Birds Of A Feather Flock To Key West

open floor plan at ashe house monthly vacation rental
By the Historic Key West Vacation Rentals Team

Birds of a feather flock to Key West for the winter.  We refer to them as Snowbirds and we're happy to call them our friends.  Year after year, we enjoy hosting guests from Canada, New York, Connecticut, Boston, Chicago, Washington DC and other very cold destinations. We love reconnecting with them and we always look forward to the new Snowbirds who find us, as well. We're so excited for the season to start we've opened up even more availability for January 2021. There's room for everyone and for lots of family fun, girls getaways, couples retreats, mancations, solo travelers and pet guests, too. Which one of our luxury boutique homes is best for you?  Let's take a look. We won't be disappointed if you choose more than one!

Casablanca Grande - Nightly Rental 2 Bedrooms 2 Bath Sleeps 6

Pet-Friendly Casablanca Grande consists of the two neighboring vacation rentals "Casablanca" and "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 the perfect get-a-way vacation rental for those seeking a good time, but would like to stay a short distance from all the Duval Street craziness! With the two units, you can also be close to friends or family but still, have your own private space. Casablanca and Casablanca Too each sleeps 2 adults comfortably. You can also rent them separately, too!

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

If you are looking for a great location central to all that Key West has to offer, look no further! Situated in a lush garden setting, this location gets its name from the winter White House home of President Harry Truman, now a museum. "Seas the Day" is a newly updated first-floor condo that's located in the Shipyard section of the Truman Annex facing Southard Street.

Ashe House - Monthly Rental 3 Bedrooms 3.5 Bath Sleeps 6

This meticulously-kept, classic home shines with refinement and quality, with custom cabinetry throughout; a built-in wet bar just off the modern, fully-equipped kitchen, rare built-in fireplace for winter nights, a lovely, landscaped swimming pool and splendid tile work in the bathrooms. This is truly your perfect monthly home away from home!

Castaway Cove - Monthly Rental 2 Bedrooms 1.5 Bath Sleeps 4

Perhaps the most exciting part of "Castaway Cove" is the four complimentary kayaks available for your paddling pleasure with water access just steps away from your front door!. 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.

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. Located in a convenient spot in historic Old Town, this tropical house with pool house and half-bath is between the Southernmost Point and the Ernest Hemingway House. Completely restored, updated and uniquely furnished, you’ll find a cozy, turn-key-ready home away from home with everything you need for day-to-day relaxation.

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 front porch lies just off the master bedroom and is the perfect spot to start off your morning with a cup of coffee and a book or newspaper in your hand. 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.

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

My Happy Place is an exemplary renovation of a historic, Key West house. 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. 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.

Petunia Cottage - Monthly Rental 2 Bedrooms 1 Bath Sleeps 4

Petunia was recently renovated and updated so you’ll find brand new amenities, appliances and bed and bath linens. Top of the line appliances includes a washer and dryer and a delightful retro-yellow refrigerator to add a touch of whimsy. You’ll love entertaining family and friends in the expansive open kitchen and living areas, spilling onto the deck for fresh air and conversation. 

Steamplant 207 and 208 - Monthly Rental 3 Bedrooms 3.5 Bath Sleeps 8

These are Two Level, 5 Star Luxury Residences with breathtaking panoramic views of Key West. Guests love the private rooftop terrace with elevated pool, the parking garage, the private elevators for each residence, and that they're pet-friendly. Each 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.

The Pink House - Monthly Rental 2 Bedrooms 2.5 Bath Sleeps 5

Tropical light fills the inviting two-story home. The main floor’s contemporary open concept is perfect for entertaining. Upstairs, you will find two master suites: each with its own private porch. Indoor/outdoor living at its best is evident throughout the property. While away the hours on the classic double porches adorning the front and back. French doors lead to a large backyard deck, sparkling saline pool, and ambient waterfall. Mature tropical landscaping creates an island paradise in your own backyard.

Tropical Dream - Monthly Rental 4 Bedrooms 3.5 Bath Sleeps 8

This beautiful home is filled with amazing local artwork and has the tropical feel you seek when visiting Key West. All the amenities of the finest hotels; linens, bedding, flat screens, sauna, pool, private sunning deck, on-site parking are provided for your use. We guarantee that Tropical Dream will fulfill even the highest expectations. This amazing luxury vacation home is located on Millionaire’s Row in Historic Old Town Key West.

Come celebrate Key West living as birds of a feather flock to Key West. You can vacay and play, work and learn and just live like a local in our tropical and Caribbean destination. Start your Winter Getaway right on our website or with one of our fine-feathered Vacation Planners with all the information and recommendations you need to set up your winter nest!