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.

Key West cottages for Christmas
These Key West Cottages are on Santa's Good List and you will be, too, when you reserve one for your yuletide fun. These are luxury boutique vacation rentals that are perfect for family fun, girls getaways, couples retreats and solo travelers. In fact, Key West...Read more
key west at christmas
The holiday season is upon us, and Key West invites you to share in our festive celebrations. The season kicks off on Wednesday, November 24th at 5 p.m. with the Lighting of the Harbor Walk of Lights at the Historic Seaport. The first Monday after...Read more
galveston getaway vacation rental
Enjoy a weekend in the sun, December 3-5, 2021, surrounded by close compadres or simply folks you’ve only just met because of a shared love of music and art. The festival's main event is an all-day concert Saturday. VIP and General Admission tickets still available,...Read more
parade of paws
Join the Florida Keys SPCA for the 8th annual Parade of Paws at the Higgs Dog Park on Saturday, December 11th from 10 am-2 pm. It will be a family-friendly, fun-filled day of live music, local vendors at the Holiday Bazaar, and the crowning of...Read more
key west lighted bike parade
The Key West Lighted Bike Parade will be Friday, December 3rd, 4– 8 pm. Enjoy strolling and shopping the BeLighted Holiday Village at Coffee Butler Amphitheater inside Truman Waterfront Park. The BeLighted Bike Ride leaves at 8 pm. This is just one of the upcoming...Read more
retreat in style den
Retreat in style this holiday season with this Key West charmer from our luxury boutique monthly rentals collection . Our new Retreat In Style Monthly Renta l is filled with natural light and modern amenities. A contemporary kitchen with waterfall island seating and high-end, stainless...Read more
serene lily vacation rental
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
Cloud 9 bedroom
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
the view from sea vista vacation rental
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
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