14 Reasons For A Month Long Vacation To Key West

Key West temperatures range from highs around 85 degrees to lows around 76 degrees. Sounds perfect? You bet and it's why the Conch Republic is so popular with month-long vacationers. Key West may be small, but we have several neighborhoods as unique and special as you'd expect for such a quirky and exotic paradise. Our collection of premier monthly vacation rentals is just as varied. Our skilled vacation planners are happy to help you select just the right one for your stays of a month or longer and one that's closest to your favorite beach!

Bahama Getaway

Monthly Rental | 4 Bedrooms, 3 Bath, Sleeps 8

Bahama Getaway consists of three buildings. They are all single story. There's a main house with three bedrooms, each room has a full-size bed. It has two full baths, a kitchen, a dining area, and a living room. There's also a large guest cottage with a bathroom, a mini-refrigerator, a coffee maker, and a microwave. A laundry cottage with a washing machine and clothes dryer completes this monthly rental.

Beachfront Breeze

Monthly Rental | 2 Bedrooms, 2 Bath, Sleeps 4

Few rentals have the luxury of a water view and beach access on our island. Just minutes from downtown Key West, this condo is located on the quieter side of the island with nothing around you but the beautiful white sand of world-famous Smathers Beach.

Coconut Cottage

Monthly Rental | 2 Bedrooms, 2 Bath, Sleeps 4

Guests love this a bright, cute and sunny condo in the gated Sunset Marina Condominium Complex community. It's tucked away on Stock Island between the Key West Golf Course and the beautiful waters of the Caribbean Sea.

Island Days

Monthly Rental | 3 Bedrooms, 3 Bath, Sleeps 8

With a large heated resort-style pool and Tiki Hut right outside your French doors, this rental has it all. It features lush landscaping and off-street parking steps to your door to complete the resort feel. This private townhouse is located in the gated Coral Hammock community just minutes from Old Town Key West.

My Happy Place

Monthly Rental | 2 Bedrooms, 2 Bath, Sleeps 4

This Key West House retains its original character and wisdom, but with up-to-date comfort and high-quality interior design. Built in the shotgun style, this home’s front door enters a hallway that extends to the back of the house. This architectural device both harmonizes indoor and outdoor space and ventilates the rooms, as was necessitated in days before air-conditioning.

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. Petunia has a sister, Poppy. We mention that because you might be inclined to take both homes for a family retreat. Both are superbly private and quiet, but why not consider taking them both and sharing a Key West season with the family?

Poppy Cottage

Monthly Rental | 1 Bedroom, 1 Bath, Sleeps 2

Poppy is located in a quiet Old Town neighborhood, just steps from The Meadows and the White Street Art District. It’s an easy walk or bike ride to the entertainment, restaurants, and shopping along Duval Street, and close enough to the Historic Seaport to stroll for dinner and a drink at sunset. Solo guests and couples love its intimate feel and it pairs perfectly with Petunia Cottage for a wonderful family getaway!

Southern Skies

Monthly Rental | 3 Bedrooms, 2.5 Bath, Sleeps 6

This is the Great Old Town location you want for your family or friends getaway! The heated pool with waterfall is private and luxurious. This home is just a four-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 Units 207, 208, and 211

Monthly Rentals 3 Bedrooms, 3.5 Bath, Sleeps 8

These are two-level, 5 Star luxury residences with breathtaking panoramic views of Key West. Each includes a private rooftop terrace with an elevated pool, parking garage, private elevators for each unit and they're pet friendly!

The Pink House

Monthly Rental | 2 Bedrooms, 2.5 Bath, Sleeps 5

Tropical light fills this inviting two-story home. The main floor’s contemporary open concept is perfect for entertaining. This is indoor/outdoor living at its best. While away the hours on the classic double porches adorning the front and back.

Villa Azul

Monthly Rental | 3 Bedrooms, 3 Bath, Sleeps 6

Villa Azul consists of two separate buildings; the main house and a separate pool house! The main house is a two-story historic cottage with Brazilian cherry hardwood floors. Beyond the French doors awaits the private heated pool with a tranquil waterfall, lush tropical gardens, and loggia with purple passion vines.

Plan Your Vacation to Key West

These are just 14 of our premier monthly vacation rentals. We also offer nightly and weekly rentals. Key West continues to be a much sought after vacation destination. When the winter crowds leave, you'll enjoy weather that's warm and pleasant. Start your search from our Key West vacation rentals or with one of our vacation planners today!