Spend A Month In Key West

Our monthly luxury vacation rental homes in Key West are the perfect option for an extended stay in our tropical paradise. Immerse yourself in the warm and tropical paradise all month long and experience all that local living in Key West can offer.

How to Live like a Key West Local

Set your hearts aflutter on a bench under a gazebo and flamingle with Rhett and Scarlett, a breeding pair of pink flamingos at the conservatory. They’ll honk and spread their coral wings to welcome you. Join the tradition of taking your photos from the Southernmost Point, stroll along the Historic Key West Seaport and Harbor Walk, winding down to Mallory Square and the nightly sunset celebrations punctuated with lively and colorful street performers. 

What Are the Benefits of Spending a Month in Key West?

Make your stay an extended vacation so that you can unwind and experience the best of the Florida Keys! Discounts are often available for Key West monthly vacation rentals, especially in the off-season or if staying for multiple months. 

When Is the Best Time to Stay in Key West for a Month?

The best time to visit Key West is between March and May. Winter is the busiest, so the crowds taper off starting in spring and the weather continues to be reasonable and yet the weather is still blissful and in the 70s and 80s.  

When Is the Hottest Month in Key West?

August is usually the hottest month in Key West and it can be rainy, as well. 

When Is the Coldest in Key West?

December to February can be cooler in Key West, but the temperatures still hover in the 70s which is why winter is high season. 

Who Are Monthly Rentals Perfect For?

Our Key West monthly vacation rentals include utilities such as electricity, water, and propane, so they're perfect for everyone. Winter Snowbirds come for the winter, while families love the flexibility to stay, work and play. High-Speed Internet is a brand standard, so come for work, bring your project team, and keep up with your studies, too.

Why Would Someone Want to Stay in Key West for a Month?

There's no better way to soak up our Floribbean atmosphere, fresh seafood, sunshine, the arts, and our slower pace. 

Looking for the Perfect Key West Monthly Rental?

Explore our recommendations for the best Key West Monthly Vacation rentals and book to plan a month in paradise to enjoy all Key West local living has to offer.

Bahari House, Seaport- Monthly Rental - 2 Bedrooms 3 Bath Sleeps 6

Enjoy the beautiful outdoor area and covered, private covered patio with grill in the rear of the home. Both the front porch and second-story balcony of this pet-friendly home are great for people watching. 

Sea Vista - Monthly Rental - 3 Bedrooms 2 Bath Sleeps 7

Dreaming of putting your toes in the sand or sipping coffee on your dock? Then this is the vacation home for you! The lush backyard is gated and leads out to the warm Gulf of Mexico. Just steps from the water’s edge, this unique paradise has a dock for your shallow-draft fishing boat. There are several outdoor areas of enjoyment including a dining table, loungers, and covered porch with comfortable furnishings.

Browse our collection of monthly Key West vacation rentals to make your stay a breeze so that you can unwind and experience the best of the Florida Keys!