Redefining the art of hospitality, Historic Key West Vacation Rentals cements its status as the gold standard in island accommodations
KEY WEST, Fla., — The soothing sound of swaying palm fronds. The soft caress of a salt-kissed breeze over a turquoise sea. A sun-dappled patio where a private pool awaits. A vivid daydream? Certainly for many, but reality for those who carve out unforgettable experiences with Historic Key West Vacation Rentals.
Recently featured in Condé Nast Traveler, this locally owned company redefines the art of hospitality in Key West — creating something well beyond a vacation. Led by Brenda Donnelly, an exceptional team helps create the ultimate island getaway where dreams play out each day in paradise.
Where luxury meets local charm
Every property tells a story, and at Historic Key West Vacation Rentals, guests become the main character in a unique island tale. From restored Conch-style cottages to sleek, modern retreats, each handpicked home blends the charm of Old Town with contemporary comforts. Whether it’s a romantic escape or a lively family reunion, guests will find that perfect fit. From cozy one-bedroom bungalows to sprawling six-bedroom estates complete with private pools, chef-ready kitchens and outdoor spaces that beg for a sunset toast, there’ s home for every heart.
Following are just a few options:
Monthly
Keen on spending a month enjoying your own exclusive island? The Escape at Sunset Key offers a once-in-a-lifetime opportunity to blend luxury and serenity. This beautiful 2BR, 3BA home offers ocean vistas, upscale amenities and unforgettable sunsets.
Imagine basking in the sun for a month or more from a prime vantage point at newly renovated Sunny Daze Cottage, a darling 2BR, 2BA cottage steps from Old Town Key West. Relax on a private brick patio and enjoy upscale finishes in this bright, cheerful, pristine island paradise.
Nightly
Located in Key West’s coveted Old Town, Chick-a-Pea Cottage puts guests right in the middle of it all … yet away from it all at the same time. Perfect for families (including four-legged members), this 4-bedroom refuge comes complete with a furnished cabana, lounge air and a private pool with waterfall feature.
A fabulous blend of historic charm and modern luxury, the enchanting Southard Comfort offers a quintessential Key West experience. Unique architecture and artwork exude a distinctive local ambience, and a private backyard with cocktail pool and outdoor shower beckon. Spacious, stylish and a just short walk from the Historic Seaport and Duval Street — this 3BR, 2.5 BA home is comfort redefined.
But what truly sets these properties apart? It’s more than a place to stay — it’s feeling welcomed into a feathered nest where every need is met.
The concierge experience
Vacations shouldn’t be stressful, and that’s where Donnelly’s team shines. From the moment a guest books, the Historic Key West concierge team snaps into action. Want to secure the best table at a hidden-gem restaurant? Done. Dreaming of a private snorkeling tour or a day of deep-sea fishing? Consider it arranged. Planning a surprise celebration? They’ll make it magical.
“Our guests deserve more than just a stay — they deserve a curated experience,” said Donnelly. “We’re here to take care of every detail so you can focus on creating memories.”
Why book with Historic Key West Vacation Rentals?
Unrivaled locations: Nestled in the heart of Old Town, each property offers easy access to iconic Key West attractions such as Duval Street, Hemingway’s Home, and Mallory Square. Yet guests also discover tranquil hideaways where they can truly relax.
Authentic hospitality: As Key West locals, Donnelly and her team know every nook and cranny of the island. Guests can gather insider tips on everything from the best Cuban coffee spots to the quietest beaches.
Tailored experiences: No two vacations are the same. The Historic Key West team’s personalized approach ensures each Key West adventure matches a guest’s unique vibe — whether that’s lounging by the pool or embarking on adrenaline-packed watersports.
A renowned reputation: Recently spotlighted in Condé Nast Traveler for its high-touch service and meticulously maintained properties, Historic Key West Vacation Rentals has cemented its status as the gold standard in island accommodations. “We’re more than just a vacation rental company,” said Donnelly. “We’re storytellers, dream weavers and passionate ambassadors of Key West. When you stay with us, you’re not just a guest — you’re part of our island family.”