5 Best Key West Spring Retreats

cloud 9 pool
by Historic Key West Vacation Rentals

While most are still dealing with colder weather, Key West is more than delighted to invite you to shovel sunshine. Spring in Key West is truly paradise. It's our delightful warmth and wonderful sunshine that create this twist that defies colder temperatures everywhere else. These are the days when snowbirds flock to our southernmost region while others must hibernate until a good thaw comes along. Key West is a much busier and happening place all year round. Historic Key West Vacation Rentals has just the right luxury accommodation to suit your needs for a spring vacation, a remote working paradise, and the most beautiful place with its stunning turquoise waters to host family and friends with no warm clothing in sight. Check out these five best Key West Spring Retreats that are all flip-flop ready.

Cloud 9 - Nightly Rental 3 Bedrooms 3 Bath Sleeps 7

If you are looking for a peaceful retreat that is close to everything, this is the ultimate home for you. You will be greeted by the home's stunning French doors, private pool, lounge area and second-story balcony.

Dreaming on Duval - Nightly Rental 5 Bedrooms 4.5 Bath Sleeps 10

As you enter the front gate of this luxury Key West nightly rental, you arrive in a private wonderland on the quieter end of Duval Street. Enjoy morning coffee or people watching on the elevated, partially covered front porch. The home’s backyard oasis includes a covered rear patio, a pool with waterfall feature and lush landscaping. 

Villa Luxe - Nightly Rental 3 Bedrooms 3.5 Bath Sleeps 7

The large outdoor area provides you with a quiet yet playful haven in a terrific location. The décor, like the property itself, combines contemporary Key West with jet-set sparkle. Spoil yourself in this luxury Key West vacation rental with a private pool the splendor of Villa Luxe!

La Maisonnette - NEW Nightly Rental 1 Bedroom 1.5 Bath Sleeps 4

Begin your stay with coffee or tea on your shared, covered front porch. Take a dip in the community's cocktail pool or have lunch in the garden patio area before heading out to sight-see.

Potter's Cottage - Nightly Rental 2 Bedrooms 2 Bath Sleeps 5

This cottage's large French doors open onto the partially covered deck where you can enjoy dining poolside. The fresh ‘catch of the day’ will taste great when cooked on the gas grill. 


Along with our fabulously mild temperatures and glorious blue skies, you'll want to get out for strolling, shopping, fresh seafood, arts, and entertainment. Run a marathon, take a tour of homes, enjoy sailing and snorkeling and experience our Key West spring events. Reserve your Key West vacation rental or contact our vacation planners when you call 305.296.1010. Be our guests this spring!