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
Live Like a Local in the Heart of Key West! Welcome to your next luscious Vacay getaway—where history, culture, and island living come together just steps from your door! Located only 500 feet from the iconic Hemingway House and the Key West Lighthouse, and just two blocks from lively Duval Street, this centrally located cottage puts you with
License number: 25,230-1322,99. Welcome to Paradise in Key Largo – your private waterfront oasis just one mile from the breathtaking John Pennekamp Coral Reef State Park! Whether you're looking for outdoor adventures, a family retreat, or simply peace and quiet in the Florida Keys, this spacious and beautifully appointed home offers the p
A sparkling pool, sweeping ocean views, and enviable proximity to Key West fun make The Mermaid Manor a dream island retreat. Rent a boat and glide through the waters off the coast, or launch the provided kayak from the dock and paddle the channels winding through the outlying islands. Explore the island on bikes, or book snorkeling, charter fishin
This remodeled home is set right on the beach, and is equipped for guests to have a lot of fun on the beach! Towels, a beach umbrella, and four beach chairs are included for guest use on the private sandy beach. Shower off the sand before coming inside the covered deck and grabbing something delicious cooking on the private gas grill. Guests can co
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
Prime Key West Location Escape to laid-back island living in this inviting Key West retreat, where tropical beauty and everyday comfort come together seamlessly. Tucked away in a quiet, greenery-filled neighborhood, this single-story home offers a peaceful setting while keeping you close to everything that makes Key West unforgettable. Step outside
*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. This home is perfect for anyone coming to the Keys to spend time on the water. The two-story home sits on the widest canal in Hammer Point that leads to Florida Bay and has its own private dock capable
An escape to the Keys is never a bad idea, so treat yourself to a stylish getaway and kick back in bliss here at Coral Delight! Sitting right on the coast, you will have no delay in getting your fill of sweet sunshine, sandy toes, and sun-kissed skin. As soon as you step inside, you will be greeted by the tropical decor, plush furnishings, and plen
Playful pops of color, resort amenities, and a prime location await you at this marvelous vacation home! Whether you're out enjoying the sand and waves, taking a refreshing splash in a shimmering pool, or enjoying the charming comforts of your getaway, there is nothing short of possibilities and wonder here!Upon entering, you'll be met with an invi
Find your own little piece of paradise at Tarpon Watch, a waterfront escape offering gorgeous views of the Gulf of Mexico, plenty of room for you and your loved ones to relax, and an ideal location close to Key West's most beloved attractions. At the end of each beautiful day, mix up a favorite beverage at the wet bar, step out onto the large b
Just a short walk from a lovely community park, this friendly home has plenty of room for guests to come in and relax. Unwind in central air conditioning inside or enjoy a beverage out on the private, furnished patio. If you're coming back from the ocean, the private washer/dryer will take care of the swimsuits and towels while you relax. The s
🌴 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
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