In the colorful heart of Old Town Key West, where pastel homes whisper stories of literary giants and bohemian escapades, and where every breeze carries the scent of sea salt and bougainvillea, a rare offering has surfaced: not one, but two exquisite homes for sale, just a block from the pulsing rhythm of Duval Street.

Located at 421–423 Simonton Street, this dual-residence property is as versatile as it is vibrant—each home boasting three bedrooms, three-and-a-half bathrooms, and a private pool, making it a dream for investors, vacation homeowners, or anyone looking to immerse themselves in the singular rhythm of island life.

What makes this listing unique is not only its scale but its legal status: transient rental licensing, a golden ticket in Key West’s tightly regulated short-term rental market. Coupled with contemporary interiors, private outdoor retreats, and a walkable location steps from the city’s most storied strip, the Simonton Street compound is an opportunity where lifestyle meets investment with seamless grace.

Architecture & Design: Blending Tradition with Today

At first glance, the pair of homes at 421–423 Simonton Street appear as charming, well-kept island cottages—a nod to the Conch-style architecture that defines the Old Town landscape. Crisp white siding, metal roofs, and lush tropical landscaping lend the property a postcard-perfect façade. Yet step inside, and the experience evolves from quaint to quietly luxurious.

Both residences are fully updated, featuring open-concept floorplans that respect the need for flow and airiness in a tropical climate. High ceilings and plentiful windows maximize natural light, while subtle coastal finishes—light wood tones, stone countertops, and breezy textiles—enhance the island ambiance. The updated kitchens in both homes reflect a balance of style and utility, with stainless steel appliances, generous storage, and counter space for preparing everything from sunset cocktails to family feasts.

Each home includes three generously sized bedrooms, all with ensuite bathrooms—a rare and sought-after configuration that ensures comfort, privacy, and a touch of boutique hotel luxury. Whether serving as a family getaway or as a high-performing short-term rental, the layout is optimized for flexibility and peace of mind.

Outdoor Living: Palms, Pools, and Privacy

Key West is a place where outdoor space is more than just a luxury—it’s an extension of the lifestyle. The homes at 421–423 Simonton Street embrace this ethos completely. Each house features its own private pool and secluded lounging area, bordered by palms, plumeria, and flowering vines. Here, morning coffee becomes a ritual under the rustle of leaves, and afternoons are best spent cooling off in the water after a bike ride along the coast.

The outdoor spaces are designed with relaxation and functionality in mind. Whether reading under a shady pergola, dining al fresco with friends, or watching the stars rise over the property’s canopy, the homes offer sanctuaries of calm within steps of the island’s vibrant energy.

For those who intend to rent, these backyard oases are powerful marketing tools—photogenic, private, and filled with the charm that keeps travelers returning to Key West year after year.

Location: One Block from the Beat of Duval

Duval Street needs little introduction. It is Key West’s beating heart, where locals and tourists mix among historic saloons, modern cocktail bars, art galleries, music venues, boutique shops, and world-renowned restaurants. To be within a single block of this storied avenue is to live at the epicenter of the island’s culture and energy—yet, remarkably, Simonton Street offers a quieter, more residential buffer, allowing for both access and escape.

From this address, it’s possible to stroll to the Hemingway House, Southernmost Point, or Mallory Square for the island’s legendary sunset celebrations. Yet the neighborhood itself retains a more relaxed residential charm, making it just as suitable for tranquil living as it is for tourism-driven rental strategies.

Bike paths, beach access, and marinas are all within close reach, making the property a perfect launching point for exploration, whether by foot, two wheels, or sail.

Investment Value: Transient Licensing and Proven Performance

Perhaps the most compelling feature for savvy buyers is the transient rental license attached to both homes. In Key West, such licensing is tightly regulated and increasingly scarce, making properties that carry it especially valuable. This designation allows the homes to be rented on a nightly or weekly basis—flexibility that dramatically increases earning potential compared to standard long-term rentals or owner-occupied arrangements.

According to recent records, both homes boast strong rental histories, performing well year-round thanks to their central location, upscale amenities, and independent structures. The appeal for group travel—families, couples, destination weddings, or friends traveling together—is undeniable, particularly when each party can enjoy private bedrooms, individual pools, and shared access to local attractions.

Add in the fact that Key West remains one of Florida’s most consistent tourism markets, with robust hotel occupancy rates and limited real estate inventory, and the Simonton Street homes become not just desirable, but strategic. The dual-residence format also allows for a mix of personal and rental use. One unit can serve as a private retreat while the other operates as a high-performing income stream.

Market Context: Scarcity Meets Demand

The real estate market in Key West has evolved significantly over the last decade, with a distinct trend toward high-end, low-inventory listings in the Old Town core. Buyers—both domestic and international—are increasingly drawn to properties that blend lifestyle with return on investment. In this environment, listings that offer multiple units, legally supported rental income, and proximity to attractions are few and far between.

Compared to other Florida vacation markets, Key West holds a unique appeal: its historic architecture, island independence, strong arts scene, and international character make it a destination of enduring charm. Moreover, strict zoning and licensing limitations prevent overdevelopment, preserving the ambiance that makes properties like 421–423 Simonton Street so special—and so difficult to replicate.

Ideal Use Cases: Personal, Commercial, or Hybrid

Who is the ideal buyer for a property like this? The beauty lies in its flexibility.

• For investors, it’s a dual-income machine in a high-demand market with the legal infrastructure to scale.
• For vacation homebuyers, it’s the chance to own a piece of paradise and cover carrying costs through rentals—without ever needing to give up personal usage.
• For those seeking a legacy property, it’s a space where families can return year after year, and where memories are made across generations.

The two-residence layout also opens possibilities for multigenerational living, corporate retreats, or executive accommodations. With their mirrored amenities, each home can stand on its own while still complementing the other.

Impression

The offering at 421–423 Simonton Street encapsulates everything that makes Key West an aspirational destination and a smart place to invest. These are not just homes—they’re curated experiences, shaped by architecture, refined by interior design, and animated by their setting among the palm-lined streets of Old Town.

With transient licenses in hand, pools in the backyard, modern comforts throughout, and Duval Street mere steps away, the property transcends typical definitions. It’s not just residential. It’s not just commercial. It’s both—and in a market where such hybrids are increasingly rare, that’s where the true value lies.

As Key West continues to evolve while preserving its soul, opportunities like this will only become more elusive. For those ready to make a move, the time is now, the place is here, and the possibilities are endless.

Property Details

Address: 421–423 Simonton St, Key West, FL 33040

Units: Two standalone homes

Each Unit Includes: 3 Bedrooms, 3.5 Bathrooms, Private Pool, Outdoor Lounge Area

Licensing: Transient Rental License (Active)

Proximity: One block off Duval Street

No comments yet.