Monthly Rentals in the Florida Keys
Florida Keys monthly vacation rentals—defined as homes that rent for 28 days or more—offer the perfect opportunity to fully settle into island life. With an extended stay, you can slow down, explore at your own pace, and experience the Florida Keys beyond a typical vacation. From Key Largo to Key West, our homes are designed for comfort, convenience, and longer-term living.
Whether you're planning a seasonal escape, remote work stay, or simply looking to trade routine for sunshine, monthly rentals provide the space and flexibility to make the most of your time in the Keys.
Why Choose a Monthly Stay?
A longer stay allows you to experience the Florida Keys in a more meaningful way. Instead of fitting everything into a few days, you can spread out your plans, revisit favorite spots, and discover new ones along the way.
Enjoy boating, fishing, snorkeling, and dining at your own pace—or simply relax and enjoy the rhythm of island life without feeling rushed.
Live Like a Local
With a monthly stay, you’ll begin to experience the Keys like a local. Get to know the neighborhoods, find your favorite coffee spot or waterfront restaurant, and settle into a routine that blends relaxation with exploration.
Spend time in Islamorada for its laid-back charm, explore the variety of activities in Marathon, or take regular trips down to Key West for its energy and culture.
Comfort for Extended Living
Monthly vacation homes are designed to feel like a true home-away-from-home. With full kitchens, multiple bedrooms, comfortable living areas, and often dedicated workspaces, these homes support both relaxation and day-to-day living.
Many properties also feature outdoor living areas, pools, docks, and water access—making it easy to enjoy the Florida Keys lifestyle every day of your stay.
Ideal for Remote Work & Seasonal Stays
The Florida Keys are a popular destination for extended winter stays, remote work, and longer getaways. With reliable connectivity in many homes and inspiring surroundings, it’s easy to balance work and leisure.
Start your day with a walk by the water, take meetings with a view, and unwind each evening in a setting that feels far removed from the everyday.
A Different Kind of Getaway
There’s something special about having time. Time to relax, explore, and truly disconnect from routine. A monthly stay gives you that freedom—turning your vacation into an experience that feels both restorative and rewarding.
Book Your Florida Keys Monthly Stay
If you’re looking for a longer, more immersive escape, a monthly rental is the perfect fit. With the space to settle in and the time to enjoy it, these homes offer a deeper connection to the Florida Keys.
Browse our monthly vacation rentals and start planning your extended stay in the Keys.
78 properties available
🌴 TROPICAL BLISS ESCAPE – Key Largo Waterfront Getaway Escape to the laid-back charm of Key Largo, Florida, and discover the perfect blend of relaxation and adventure at this 3-bedroom, 2-bath waterfront retreat. With a private pool, guest dockage for boats up to 28 feet, and unbeatable access to both Florida Bay and the Atlantic Ocean, this
Your Waterfront Escape in the Heart of Islamorada Awaits! Welcome to your dream getaway in the Florida Keys—where turquoise waters, tropical breezes, and that unmistakable “island time” feeling set the tone for an unforgettable stay. Nestled right on the water in beautiful Islamorada, this spacious 3-bedroom home offers the perfec
Beautifully situated among the palms and right on a canal that leads out to open water, this three-bedroom home on Big Coppitt Key is the perfect Florida Keys escape for boating enthusiasts, anglers, and families and friends in search of waterfront relaxation. This single-story home provides a canal-front dock where you can park your boat, two kaya
This home is just perfect for your Keys getaway! The open floor plan and well-appointed kitchen will make your stay more than comfortable. French doors off the living room and primary bedroom offer beautiful views of the private pool and the lush tropical landscape in the enclosed yard. You will enjoy the private outdoor living area, including the
An exceptional stay awaits at this three-bedroom, two-bath condo. Inside, the suite is open and inviting, with a large flatscreen TV and comfy furnishings in the living room, plus a well-equipped kitchen with stainless steel appliances that include a French-door refrigerator. You'll have plenty of counter space to help you prepare your favorite
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions.* If Key West is on your itinerary, make this welcoming, conveniently located one-bedroom home yours and enjoy comfort and the benefit of being right in the heart of the island! You'll be in the cente
Prepare for true canal-front living at this home! Casual in nature and comfortable in every room, this home is ready with central air conditioning and enough seating for everyone. Cards and chips for late-night poker games are included for impromptu games, as well as a telescope for looking out at the sky over the ocean. Store the boat at the dock
Experience Key Largo at its finest when you book a stay at Afternoon Delight! Nestled alongside the water and equipped with a spectacular list of private amenities, your vacation will be shrouded in sunshine, lined by palms, and hugged by the sea breeze. Spend your days splashing in the heated pool, throwing cookouts for your family (thanks to the
Boasting a canal-front location, this two-bedroom home is a dream retreat on Summerland Key. Tie up a boat of up to 24 feet at the private dock. Cruise the canal with ease, travel mere minutes to prime fishing and diving locations, and come home to take a dip in the backyard plunge pool and sip tropical drinks in the festive tiki lounge. Kick back
Everything you need for a carefree Florida Keys escape is right at your fingertips in this laid-back bungalow. Boasting direct canal access by way of a private dock, this waterfront retreat also features a tropical outdoor area and recent home upgrades including an all-new kitchen and primary bathroom. A fully screened-in lanai offers a breezy perc
Escape to Your Oceanfront Paradise in Ramrod Key, FL Discover the perfect blend of relaxation and adventure at this vibrant oceanfront retreat in beautiful Ramrod Key! Designed for families, friends, and thrill-seekers alike—plus it’s dog-friendly, so your four-legged family members are welcome too! Wake up just steps from the turquoise
The ideal location of this super-comfortable corner property makes it the perfect blend of convenience, tranquility, and tropical Key West scenery. Sit back and relax as you sip cocktails on the balcony, prepare a light meal in the newly renovated kitchen, and unwind in front of the living room smart TV after a day at neighboring Fort Zachary Beach
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