8 Caribbean Homes For The Holidays

island days pool
By the Historic Key West Vacation Rentals Team

Historic Key West Vacation Rentals has the premier collection of boutique luxury homes and we're happy to present to you these eight Caribbean homes for the holidays! You've spent most of the year quarantined and landlocked while dreaming of an exotic, tropical getaway.  Key West may physically be a part of Florida, but it's a whole world away when you consider our relaxed atmosphere with a counter-culture vibe, blue waters and white beaches as the background. Just driving down from the mainland resets your senses and you soon get the feeling you're closer to the Caribbean than the Sunshine State!

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. The gorgeously remodeled kitchen comes with white granite countertops, all new stainless steel fridge, freezer, dishwasher, stove, oven, microwave plus toaster, blender and coffee maker! Downstairs you will also find a conveniently located half bathroom as well as a stackable washer\dryer. This maritime-themed home will always remind you that the ocean is just a few steps away!

Island Days - Monthly Rental 3 Bedrooms 3 Bath Sleeps 8

This is a golfer's delight in the close proximity to the Key West Golf Club. Stay and play or do simply nothing at all! There's a fully stocked kitchen with all the amenities you need to prepare gourmet meals or dine at several great and nearby restaurants. Separated from Key West only by the narrow Cow Key Channel, Stock Island is both an extension of its famed neighboring island and a destination unto itself. It's a holdout of “old Key West,” maintaining elements of the way the island used to be before tourism took over.

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. Built in the shotgun style, the home’s front door enters a hallway that extends to the back of the house, with a master bedroom and adjoining bath, as well as a guest room and adjacent, second bathroom built off the left side. This architectural device both harmonizes indoor and out space and ventilates the rooms, as was necessitated in days before air-conditioning.

Steamplant 207 - Monthly Rental 3 Bedrooms 3.5 Bath Sleeps 8

This luxury residence has a spacious open floor plan with travertine marble floors. Skylights and lofty 14-foot ceilings complement the 3126 square feet of interior living space. Add the expansive balconies and rooftop terraces and this home is one of the largest monthly vacation rentals in Key West. Each large bedroom has its own ensuite state of the art bath. The floor to ceiling sliding glass doors opens each bedroom to a private balcony. Extra-large walk-in closets will accommodate an extensive wardrobe. There's also a Viking Chef’s Kitchen for the culinary enthusiast of the family or for those traveling with a personal chef. 

Harry Truman Suite - Nightly Rental 2 Bedrooms 1 Bath Sleeps 5

Enjoy new and very comfortable living room furniture so you can lounge while you watch your favorite programs, sports, or use the free high-speed wifi on your electronic devices. Many of the island's best restaurants are only a short stroll away but if you prefer to stay in, your kitchen is complete with all the appliances, cookware and dishes you need. The Harry Truman Suite is steps from Duval Street, the Lighthouse, Southernmost Point, the Hemingway Home, shops, restaurants, and art galleries! Enjoy the brand new shared heated pool with a tranquil waterfall feature!

Margaret Truman Suite - Nightly Rental 2 Bedrooms 1 Bath Sleeps 5

This suite is furnished with a full kitchen, contemporary living room with new comfortable furniture, new ultra-comfortable mattresses with premium linens, bathroom with Travertine shower and in-suite washer and dryer, high-speed Wi-Fi, flat-screen TVs in every bedroom and a large flat-screen TV in the living room - newly renovated and immaculate!

Seas The Day! - Weekly Rental 2 Bedrooms 1 Bath Sleeps 4

This luxury boutique vacation rental is located in the Shipyard section of the Truman Annex facing Southard Street. Open up the French doors to your living room where you will find new and comfy furniture, a flat-screen tv, cable and wifi. There is a dining room set that seats 4 with a pass-through to the galley kitchen. Granite countertops and stainless steel appliances will make the family cook happy!

Solaris Cottage - Nightly Rental 1 Bedroom 1 Bath Sleeps 2

Located on a tiny lane, this is a perfect and spacious retreat for one to two adults. Solaris Cottage is an artist’s cottage – for real. Its owner is a nationally recognized artist and some of her works are displayed in the cottage. The kitchen has a full-size refrigerator and a 4 burner gas stove, blender, microwave, and a toaster. The living room has a comfortable sofa with chaise, television with cable, and free wifi. A large dining table is ideal for both dining and for setting up your laptop.

These eight Caribbean homes for the holidays are where you can safely enjoy a Thanksgiving feast with your family and friends, a tropical Christmas for your very special Santa and a socially distant end of the year celebration. It's as simple as a few clicks on our website or by phone with our very festive Vacation Planners with lots of holiday spirit!