10 Key West Places Decked Out For The Holidays

copa cabana deck
By the Historic Key West Vacation Rentals Team

Deck the halls, for sure, but this is the year to think outside the house for Christmas and New Year's. Historic Key West Vacation Rentals has a collection of luxury boutique cottages and homes where the insides open up onto the most beautiful gardens and oases in the Conch Republic. You're invited to think outside the house for your gatherings and festivities. 2020 is drawing to a close and that's something to get decked out about.

Solaris Pair-A-Dise - Nightly Rental 2 Bedrooms 2 Bath Sleeps 4

Solaris Pair-A-Dise consists of two separate nightly rental - "Solaris Garden" & Solaris Cottage." "Solaris Pair-A-Dise" allows couples traveling together to stay close, but also have their own private living room and kitchen. Open the doors from your bedroom and step out onto the side shared deck area under the giant Banyan tree. Solaris Cottage is also available for Thanksgiving!

Casablanca Too - Nightly Rental 1 Bedroom 1 Bath Sleeps 2

Casablanca Too is the perfect vacation rental for two in sunny Key West, Florida! Take an evening dip in your private hot tub under the stars! In the back yard, there is a lush garden, a back deck with chaise lounge chairs, and an outdoor dining set.

Petite Maison - Nightly Rental 2 Bedrooms 2 Bath Sleeps 4

This is a charming, tasteful, designer two-story cottage that is all-new, yet the cottage has all the charm of a traditional Key West home. The living room has French doors that open up to a covered second-floor terrace where you can enjoy coffee or cocktails and enjoy the tropical breeze.

Poinciana Treetop - Nightly Rental 1 Bedroom 1 Bath Sleeps 3

Welcome to Poinciana Treetop, a sunny one-bedroom Key West vacation rental. Open the French doors from your bedroom and step out into the second-floor lanai. In the backyard, there is a shared gas grill, lush garden, back deck with chaise lounge chairs and outdoor dining set.

Casa Key West - Monthly Rental 3 Bedrooms 3 Bath Sleeps 6

One of the Grand Dames of Key West, this two-story family home, known locally as the "Amparo Avila House," combines the exceptional details of historic preservation with the modern amenities that today’s lifestyle demands. Your holidays will flow outside to an amazing pool on a super private patio that will have you saying “Florida!”

Castaway Cove - Monthly Rental 2 Bedrooms 1.5 Bath Sleeps 4

This beautifully appointed townhouse is nestled in the Key Cove community just a few minutes' drive or bike ride from downtown Key West and just steps away from access to the brilliant blue waters that surround Key West. Just outside of "Castaway Cove" sits a shaded patio table with seating for four and an umbrella. Take advantage of your own personal gas grill and cook up the day's catch each and every day!

Copa Cabana - Monthly Rental 2 Bedrooms 1.5 Bath Sleeps 4

Open the door to Key West’s past when you arrive at Copa Cabana, a quaint, 1923 “shotgun” house that was originally a cigar maker’s home, just a stone’s throw from where the Atlantic Ocean meets the Gulf of Mexico. The back porch overlooks a colorful cocktail pool with whirlpool jets. The wood deck includes a patio table with an umbrella that adds to the enjoyment of the comfy wicker settee and rocker on the back porch. There is a propane grill for grilling up your catch-of-the-day!

My Happy Place - Monthly Rental 2 Bedrooms 2 Bath Sleeps 4

My Happy Place is an exemplary renovation of a historic, Key West house. It retains its original character and wisdom, but with up-to-date comfort and high-quality interior design. The pool is right outside the backdoors, great for taking a dip, day or night! The front porch is fabulous for people watching and waving ‘Hey!’ as a good neighbor should.

Southern Skies - NEW Monthly Rental 3 Bedrooms 2.5 Bath Sleeps 6

Southern Skies is the Great Old Town location you want for your family or friends getaway!  A heated pool with a waterfall is private and luxurious. This home is just a 4-minute walk to the Southernmost Point of the United States, and just a few minutes by bike to Duval Street and all it has to offer.

Steamplant 210 - Monthly Rental 3 Bedrooms 3.5 Bath Sleeps 8

 Welcome to Steamplant 210! Two Level, 5 Star Luxury Residence with breathtaking panoramic views of Key West. The amazing private rooftop pool overlooks Key West for a dip at your leisure, day or night. Loungers, pool towels, grills and outdoor dining seating make for a perfect home away from home. Key West offers some of the best weather year-round, so in Key West outdoor living space is a must. The Residences at the Steamplant have expansive private balconies where you can start or end your day watching the sky.

It's easier than ever to experience these 10 Key West places decked out for the holidays. Reserve yours right on our website or with our top deck Vacation Planners. The holidays are for celebrating the love for our family and friends. This is a year for which we all still have lots to be thankful for.  Happy Holidays to you from Historic Key West Vacation Rentals!