14 Key West Spots For The Summer Months

Historic Key West Vacation Rentals has 14 Key West spots available for the summer months. As temperatures rise this time of year, so does the fun and a month, or longer, by the sea is the best way to experience our Caribbean tropical paradise. Our vacation rental team lives and works in Key West. As locals, we can give great trip-planning recommendations, whether you're looking for the best restaurants, grocery stores, events, or quiet spots to spend time. We love introducing others to the wonders of Key West and our monthly boutique vacation rentals are the best places for your summer getaway experiences.

Through the numerous windows lie glimpses of greenery and sky that are a tableau 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 panels and white-painted walls combine into a balance of coziness and brightness, as well as varied backgrounds for displaying tasteful works of art. 

Tucked away behind the gate, you will find your slice of paradise in this hidden gem, Starfish. This spacious, bright 2 bed, 2 bath home, all on one level with a wrap-around porch for outdoor relaxation, is in the Southard Square community, which boasts a large shared pool and well-appointed pool house.

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

Cayo Limon features all the outdoor amenities you could ask for during your Key West vacation: a private, seasonally heated pool, a covered outdoor eating area, a large gas grill, an outdoor shower and plenty of poolside seating. The home also features a front porch and a balcony off the spare bedroom.

New decor and new photos coming soon. Southern Skies is the Great Old Town location you want for your family or friends getaway! A heated pool with a waterfall is private and luxurious. This home is just a 4-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.

The Steamplant is the second tallest building in Key West. Nowhere else can you step out of your secure, private elevator onto your one-of-a-kind Key West rooftop terrace 70 feet above the island. Enjoy a daily sunset dip in your private elevated rooftop pool. These opulent residences at the Steamplant offer unparalleled stunning views like no others on the island.

This restored historic home is located on a tiny one-way lane in Historic Old Town Key West, it has a private "saltwater" pool. Plenty of outdoor shaded seating for lunches on the lanai, Adirondack chairs for soaking up the sun, and a hammock are a pure delight! There is even a propane grill for your grilling your catch of the day.

Located in a convenient spot in historic Old Town, this 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.

Inn Cogneato is a newly renovated beautiful home located in one of the oldest parts of Historic Key West. Surrounded by a white picket fence, this home is perfect for a couple that plans on entertaining visiting guests or family during their stay. Beautiful wood floors throughout the home.

Historic Key West Vacation Rentals' monthly vacation rental properties are the perfect options for extended stays in our tropical paradise of Key West. We offer numerous luxury properties to make your stay hassle-free and filled with the best that Key West and the Florida Keys have to offer. Monthly rentals require 28-night minimums. Please keep this in mind when selecting your dates to be sure you meet this minimum night stay rule in order to bring up available options (due to strict city regulations, no exceptions may be made to the minimum stay). 

Monthly vacation rentals include utilities such as electric, water, and propane. Please read our rental policies for other rules and items specifically related to monthly vacation rentals. Reservations occurring during "Peak Season" require check-in dates on the 1st of the month and can only be rented in monthly increments. We're ready to welcome you to sunny Key West for the summer. Start your adventure right on our website or with our very sunny vacation planners. We look forward to having you as our guests this summer!