Live Like A Key West Local For A Month

life like a local
by Historic Key West Vacation Rentals

Live like a Key West local for a month or longer so you can immerse yourself in our warm and tropical paradise and experience all that local living in Key West can offer. Discounts are often available for Key West monthly vacation rentals, especially in the off-season or if staying for multiple months. Our Key West Monthly vacation rentals include utilities such as electricity, water, and propane. Here we've prepared a list of family-friendly opportunities and activities that will have you in flip flops and floribbean wear in no time. 

How to Spend a Month in Key West


Take a Bike Ride Along the Waterfront

From our famous Historic District to the picturesque waterfront, bike riding is our favorite way to experience Key West. Our southernmost paradise measures about four miles by two and it’s flat, so you’ll have an easy go of it. Cars are few and speed limits are low, so set your pace to enjoy our natural paradise, its cool architecture, hip, and happy hangouts, and the local characters you’ll meet along the way. 


Spend the Day Kayaking or Paddleboarding

Enter into a lush marine world of mangrove islands and patch reefs and sponge gardens. Kayak through our various ecosystems to meet a variety of tropical birds, rays, sport fish, and the like. Paddle across the Gulf of Mexico or explore our creeks and shallow water. 


Explore the Dry Tortugas and Fort Jefferson

Named for the large population of sea turtles that live around the island, the Dry Tortugas are a group of islands located about 67 miles from the end of the Keys. It’s a Bucket List paradise for secluded, exotic beaches, birding, snorkeling, and more.


Go for Dive

What better way to enjoy our Key West sunshine than to dive right in? From snorkeling and parasailing to jetting around on WaveRunners. Add a full-day catamaran excursion and make a day of it with full breakfast and buffet options as dolphins frolic alongside. 


Spend the Day Charter Fishing

From a small group on a small boat to an all-day marine adventure, day or night, with a large group, Key West is where every angler wants to be. Choose from deep sea fishing, light tackle offshore fishing, flats fishing, or backcountry fishing. Adventurers, naturalists, and sportsmen alike all reel in their most fantastic fish tales in Key West.


Explore Old Town Key West By Foot

Enjoy even more of our paradise by parking your car and just enjoying the sights, sounds, and aromas of our walkable Old Town. Experience Mallory Square, Duval Street, and Whitehead Street. Stretch your legs with a good pair of walking shoes. No worries. Key West Trolley will let you hop on and off as needed.


Book the Perfect Home for the Month

To make your transition to full local Conch Republic resident, you'll need a proper Key West house.  Explore our collection of luxury Key West Monthly rentals ranging from intimate solo travelers and couple hideaways to cottages and larger homes. Our special Key West compound properties are perfect for group vacations, whether you're traveling with your entire family or a group of friends. We have a selection of Key West Monthly Vacation Rentals with private pools and access to community pools. There's nothing like relaxing next to a fabulous pool while after a long day of exploring.

Current Key West Monthly Rental Specials

Bahari House has a special spring vacation rate for April 2023. Enjoy the beautiful outdoor area and covered, private covered patio with grill. Both the front porch and second story balcony of this pet-friendly home are great for people watching. You can walk to the harbor, too!

Azur Palm is offering a monthly vacation special rate for May and/or June 2023. There are tennis courts, a gym, two shared grill areas and two shared, heated pools. The beach is just a few yards away. You'll be near the White Street Pier, Higg’s Memorial Beach Park, and the Key West Nature Preserve. Within walking or biking distance of shops, restaurants, and the delights on Duval Street.

Ashe House is all set to debut its new renovation that includes lush landscaping for privacy around the pool with lounge chairs and gas grill. An outdoor shower completes the Key West vibe! You'll live like a local in Old Town, north of Truman Avenue in a quiet residential area within walking or biking distance of several shops, galleries, and restaurants.

Pet-friendly Villa Azul also just announced special monthly rates for May and June 2023. The main house is a two-story historic cottage with Brazilian cherry hardwood floors. Behind the main house is a private poolside guest cottage with a Queen bed, ensuite bathroom and a delightful outdoor shower. The loggia, with teak bench, is the perfect place to enjoy your afternoon cocktail while cooking on the gas BBQ. Grill the day's catch of fresh fish!

Bring Your Dog

Traveling to Key West with a dog is easy as many of our rentals are very dog-friendly. Furry friends are even allowed in some bars and restaurants on our island. There are also several dog parks and even a dog beach! 

Start Planning Your Next Key West Vacation

Our Key West rental homes are happy to serve as your home away from home, so browse through our assortment of Monthly Rentals in Key West to find the perfect home base for your next getaway to the Florida Keys.  Can't decide? No worries. Our local vacation planners are always happy to help you make your selection and would love to help assist in planning your stay.