5429 ESSEX AVENUE S, Gulfport, FL 33707

• 4 beds |
• 3 baths |
• 2,340 sqft

Property Description

Short-Term Rental investment opportunity in the heart of Gulfport’s Historic Art District! This fully furnished, Key West-inspired coastal retreat offers short-term vacation rental potential, breathtaking Boca Ciega Bay views, and an unbeatable walkable location just steps from downtown Gulfport’s restaurants, galleries, waterfront parks, nightlife, and popular Tuesday Farmers Market. Whether you’re seeking a high-performing Airbnb/VRBO property, second home, or full-time waterfront residence, this exceptional home delivers the perfect combination of lifestyle and income-producing potential. Guests and owners alike will love the private outdoor living spaces with panoramic water views overlooking Veteran’s Park—ideal for morning coffee, sunset cocktails, and entertaining in true Florida style. Inside, coastal elegance meets modern luxury with an open-concept layout designed for comfort and hosting. The gourmet kitchen features stone countertops, extensive cabinetry, abundant storage, and premium finishes perfect for entertaining vacation guests or everyday living. The luxurious primary suite serves as a private sanctuary with a professionally designed walk-in closet system and a spa-inspired ensuite bath complete with a whirlpool tub, dual vanities, and oversized enclosed shower. The third floor features private outdoor decks off the primary, second, and third bedrooms, offering incredible sunset views and refreshing coastal breezes that make Gulfport one of Tampa Bay’s most beloved waterfront communities. Built for durability, efficiency, and low-maintenance ownership, the home includes an elevator, impact-rated windows, Hardie plank siding, Trex decking, turf landscaping, and a whole-home solar system for significantly reduced electric costs. The oversized two-car garage provides ample room for vehicles, kayaks, jet skis, beach gear, or additional owner storage. Located just minutes from Downtown St. Petersburg, award-winning Gulf beaches, marinas, and Tampa Bay attractions, this rare turnkey short-term rental property is ready to generate income immediately while offering an incredible waterfront lifestyle. Opportunities like this in Gulfport’s Historic Waterfront District are exceptionally rare.

Listing Status:

Active

Date Added:

March 17, 2026

Data Last Updated:

July 26, 2026 at 11:23PM

Listing Office:

KELLER WILLIAMS ST PETE REALTY : 727-894-1600

Listing Agent:

Tricia Dooley : 727-460-0060

MLS ID:

TB8457726

Interior

• General: ElevatorOpen FloorplanPrimaryBedroom UpstairsSolid Surface CountersSolid Wood CabinetsStone CountersWalk-In Closet(s)
• Appliances: CooktopDishwasherDisposalDryerElectric Water HeaterExhaust FanMicrowaveRangeRefrigeratorWasher
• Laundry: Laundry Room
• Flooring: TileWood
• A/C: Central Air
• Heating: Central
• Eco/Green Feature: Solar

Exterior

• General: BalconyFrench DoorsSidewalkStorage
• Style: Key West
• Parking: Alley Access

Construction

• Roofing: MetalShingle
• Windows: Blinds
• General: BlockCement SidingThree Or MoreSlab

Location

• Road/Access: Paved
• Originating MLS: Stellar MLS
• County: Pinellas

Lot

• Zoning: BOCA CEIGA PARK BLK DLOT 1333-31-16-09612-004-0130
• View: Water
• Fencing: Vinyl

Utilities

• Utilities: Electricity ConnectedSewer ConnectedWater Connected
• Water: Public
• Sewer: Public Sewer

Financial

• Source: Stellar MLS
• Ownership: Fee Simple