |
| Oct 5, 2026 | $181 | Not Available | 4 |
| Oct 6, 2026 | $181 | Not Available | 4 |
| Oct 7, 2026 | $181 | Not Available | 4 |
| Oct 8, 2026 | $181 | Not Available | 4 |
| Oct 9, 2026 | $183 | Not Available | 4 |
| Oct 10, 2026 | $183 | Not Available | 4 |
| Oct 11, 2026 | $181 | Not Available | 4 |
| Oct 12, 2026 | $181 | Not Available | 4 |
| Oct 13, 2026 | $181 | Not Available | 4 |
| Oct 14, 2026 | $181 | Not Available | 4 |
| Oct 15, 2026 | $181 | Not Available | 4 |
| Oct 16, 2026 | $183 | Not Available | 4 |
| Oct 17, 2026 | $183 | Not Available | 4 |
| Oct 18, 2026 | $181 | Not Available | 4 |
| Oct 19, 2026 | $181 | Not Available | 4 |
| Oct 20, 2026 | $181 | Not Available | 4 |
| Oct 21, 2026 | $181 | Not Available | 4 |
| Oct 22, 2026 | $181 | Not Available | 4 |
| Oct 23, 2026 | $183 | Not Available | 4 |
| Oct 24, 2026 | $183 | Not Available | 4 |
| Oct 25, 2026 | $181 | Not Available | 4 |
| Oct 26, 2026 | $181 | Not Available | 4 |
| Oct 27, 2026 | $181 | Not Available | 4 |
| Oct 28, 2026 | $181 | Not Available | 4 |
| Oct 29, 2026 | $181 | Not Available | 4 |
| Oct 30, 2026 | $183 | Not Available | 4 |
| Oct 31, 2026 | $183 | Not Available | 4 |
What this home offers
Where you’ll be
Gulfport, Florida, 33707, US
Our promise to you
Lower prices, every time
Direct line, real care
Not just a transaction
You’ll save $3,000+ booking direct!
Direct
Best price
$12,500
Airbnb
$18,500
Vrbo
$15,500
Booking.com
$18,500
Lower prices, every time
Pay less than you would anywhere else. No middlemen or platform fees.
Direct line, real care
Book with the team that actually runs the property. Faster answers, better service, real accountability.
Not just a transaction
We go further for direct guests. We’re building a relationship, not closing a booking.
Things to know
Check-in & check-out
Check-in after 4:00 PM.
Check-out before 10:00 AM.
Property rules
Children welcome (2–12 years).
Infants welcome (under 2).
Maximum 6 guests.
No pets allowed.
No parties or events.
Number and age of guests
Pets
Events
Smoking
Check-in & check-out
Cancellation policy
Contact us for cancellation policy details prior to booking.