8 Boutique Luxury Upgrades For Your Key West Holiday Getaways

a Christmas wreath at Lemonade Mermaid Vacation Rentals in Key West.
By the Historic Key West Vacation Rentals Team

Key West is known for its community spirit where all are welcome to join in joyous celebrations of Thanksgiving, Christmas and New Year's. These are the times we decorate for the season and regale locals and visitors alike with art, fine food and holiday libations. Let this be the year to experience our independent and spirited tropical paradise with family and friends, as a couple or a solo traveler.  It's a beautiful time of year that combines our history, climate, natural beauty, culture, diversity, and historic preservation in our romantic setting. Enhance your holiday spirit among the flora and fauna as you wander through Old Town. Celebrate where you'll be removed from the rest of the world and the stresses of the year.  Choose from among these eight boutique luxury upgrades for your Key West holiday getaways.

Casablanca Too - Nightly Rental 1 Bedroom 1 Bath Sleeps 2

Casablanca Too is the perfect get-a-way vacation rental for one or two! Casablanca Too is one half of an impeccably maintained duplex that is located on the edge of Historic Old Town and The Meadows. This is a spacious vacation rental with the added bonus of off-street parking and a private hot tub! Beautifully manicured grounds along with the wonderful outdoor areas set this property apart from others.

Castaway Cove - Monthly Rental 2 Bedrooms 1.5 Bath Sleeps 4

Castaway Cove is a recently renovated monthly rental (28-night minimum) and comes with all the comforts you would find at home - and then some! The home boasts hardwood bamboo flooring throughout and has an open floor plan downstairs. Go on daily water adventures and soak up the sunshine out in the soothing waters of the Atlantic Ocean. Spend evenings gazing at the beautiful Key West sunsets out in your kayak. 

Island Days - Monthly Rental 3 Bedrooms 3 Bath Sleeps 8

This is a golfer's delight in close proximity to the Key West Golf Club. It's the ideal location for a quick trip to your boat and spending the day away on the crystal waters of the Atlantic or Gulf. It's in great proximity to the Sunrise Marina, Oceanside and Stock Island Marinas. Stop in at the Hurricane Hole Marina and rent paddleboards, kayaks, jet-skis, or charter a fishing boat.

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

Through the numerous windows lie glimpses of greenery and sky that are tableaux of Key West’s unique island beauty. The décor favors a soft, beach-like palette of taupe, shell, sand, and driftwood, with textures like velvet, leather and woven fibers. A mix of wood panel and white-painted walls combine into a balance of coziness and brightness, as well as varied backgrounds for displaying tasteful works of art.

Petunia Cottage - Monthly Rental 2 Bedrooms 1 Bath Sleeps 4

This two-story, two-bedroom home with a beautifully updated, second-floor bath offers the kinds of privacy and outdoor space you might not expect to find in a historic Key West home. Yet, there it is. Explore the beautiful outdoor deck that opens through French doors from the spacious, well-appointed kitchen. Why, there’s even that desirable and private outdoor shower with stars and moonlight overhead each evening.

Poppy Cottage - Monthly Rental 1 Bedroom 1 Bath Sleeps 2

Recently renovated and updated to its owner’s discerning standards, Poppy boasts hardwood floors, a modern kitchen and bathroom, and a tucked-away queen-size bed that simply begs you to snuggle in. The home is light-filled and supremely private. And, we bet you can’t help smiling when you see the delightful cobalt blue retro refrigerator! It’s a touch of modern whimsy you won’t soon forget. Petunia is a two-bedroom, one-bath home located just behind Poppy. Both are superbly private and quiet, so why not consider taking them both and sharing a Key West season with the family?

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

The Steamplant is the second tallest building in Key West. Nowhere else can you step out of your secure, private elevator onto your one of a kind Key West rooftop terrace 70 feet above the island. Enjoy a daily sunset dip in your private elevated rooftop pool. This opulent residence at the Steamplant offers unparalleled stunning views like no others on the island.

As the old saying goes, 'tis the season to be jolly. Any of these eight boutique luxury upgrades will have you positively elated. Reserve your favorite right on our website or allow our very festive Historic Key West Vacation Rentals Vacation Planners to assist with your selection. Come on down for the holidays where we'll eat, drink and always be merry!