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.

Escape to Seas the Day, where turquoise waters, island charm, and laid-back living come together for the perfect Key Wes...
10/22/2026

Escape to Seas the Day, where turquoise waters, island charm, and laid-back living come together for the perfect Key West vacation.

Your Island Getaway Includes:
A refreshing shared community pool
Lush, beautifully landscaped grounds
Access to a waterfront park, playground, and amphitheater
Walking distance to Fort Zachary Taylor State Park’s sandy beaches and turquoise waters
A short stroll to local shops, restaurants, and lively bars

Whether you're soaking up the sunshine, exploring the island, or relaxing poolside, this charming retreat is the perfect home base for your Key West adventures.

NIGHTLY RENTAL DETAILS

2 Bedrooms
1 Bathroom
Sleeps up to 4 Guests
Available November 2026 – January 2027
Nightly Vacation Rental

Winter dates are calling. Don't miss your chance to enjoy the sunshine and charm of Key West. Message us today for nightly rates, availability, and booking information. Link for reservations in the first comment.

Discover the home, history, and legacy of one of America’s most celebrated authors at the Ernest Hemingway Home & Museum...
10/22/2026

Discover the home, history, and legacy of one of America’s most celebrated authors at the Ernest Hemingway Home & Museum.

Explore the beautifully preserved residence where Hemingway lived and wrote, discover fascinating stories about his life and literary achievements, and wander through the lush tropical gardens. Don’t forget to say hello to the famous six-toed cats that call the property home!

Whether you’re a literature lover or simply soaking up the history and charm of Key West, this iconic landmark deserves a spot on your island itinerary.

Make the Hemingway Home a must-see on your next Key West getaway!

Planning your escape? Book your stay with Historic Key West Vacation Rentals and experience the island like a local! Visit our link in the first comment.

Meet Frangipani Cottage, your new go-to for a laid-back island escape! Perfect for couples or solo travelers, this charm...
10/22/2026

Meet Frangipani Cottage, your new go-to for a laid-back island escape! Perfect for couples or solo travelers, this charming retreat puts you just steps from the excitement of Key West while offering a peaceful place to unwind after a day of exploring.

1 Bedroom
1 Bathroom
Sleeps 2 Guests

Whether you're planning a romantic getaway or a solo adventure, Frangipani Cottage is ready to welcome you to island life!

NEW NIGHTLY RENTAL! Start planning your Key West escape today and reserve your stay at Frangipani Cottage with our link in the first comment.

Ready for a vacation filled with comfort, connection, and relaxation? Cloud 9 is the perfect place to gather with family...
10/21/2026

Ready for a vacation filled with comfort, connection, and relaxation? Cloud 9 is the perfect place to gather with family and friends. Enjoy plenty of room for entertaining, game nights, preparing delicious meals, or simply unwinding after a day of adventure. With 3 bedrooms and 3 bathrooms, everyone can enjoy their own private space while making unforgettable memories together.

AVAILABLE DECEMBER 31 – JANUARY 31

3 Bedrooms | 3 Bathrooms‍ | Sleeps 7

Cloud 9 – Nightly Rental. Book your stay and experience vacation bliss with our link in the first comment.

Here's your sign you needed a Key West vacation:You know which rooster wakes up first.He lives down the block. He starts...
10/21/2026

Here's your sign you needed a Key West vacation:

You know which rooster wakes up first.

He lives down the block. He starts before the others. And somehow you've grown fond of him.

Read all about rooster life in Key West in today's Blog. See the link in the first comment.

Imagine starting your day by the pool, preparing meals in a gourmet kitchen, and soaking up the island lifestyle in your...
10/21/2026

Imagine starting your day by the pool, preparing meals in a gourmet kitchen, and soaking up the island lifestyle in your own private oasis. With stylish décor, a sparkling saline pool, an outdoor kitchen, and a convenient Key West location, Hello Gorgeous is the perfect place to settle in and stay awhile!

NEW MONTHLY RENTAL
3 Bedrooms | 3.5 Bathrooms | Sleeps 6

January or March 2027 could be yours.

Paradise is calling, and you may never want to leave.️

Click the link in the first comment to reserve your stay!

Start your Key West morning with a peaceful sunrise over the Atlantic Ocean at White Street Pier. Enjoy the gentle ocean...
10/21/2026

Start your Key West morning with a peaceful sunrise over the Atlantic Ocean at White Street Pier. Enjoy the gentle ocean breeze, beautiful coastal views, and a quiet moment before the island comes to life. It's the perfect way to embrace the slower side of island living!

Make your Key West getaway unforgettable with Historic Key West Vacation Rentals.

Locally Owned • Locally Managed
Old Town · Truman Annex · Historic Seaport

Plan your island escape today with our link in the first comment.

La Casita en Cima | Key West Monthly Rental Available December 2026 | 2 Bedrooms | 2 Bathrooms | Sleeps 6Trade the winte...
10/20/2026

La Casita en Cima | Key West Monthly Rental

Available December 2026 | 2 Bedrooms | 2 Bathrooms | Sleeps 6

Trade the winter chill for sunshine and island living! This bright, inviting Key West-style home offers the perfect blend of tropical charm, comfort, and privacy.

Take a dip in your private heated pool with a waterfall feature, surrounded by lush landscaping and a fenced yard.

Enjoy the covered lanai, spacious decking, and outdoor dining beneath a large retractable awning—perfect for relaxing or entertaining in the Florida sunshine.

Inside, hardwood floors, central air conditioning, a mini-split in the primary bedroom, and ceiling fans keep you comfortable year-round.

Use our link in the first comment to make La Casita en Cima your home away from home for a tropical winter escape.

A beloved local institution, Blue Heaven serves up Caribbean-inspired cuisine in a laid-back, open-air setting filled wi...
10/20/2026

A beloved local institution, Blue Heaven serves up Caribbean-inspired cuisine in a laid-back, open-air setting filled with island charm. Enjoy delicious food, live music, and the company of Blue Heaven’s famous roaming chickens!

Make it part of your Key West adventure and experience the island like a local with the link in our first comment.

Locally Owned • Locally Managed
Old Town · Truman Annex · Historic Seaport

Discover the magic of Key West at Nancy & Carl’s enchanting 3-bedroom home, Southard Comfort. Designed for relaxation a...
10/20/2026

Discover the magic of Key West at Nancy & Carl’s enchanting 3-bedroom home, Southard Comfort. Designed for relaxation and indoor-outdoor living, this unique property showcases the island’s architecture, local art, and unmistakable joie de vivre. From the welcoming front porch to the private backyard, every detail invites you to slow down and live like a local.

Available December 12–19, plus highly desirable winter dates in 2027.

Make this special island retreat your home away from home. Visit the link in the first comment to reserve your stay. https://www.historickeywestvacationrentals.com/vacation-rentals/southard-comfort

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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