Merry Keysmas

Feeling lost about how to best spend your holiday? ‘Tis the season to celebrate all of the traditional joys associated with this time of year, with no snow shoveling involved! Key West is the perfect location to celebrate the season with family and friends for a holiday everyone will remember.

Escape from the cold and experience the holiday season a little differently here in Key West.

This Year Shovel Sunshine, Not Snow!

The winter chill might be on around the world, but here in sunny Key West you can expect temperatures in the high 70s or low 80s. Sometimes cold fronts bring a frost to the mainland of Florida, but here in Key West we stay frost-free! Rain is uncommon this time of year too so you can expect sunny skies and warm enjoyable temperatures.

Imagine enjoying a bike ride through Old Town to view the creative talent of Key West locals as they decorate with lights on everything from their homes, to fences, to boats… Palm trees make great Christmas trees too. Santa can even be found snoozing in a hammock or on a front porch.

Worried about stressful travel to Key West? Well don’t be, because getting to Key West has never been easier… United Airlines is now offering direct flights to Key West from Chicago and Newark throughout the Holiday Season.

Christmas in Paradise!

Give the ultimate gift of a last-minute Key West vacation to your spouse or family this year! We are currently offering a SUPER special of up to 60% off remaining rentals for Christmas, and we’ve extended this deal for January rentals as well. To make the deal even sweeter, our Concierge Team is offering Christmas Tree delivery and set-up, as well as all of the usual services (bike rentals, dinner reservations, fishing trips, etc).

Don’t hassle with traveling with gifts, just ship them to our office and we’ll deliver them right under your tree!

Enjoy More Churches and Bars

You are probably not surprised to hear that Key West offers more churches and bars per capita than anywhere else in the USA. For those looking for worship, you can attend a service at any of the many churches and synagogues. For those seeking happy hour and perhaps more, enjoy an eggnog martini or your preferred beverage at your favorite Key West watering hole. FYI Virgilos is open again!

Events = Lighted Everything!

December in Key West means the festive season is in full swing. The island buzzes with magical events for all to enjoy… and lots of lights!

Take a lighted trolley to view all the wonderful lights around Old Town.

Enjoy the annual lighted boat parade.

Take a tour of the Historic Inns of Key West.

Ring in the New Year… Key West style!

Spend your last nights of 2017 sipping on bubbly in Paradise! Key West is the best place to celebrate New Year’s Eve – watching the famous drag queen Sushi drop from a shoe at 801 Bourbon or the famous Conch Shell drop at Sloppy Joes bar. Duval street is closed to cars for the big party. The best part – sipping champagne in 75 degree weather. We’re also providing special welcome and celebratory gifts to guests staying with us for New Years.

Consider spending this holiday season with us in Key West and make a special holiday memory or plan a surprise trip for your spouse or family as a Christmas gift. Give us a call at 305-292-6266 or browse our available homes for last minute availability.

January is Fun in Key West!

There is never a bad time to visit Key West, but January may be the best month to enjoy the southernmost part of the United States. While the rest of the country is bundled up indoors, the month of January in Key West is traditionally in the mid-70s and sunny. Besides having superb weather, January in Key West is loaded with an abundance of exciting events for tourists and residents alike. Here’s a short list of exciting happenings taking place in Key West during the month of January:

  1. 30th Annual Regatta Race WeekimagesTaking place January 15-20, this thrilling must-see event features world-class yachting competition from all over the world. There will be upwards of 100 yacht teams competing for class Championships and is a fun time for the whole family. To view the action, fans can book seats on spectator boats ranging from excursion catamarans to historic tall ships or from land at Key West’s Atlantic-front restaurants, resorts and beaches.

  1. 12th Annual Key West Seafood FestivalunknownAs long as you’re not allergic to shellfish, you’ll absolutely love this event! Held at Key West’s Bayview Park on January 14 & 15, the Seafood Festival is sure to be a weekend of shell cracking, butter dipping fun. A family-friendly event with fresh Key West seafood, drinks, marine-related crafts, youth activities, and live music.

  1. Key West Food & Wine FestivalunknownGrab a wine glass and a fork, as you pair your favorite vino with Key West’s finest culinary delicacies. From January 25-29, enjoy premiere cuisine and wine brought to you by top chefs and restaurateurs in a flavorful schedule of events for food lovers. Highlights include neighborhood wine strolls, food and wine pairings, intriguing seminars and a grand tasting.

  1. 57th Annual Key West House & Garden Toursunknown-1Have you ever wanted to see the inside of Key West’s oldest and most exquisite homes? Here is your chance! Tour a series of elegant and unique private homes, ranging from luxurious restorations to creative renovations, and the interior design that complements each. March tours are offered 10 a.m. to 4 p.m. on January 13 & 14.

  1. 32nd Annual Key West Craft Showunknown-2Strengthen your craft game by joining the thousands of attendees browsing and buying creatively crafted items made by local artisans who gather to display their talents at this popular outdoor festival. Event held January 28 & 29 on Whitehead Street in historic Old Town Key West.


    It’s not too late to plan your January escape of the blistering winter experienced by most of the country. Come down for a long weekend, kick back for a week, or stay for the whole month! We still have some homes available for January, these homes include:

Gulfside Vistas

Stunning Third Floor 2 Bedroom, 2.5 Bathroom Waterfront Condominium in Truman Annex with Waterfront Community Pool Access. Available Weekly.


Suzy’s Parrot Perch

Charming Second Story 2 Bedroom, 1 Bathroom Apartment in Old Town Near Duval Street. Available Nightly & Weekly.


Octopus’s Garden

Beautiful 2-Story 3 Bedroom, 3 Bathroom Private Home at Coral Hammock Gated Community with Pool & Fitness Center. Available Nightly & Weekly.


Casita Angelita

Fully Renovated First Floor 2 Bedroom, 2 Bathroom Condo located just off Duval Street. Available Nightly & Weekly.


Nature’s Edge

Luxurious First Floor 2 Bedroom, 2 Bathroom Condo at Smathers Beach. Available Nightly & Weekly.



Visit our website: to see all of our available Vacation Rentals and to book your Key West stay for January, it will be here before you know it! See you in Paradise ?