Key West Vacation Guide

Key West is a VERY dog-friendly town! Furry friends are even allowed in some bars and restaurants on our island. There are also several dog parks and even a dog beach! If you wish to travel with your dog(s), we do have dog-friendly vacation homes available.

serene lily vacation rental

A Key West Home Perfect For Two Couples

Located where the Gulf meets the Atlantic, this home is perfect for two couples or a small family and it's a very welcome addition to our weekly rentals collection . Its open concept first floor is flooded with natural light. The updated white kitchen is...Read more
Categories: 
Key West Vacation Guide
Cloud 9 bedroom

Key West Vacation Inside Tips for Guests

We're sharing five guests' insider tips for your best historic Key West vacations. Word of mouth still remains the best advertising money can't buy and comments such as these really make our day. We know you'll enjoy reading them as much as we do and...Read more
Categories: 
Key West Vacation Guide
the view from sea vista vacation rental

Vacation In Key West With A Purpose

Vacation in Key West With A Purpose and enjoy a vacation that makes a difference. It's about the experience of giving back and making our Caribbean ecosystem protected and sustainable. Causes range from reef restoration and beach clean-ups to helping kids or spending time working...Read more
Categories: 
Key West Vacation Guide
Key West

Friendsgiving In Key West

Soon, the holidays will be upon us and we'll be making treks to visit family from near and far. It's also a great time to celebrate the season with the friends we've gathered on our journeys and our adventures. It's called Friendsgiving and Key West...Read more
Categories: 
Key West Vacation Guide
Cloud 9 pool

5 Dream Adventures In Key West

While most everywhere else is making preparations to winter up and hibernate until the spring thaw, Key West continues to be sunny and warm with breathtaking sites that draw crowds every night for the sunsets, arts, recreation and culinary spectaculars. Our Conch Republic is one...Read more
Categories: 
Key West Vacation Guide
Inn Cogneato pool

Inn Cogneato Cottage - Monthly Rental

Inn Cogneato is a beautifully renovated two-bedroom, two-bath home located in one of the oldest parts of Historic Key West. Surrounded by a white picket fence and with its gorgeous wood floors, this home is perfect for a couple that plans on entertaining visiting guests...Read more
Categories: 
Key West Vacation Guide
Reel Paradise

Reel Paradise

Reel Paradise invites its guests to enjoy the peace and serenity of island life. This beautiful home is so warm and inviting! As you enter the gate, you will pass by the shared pool and gardens on the way to your covered front porch. Step...Read more
Categories: 
Key West Vacation Guide
the pool at Dreaming On Duval

4 Guests' Inspirations For Fall Key West Vacations

Historic Key West Vacation Rentals has enjoyed seeing so many of our repeat guests we didn't get to see last year, and now we're even more anxious to see more of our guests we've come to cherish and enjoy. Even though the calendar may be...Read more
Categories: 
Key West Vacation Guide
The Truman Suites

The Truman Suites

The Truman Suites offers five separate fully equipped suites just a few steps from famous Duval Street. The two-story complex offers seven bedrooms, five bathrooms and sleeps up to 18. The Truman Suites collection includes 1-2 bedroom suites — Harry, Margaret, Martha, Bess Suites, and...Read more
Categories: 
Key West Vacation Guide
key west's southernmost point

5 Remote Working Breaks In Key West

This is the life. Remote working from a luxury boutique cottage or Conch home with the Caribbean and historic Key West as a part of your office decor. Historic Key West Vacation Rentals has the perfect home away from home for you and your friends...Read more
Categories: 
Key West Vacation Guide

Pages