Gaspar's Luxury Estate

Step into Gaspar’s Luxury Estate, a two-story, 5-bedroom, 4.5-bath masterpiece designed to host 14–17 guests in individually themed, pirate-luxe suites inspired by Tampa’s legendary pirate, José Gaspar. This Bayshore-inspired mini mansion seamlessly blends Tampa-inspired architecture with modern luxury, featuring a private courtyard, rooftop bar, and a signature catwalk reminiscent of Tampa’s iconic waterfront, Bayshore Boulevard.

Perfect for family vacations, intimate weddings and celebrations, bachelor/bachelorette getaways, golf trips, honeymoons, creative retreats, and Gasparilla headquarters, this estate is loaded with upscale amenities: a detached poolside game room, sparkling emerald pool and hot tub, putting green, wood-burning pizza oven, outdoor fireplace, and a gas grill for alfresco dining. Multiple recreational areas, both inside and out, ensure endless entertainment, from rooftop stargazing to friendly putt-putt competitions.

Whether you’re celebrating life’s milestones or commanding your own crew for Gasparilla’s pirate invasion, Gaspar’s Luxury Estate delivers the ultimate vacation in style, comfort, and adventure in the heart of Tampa, Florida.

There’s a reason bachelor parties make up nearly half of our stays.

Inspired by the legend of José Gaspar, Gaspar’s Luxury Estate was designed to feel like the private South Tampa hideaway of an impossibly wealthy, modern-day pirate—a little mysterious, unapologetically indulgent, and made for memorable nights with your favorite people.

Weathered woods, rich leather, sumptuous velvet, warm metals, dramatic chandeliers, and layered textures create an atmosphere of rugged opulence throughout the estate. It’s sophisticated without feeling formal, theatrical without becoming kitschy, and unlike any ordinary vacation rental in Tampa.

Whether your ideal bachelor weekend involves friendly competition, drinks by the pool, a game on the big screen, or late-night conversations tucked away in a hidden bar, the estate gives your group room to do it all—without ever leaving home.

Challenge the group on our PGA professional-designed putting green, pool table, poker table, or dartboard. Fire up the gas grill or wood-burning pizza oven, gather around the wood-burning fireplace, or settle into the hot tub beneath the outdoor television.

When the sun goes down, keep the night moving between the rooftop bar overlooking the pool, our siren-themed game room, and the hidden pirate speakeasy—perfect for cocktails, stories, and the conversations that only happen after midnight.

• PGA professional-designed putting green
• Large private pool and hot tub
• Outdoor television positioned above the hot tub
• Rooftop rustic bar overlooking the pool
• Hidden pirate speakeasy
• Siren-themed game room
• Pool table and poker table with custom pirate poker chips
• Xbox and PlayStation
• Dartboard and group games
• Large televisions throughout the estate
• Indoor and outdoor Sonos sound systems
• Wood-burning fireplace
• Gas grill and wood-burning pizza oven
• Fully stocked coffee, espresso, tea, and cocktail bar
• Five refrigerators throughout the estate for food, drinks, and everything needed to keep the weekend going

This isn’t simply a place for everyone to sleep. It’s the backdrop for the stories your group will still be telling years from now.