Ins and Outs of Key West

lola's place pool

Historic Key West Vacation Rentals is celebrating the ins and outs of Key West. Key West is so out it's in, for sure.  From fashion and passions to arts and entertainment. From street life to nightlife and everything in between. The best part? From fall and all the way through winter, inside flow outside and the outside feels right at home on the inside.  When you choose to reserve one of these boutique luxury vacation rentals from our collection, all you have to do is open up a set if double doors or, in some cases, an entire wall and let the sunshine in. 

Ashe House - Monthly Rental 3 Bedrooms 3.5 Bath Sleeps 6

Every step outside Ashe House leads to the richness of Key West’s charm and beauty––lush tropical foliage, picket fences, gingerbread trim––while indoors the home is stunningly renovated and plumped with island-living comfort.

Casablanca Grande - Nightly Rental 2 Bedrooms 2 Bath Sleeps 6

Pet-Friendly Casablanca Grande consists of the two neighboring vacation rentals "Casablanca" & "Casablanca Too", located at the edge of Old Town Key West and The Meadows in a quiet neighborhood, just a short bike ride to anywhere you want to go in Key West! This is a spacious vacation rental with the added bonus of off-street parking for 2 cars and a private 20‘x10’ heated pool and hot tub! Beautifully manicured grounds along with wonderful outdoor areas. Gas grill for cooking your fresh catch and outdoor dining as well.

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!

Lola's Place - Monthly Rental 2 Bedrooms 2 Bath Sleeps 4

Lola's Place features everything you might want or need for your monthly vacation in Key West, starting with a private, off-street parking spot (an absolute MUST in Key West) for your vehicle. The back pool area comes with a pristine, sparkling small heated pool (heated November through April) and offers a tranquil waterfall feature making it the perfect tropical oasis. There is plenty of poolside loungers and seating available to soak in some rays as well!

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

This newly updated 2 bedroom 1 bath first-floor condo 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. The Shipyard has an extra-large pool for its guests to enjoy with plenty of lounge chairs for you to work on your tan. After sightseeing, return to your Key West home and relax on your large outdoor patio. Chaise lounge chairs, a dining table with an umbrella and a gas grill are there for you to enjoy.

Steamplant 208 - 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.

The ins and out of Key West are at a premium in winter. While the rest of the country is cold and stuck indoors. With plenty of sunshine, Caribbean ambiance, fresh seafood, days if joy and nights of ooh-la-la, this truly is a winter wonderland. Try out how easy it is to make reservations on our website and get the inside scoop on Key West living from our incredible Vacation Planners. Come as you are to stay and play, work and learn and to experience what it's like to bask in our sunshine. In or out. Out or in. This is Key West living!