Historic Key West Vacation Rentals

Historic Key West Vacation Rentals Historic Key West Vacation Rentals offers luxury historic vacation rental homes in Key West Florida.

HISTORIC KEY WEST VACATION RENTALS

YOUR STAY IN PARADISE

VACATION SPECIALISTS! Well-trained vacation specialists will guide you through the important process of selecting just the right property for your stay. Whether your party is one of friends or family, or a group celebrating a special occasion, we are eager to help you find the ideal property among our exceptional selection of beautiful accommodations. Our staff is committed to offering a uniquely personal touch in helping plan ideal independent travel vacations. We are proud of our commitment to first-rate personal service and believe it sets us apart from the rest. We appreciate the fact that our guests are thrilled by the prospect of "living as the locals do" in a delightful tropical setting - enjoying our climate and culture. Staying in a private home is truly the only way to experience a destination. For travelers seeking full-service accommodations, including housekeeping and chef services, we are able to offer a number of special services upon request. Working directly with the owners we seek to create an atmosphere of hospitality that will make you feel instantly at home. Our owners take pride in offering historic, charming and comfortable homes that offer the relaxing Key West Lifestyle experience. Historic Key West Vacation Rentals is able to provide information about every aspect of the travel and rental experience, including the minute details of what to expect at our breathtaking botanical gardens, quirky tours, or historic walking tours through lush gardens and homes neatly tucked away in Old Town. Here at Historic Key West Vacation Rentals we make it our business to find vacation rentals of the highest standards that go above and beyond our guest's expectations. By providing the finest experience in vacation rentals we can ensure your vacation is successful no matter which of our properties you choose. Families, business persons and travelers from all walks of life come to this amazing island. Our team is dedicated to creating your ideal Key West vacation through friendly, efficient attention to every detail of the process.

October might just be one of the best times to escape to Key West.Warm days. Tropical breezes. Gorgeous evenings made fo...
09/28/2026

October might just be one of the best times to escape to Key West.

Warm days. Tropical breezes. Gorgeous evenings made for dining outdoors. Sunset celebrations. Art, music and plenty happening around the island. And, of course, all the October fun Key West is known for.

Fall in Love With Villa Azul

Save 5% on Your October Stay. Link in first comment to learn more about this special rate!

Stay in a charming historic Old Town cottage where you’re perfectly positioned to enjoy the best of Fantasy Fest. Walk t...
09/28/2026

Stay in a charming historic Old Town cottage where you’re perfectly positioned to enjoy the best of Fantasy Fest. Walk to Duval Street, boutique shops, lively bars, acclaimed restaurants, and the unforgettable energy that fills Key West during this iconic celebration.

When the sun begins to set, make your way to nearby Mallory Square for the island’s legendary sunset celebration. Then stroll back through Old Town and enjoy the magic of Key West after dark.

Historic Key West Vacation Rentals
Locally Owned • Locally Managed
Old Town ¡ Truman Annex ¡ Historic Seaport

Fantasy Fest 2026 — Stay steps from the action.

09/28/2026

A few things you learn rather quickly in Key West…

Time becomes more of a suggestion than a schedule.

A few blocks can take you anywhere worth going.

Bare feet and fine linen somehow feel perfectly appropriate.

Your golf cart becomes less of a vehicle and more of a way of life.

And “just one cocktail” has a remarkable tendency to turn into an evening beneath the palms.

That’s the beauty of Key West—
unhurried days, effortless style, and nowhere else you’d rather be.

Welcome to island time.
You’ll settle in beautifully.

09/27/2026

We're just one week away from the (Very Belated) Jerry Garcia Birthday Bash! Join us and The Grateful Diver on Sunday, October 4 from 1:00 - 7:00 PM at The Green Parrot for jams by the Grateful Dead played live by The Happy Dog as well as a streamed Grateful Dead concert🎶, Dogfish Head x Grateful Dead beers🍻, drink specials, a 50/50 raffle💸, and over $8,000 in silent auction and raffle prizes!

To add to the excitement, you can start securing your raffle tickets Right Now! Over the next week we'll be pre-selling raffle tickets around town - you can also shoot us a DM or stop by our Environmental Center at 631 Greene Street. Raffle and silent auction prizes include gift certificates to local restaurants and businesses, bundles, art pieces, dive packages, charters, vacation packages, and hotel stays with all funds going to benefit Reef Relief’s ocean conservation and education programs🌊🦈. You don't have to be physically present to win our raffle, so if you aren't able to come for the whole event no worries! Check our story over the next week to see specific participating businesses and raffle ticket pricing.

So come have a long, strange time next Sunday and let us get by with celebrating Jerry Garcia’s birthday a couple months late because the music never stopped. Hope to see you there!

NEW NIGHTLY RENTAL | Royal Poinciana CottageEscape to the effortless elegance of Key West at Royal Poinciana Cottage, an...
09/27/2026

NEW NIGHTLY RENTAL | Royal Poinciana Cottage

Escape to the effortless elegance of Key West at Royal Poinciana Cottage, an intimate island retreat designed for two.

1 Bedroom • 1 Bathroom • Sleeps 2

Tucked within the charming Conch Cottages, Royal Poinciana offers a private, romantic setting for a refined Key West getaway. The property features three individual cottages—Royal Poinciana Cottage, Margarita Cottage, and Robinson Crusoe Cottage—each offering its own distinct retreat.

Reserve Royal Poinciana for a secluded escape for two, or elevate your experience by reserving all three cottages for exclusive use of the entire property—perfect for families, friends, or a special Key West celebration.

Reservations are now open, including availability around some of Key West’s most sought-after events:
🏃 Southernmost Half Marathon
🎉 Goombay Festival
🎭 Fantasy Fest
🎬 Key West Film Festival

Reservation link in the first comment.

09/27/2026
Jasmine Manor: Togetherness & Privacy in ParadiseReserve both suites of the beautifully restored Conch-style Manor House...
09/26/2026

Jasmine Manor: Togetherness & Privacy in Paradise

Reserve both suites of the beautifully restored Conch-style Manor House and enjoy the best of both worlds—plenty of space to gather, with privacy when you want it.

Magnolia Manor and Bougainvillea Manor are rented together as Jasmine Manor, sharing a sparkling pool at the heart of the property. Each suite features its own king bedroom and kitchen or kitchenette, making this a perfect setup for couples, families, or friends traveling together.

Poolside relaxation
Two private suites
King bedrooms in each
Kitchen or kitchenette in each suite
Classic Key West Conch-style charm

Link in the first comment for reservation openings, including stays for the Goombay Festival and Fantasy Fest!

Address

1119 White Street
Key West, FL
33040

Opening Hours

Monday 10am - 6pm
Tuesday 10am - 6pm
Wednesday 10am - 6pm
Thursday 10am - 6pm
Friday 10am - 6pm
Saturday 10am - 6pm
Sunday 10am - 6pm

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