We love this charming transient rental cottage that just came on the market! Located on one of the most beautiful streets in Old Town, 617 Southard Street is ideally situated just one and a half blocks from the heart of Duval Street. If you are looking to invest in a furnished turnkey property—with a transient license and an established rental history—you should definitely give us a call.
Backyard Paradise!
Upon entering the classic white picket gate, your guests will know that they will be enjoying a quintessential Key West cottage. They can watch the world stroll by from the inviting front porch, just off the spacious master suite. Casual island-style furnishings adorn the light-filled, open plan living room and kitchen. A wall of glass opens to a covered dining veranda overlooking the sparkling pool and tropical garden. With a ground floor guest room, guest bath, and an upstairs sleeping loft, there is plenty of breathing room for family and friends in this unforgettable vacation rental.
Memorable Indoor/Outdoor Living.
With the best of Key West charm and indoor/outdoor island living, 617 Southard Street will undoubtedly keep your renters coming back year after year.
A million dollar view of the historic Key West lighthouse.A charming retreat just a block from Duval Street.
When most people think of a million dollar view in Key West, they typically think of a sparkling, Caribbean blue, sky and water vista. With a spectacular shot of the historic Key West lighthouse from the upstairs master suite, the delightful cottage at 327 Virginia Street certainly cashes in with its remarkable million dollar view.
It is all about Key West cottage charm!
At first glance, we were captivated by this charming property. We love the tropical garden surrounding the gated off-street parking. The Bahamian shutters and sculptural Bougainvillea beautifully enhance the front exterior of the home. A newly updated kitchen and cozy living room opens to the glimmering pool and covered outdoor dining. The sunny upstairs master suite—with its extraordinary view—has French doors opening to a private balcony. Housed in a separate structure, the pool-side guestroom features a vaulted ceiling. A separate office cottage, storage building, outdoor shower, and close proximity to Duval Street add to the desirability of this unique Key West home.
Keith & Dean
We love the bamboo waterfall cascading into the pool!
Five bedrooms, five baths, and elbow room for all!
CBS news recently reported that while most of the 76 million baby boomers are no longer caring for their children, more and more of them are becoming caretakers of an older generation. For those boomers lucky enough to retire in Key West, many of them are not only looking for a dream home that checks off all the boxes on their wish list, they are considering the needs of their elderly parents as well. Our spacious new listing at 1217 Packer Street offers a wonderful opportunity for a multi-generational family to balance the need for safety and convenience with the desire for privacy and independence.
The 4 off-street parking spaces are a rare find in Old Town!
With 2,500 square feet of living space—all on one level—and a 6,701 square foot lot, 1217 Packer Street boasts plenty of breathing room. The 3 bedroom/3 bath main house features a generous open floor plan, two large master suites, high ceilings, and great storage. Multiple French doors open to a sunny 28’ x 13.5’ pool, sparkling spa, outdoor dining, and tropical garden. The inviting 2 bedroom/2 bath guest cottage—with a private entrance, living/dining room, full-sized kitchen, and laundry room—overlooks the pool. Indoor/outdoor living at its best can be found in this diverse Old Town property.
We love the sparkling 28′ x 13,.5′ pool!
We love that 1217 Packer Street is the perfect home for a multi-generational family to experience the best in tropical island retirement.
Keith & Dean
Click here to enjoy a virtual tour of this very special home.
Big things don’t always come in small packages. In the case of the charming cottage at 530 Grinnell Street, they certainly do.
We love the gorgeous interiors.
Designed by Key West architect, Guillermo Orozco, the home masterfully maximizes its 800 square feet with an open floor plan and lofty vaulted ceilings. The stunning island inspired interiors were fashioned by Houston’s Blair Gordon Design. We love the Brazilian Ipe wood floors, Dade County pine walls, Caesarstone countertops, maple cabinets, top-end appliances, and custom built-ins. The magical bunkroom is a childhood fantasy come true.
The bunkroom is a kid’s dream come true.
The storybook island cottage never ceases to capture our attention when we are strolling to Sunday brunch at Azure. From the Stephanotis draped white picket fence, to the indigenous Lignum Vitae tree shading the inviting front porch, the cottage radiates curb appeal plus. It is no wonder that this award winning home has been featured in the pages of Coastal Living.
Keith & Dean
Click here to enjoy a virtual tour of this charming Key West cottage.
The Windsor Village Compound—tucked away behind a tropically landscaped gate on Windsor Lane—is one of Key West’s best kept secrets. Brick pathways wind through stunning gardens to eleven individually owned cottages nestled around a large and tranquil pool. Built in the 1950’s, it is one of the oldest compounds on the island. Peaceful living abounds in this community established for those 55 years of age and older. Just two-and-a-half blocks from the heart of Duval Street, the conveniently located Windsor Village sits high and dry near the top of the highest point in Key West, Solares Hill.
The lushly landscaped grounds and community pool are beautiful.We love the vaulted wood ceiling and accent window.
Ideal for a couple or single person looking for a charming Key West pied-à-terre, 721-F Windsor Lane is a move-in-ready island cottage. Beautifully designed, the home utilizes its 591 square feet to maximum effect. A welcoming front porch invites you to while away the hours with a good book. Leading directly to the kitchen, the bright entry hall separates the living room from the bedroom. The living room features accent windows, a vaulted wood ceiling, and French doors leading to a private garden. Opening to an outdoor dining space, the sparking new kitchen showcases custom cabinets and stainless steel appliances. The light-filled bedroom features a high ceiling, French doors, and a newly renovated en suite bath. With the added bonuses of an outdoor shower, laundry, and storage loft, the small-scale cottage undoubtedly lives large. We adore this hidden Key West treasure!
The custom kitchen is gorgeous.
Windsor Village became commonly known as the Windsor Village Writer’s Compound when acclaimed writers, John Hersey, John Ciardi, Richard Wilbur, and Ralph Ellison purchased winter homes there in 1976. John Hersey was a celebrated writer and journalist, winning the Pulitzer Prize for his 1944 novel, A Bell for Adono. John Ciradi was a poet, translator and etymologist. Ciradi worked in television and radio with his show Accents on CBS and is reporting on NPR’s Morning Edition. Richard Wilbur is a poet and literary translator. The second U.S. Poet Laureate, Wilbur won the Pulitzer Prize for poetry twice, the National Book Award, and received the National Medal of Arts from President Clinton. Ralph Ellison was a novelist, literary critic, scholar, and writer. Ellison is best known for his novel, Invisible Man, for which he won the National Book Award in 1953.
