Historic Key West Vacation Rentals

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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.

Enjoy the best of both worlds at Casablanca Grande, combining two unique living spaces into one spacious Key West getawa...
10/30/2026

Enjoy the best of both worlds at Casablanca Grande, combining two unique living spaces into one spacious Key West getaway! Perfect for extended family, friends, or a longer island escape, you'll have room to spread out while enjoying privacy and togetherness.

Walk to local restaurants, discover hidden neighborhood gems, and live like a local in beautiful Key West!

Available November 12 – December 9, 2026

Make the most of your extended stay at Casablanca Grande. Our reservations link is in the first comment.

Explore Casablanca Grande and Enjoy Our Best Rates.

Make your Key West getaway unforgettable.Enhance your stay with a dolphin-watching cruise or a guided snorkeling adventu...
10/30/2026

Make your Key West getaway unforgettable.

Enhance your stay with a dolphin-watching cruise or a guided snorkeling adventure through vibrant coral reefs. Get up close with marine life and experience the beauty of the Florida Keys!

Explore tours and book your next stay with our link in the first comment.

Robinson Crusoe CottageYour Key West escape starts here. This updated 1-bedroom cottage sleeps 4 and puts you within wal...
10/30/2026

Robinson Crusoe Cottage

Your Key West escape starts here. This updated 1-bedroom cottage sleeps 4 and puts you within walking distance of Duval Street, Mallory Square, and local favorites.

Book your island getaway today with our reservations link in the first comment.

Meet Jasmine Manor: Your Private Poolside Escape in Key West.Enjoy the best of both worlds when you reserve Magnolia Man...
10/29/2026

Meet Jasmine Manor: Your Private Poolside Escape in Key West.

Enjoy the best of both worlds when you reserve Magnolia Manor and Bougainvillea Manor together. This beautifully restored Conch-style home offers the perfect blend of togetherness and privacy, with two king bedrooms, separate kitchen or kitchenette spaces, and a shared pool at the heart of the property.

Perfect for families, friends, or couples traveling together!

Book your Key West getaway at Jasmine Manor and make island living unforgettable. Our reservations link is in the first comment.

From unforgettable excursions to must-try restaurants and dining reservations, our concierge team helps you experience K...
10/29/2026

From unforgettable excursions to must-try restaurants and dining reservations, our concierge team helps you experience Key West like a local while enjoying all the comforts of home.

Ready to plan your island escape? Book your Key West vacation rental today and let us help you make every moment memorable!

Explore Our Concierge Services with our link in the first comment.

Key West adventure awaits—reserve your stay today!

Casablanca Too is a beautifully updated one-bedroom, one-bath duplex offering comfort, style, and a convenient location ...
10/29/2026

Casablanca Too is a beautifully updated one-bedroom, one-bath duplex offering comfort, style, and a convenient location near Key West’s favorite attractions.

Whether you’re a remote worker seeking a change of scenery, a snowbird planning a seasonal getaway, or simply ready to embrace a slower pace, this inviting retreat is the perfect place to settle in and enjoy tropical living.

Available November 12 – December 12, 2026

1 Bedroom | 1 Bathroom | Sleeps 2

Make time for island adventures, laid-back afternoons, and the charm of Key West.

Learn more about Casablanca Too with our link in the first comment.

Reel Paradise | Monthly Rental in Old Town Key WestEnjoy a relaxing extended stay at Reel Paradise, a light-filled townh...
10/28/2026

Reel Paradise | Monthly Rental in Old Town Key West

Enjoy a relaxing extended stay at Reel Paradise, a light-filled townhouse in the private Grinnell Gardens community in Old Town Key West. Featuring 3 bedrooms, 2.5 bathrooms, and accommodations for up to 5 guests, this inviting retreat offers a comfortable blend of privacy, convenience, and island charm. Settle into the laid-back Key West lifestyle while enjoying the peace and serenity of a private community, with Old Town’s restaurants, shops, and local attractions nearby.

3 Bedrooms | 2.5 Bathrooms | Sleeps 5 | Monthly Rental
Use our link in the first comment to reserve your next extended stay.

Old Town porches have been doing the same job for a hundred years.Morning coffees. Late-afternoon breezes. Post-dinner c...
10/28/2026

Old Town porches have been doing the same job for a hundred years.

Morning coffees. Late-afternoon breezes. Post-dinner conversations.

They know what they're doing.

Catch up on your porch-sitting with today's Blog. Link in first comment.

La Maisonnette | Nightly Rental in Key WestEnjoy the charm of Old Town Key West at La Maisonnette, a cozy one-bedroom re...
10/28/2026

La Maisonnette | Nightly Rental in Key West

Enjoy the charm of Old Town Key West at La Maisonnette, a cozy one-bedroom retreat just one block from Duval Street and steps from the restaurants, bars, shops, and attractions that make the island special. The Ernest Hemingway Home and Museum is also nearby, making it easy to explore Key West on foot.

1 Bedroom | 1.5 Bathrooms | Sleeps 4

Bringing your pup? One dog up to 25 lbs is welcome with an additional fee and completed pet information addendum. See our reservations link in the first comment to book your stay.

Poinciana Garden | Key West Nightly RentalStay in the heart of Historic Old Town Key West! This charming getaway feature...
10/27/2026

Poinciana Garden | Key West Nightly Rental

Stay in the heart of Historic Old Town Key West! This charming getaway features 1 bedroom, 1 bathroom, and sleeps up to 3 guests.

Just two blocks from Duval Street and close to top attractions, restaurants, shops, and galleries..

Traveling with your pup? One dog up to 25 lbs is welcome for an additional fee with a completed pet addendum.

Just two blocks from Duval Street and close to top attractions, restaurants, shops, and galleries. See our reservations link in the first profile.

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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