Lower Keys Vacation Rentals: Your Private Island Escape

The Lower Florida Keys offer a different pace of life. Away from the constant movement of the city, these islands provide a quiet setting for those who value space, water access, and natural beauty. At Last Key Realty, we manage a selection of homes that allow you to experience this region like a local.

Discover the Seclusion of the Lower Florida Keys

Choosing a rental in the Lower Keys means trading crowds for mangroves and traffic for tide charts. This area is defined by its vast wildlife refuges and open water views. Whether you are fishing off a private dock or watching the sunrise from a screened-in porch, the focus here is on the outdoors. Our properties are located in quiet residential areas, giving you a sense of privacy that is hard to find in more developed tourist spots.

Luxury Amenities for Your Stay

We believe a vacation home should function better than your own. Our Lower Keys rentals feature:

  • Water Access: Many homes include private docks suitable for boats of various sizes.
  • Private Pools: Cool off in your own backyard after a day on the water.
  • Chef’s Kitchens: Fully equipped spaces for preparing the day's fresh catch.
  • Pet-Friendly Options: Bring the whole family along to enjoy the island life.

Luxury Lower Keys vacation rental featuring a private waterfront pool and spa with ocean views at sunset.
A private wooden dock with turquoise kayaks and boats at a waterfront vacation rental in the Lower Florida Keys.

Explore the Islands

The Lower Keys are a collection of unique neighborhoods, each with its own character.

  • Big Pine Key: Home to the Key Deer National Wildlife Refuge and the famous No Name Pub.
  • Cudjoe Key: A boater’s dream with quick access to both the Atlantic and the Gulf.
  • Summerland Key: Known for its private airstrip and wide canals.
  • Bay Point: A hidden gem just minutes away from the amenities of Key West.

The Last Key Realty Difference

Booking with us means more than just receiving a key code. We provide a full-service experience. From the moment you arrive, our guest services team is available to assist with local recommendations, grocery delivery, or bike rentals. We live here, we work here, and we take pride in maintaining the highest standards for our homes.

Ready to find your quiet corner of the Florida Keys? Browse our available listings below or contact our local team to discuss your specific needs. We help you find the right home for your timeline and budget.


Properties Available 7 properties available
Formerly known as Playland in Paradise, the ultimate Keys vacation awaits you at BAYPOINT OASIS! This spacious waterfront property is perfect for large groups, featuring an open floor plan, six bedrooms, including three master suites, and expansive outdoor space. BAYPOINT OASIS offers every amenity you could ask for in a vacation home… and then som
Monthly Rental Monthly Rental
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A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Baypoint Oasis
Private Home Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (6)
Escape the “changing tides” of your day-to-day routine by spending a month in the Keys. MARINER’S HIDDEN HAVEN provides an ideal island setting for re-centering your compass by way of your own private waterfront retreat. Picture mornings sipping coffee on the dock, lazy days by the pool, and beautiful sunsets on your boat. The home’s open layout an
Monthly Rental Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Mariner's Hidden Haven
Private Home Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (5)
TURTLE COVE VIEWS is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expansive open water views from inside the home through the large windows or from your covered porch, with outdoor dining. The private 35-foot boat slip offers easy access to the beautiful waters of the Florida Keys and the home com
Hot HOT 31
Turtle Cove Views
Cottage Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (177)
TIDEWATER VIEWS is a cozy 820 square foot cottage that has everything you want for the perfect tropical vacation: open water views from a covered porch, a private 35-foot boat slip, kayaks, bikes and access to the wonderful amenities at Venture Out, a residential community with a heated 80-foot pool with large Jacuzzi and Kiddie Pool, tennis courts
Hot HOT 35
Tidewater Views
Cottage Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (330)
Life in the Florida Keys is all about spending time outdoors, indulging in the things you love with the ones you love; and BLUE HORIZON is the perfect vacation home to experience Keys living for yourself. Whether your ideal day is floating around the large pool with a cold drink in hand, cruising the waters of the Lower Keys in your boat, or gather
Monthly Rental Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Blue Horizon
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (1)
From the moment you arrive to this spectacular Florida Keys home, you will feel all your stresses and worries simply melt away. CAREFREE ON CUDJOE is an expansive waterfront property that evokes the easy-going nature of Keys living and provides an ideal setting for those looking to enjoy a ‘carefree’ vacation. There will certainly not be a shortage
Monthly Rental Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Carefree on Cudjoe
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating Rating Rating Rating Rating 5 (4)
As if a vacation to the Florida Keys wasn’t memorable enough, the million-dollar views from INFINITE HORIZONS are ones you’ll never forget. Located about 10 minutes north of Key West on Big Coppitt Key, INFINITE HORIZONS sits on an oversized, open water lot with a private pool and beach placed against the stunning backdrop of the gorgeous Gulf of M
Monthly Rental Monthly Rental
Monthly Rental
A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)
Infinite Horizons
Private Home Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (5)

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Frequently Asked Questions


Which islands make up the Lower Florida Keys?

The Lower Keys encompass the stretch of islands from Big Pine Key down to Stock Island. This area includes popular destinations such as Summerland Key, Cudjoe Key, Sugarloaf Key, and Little Torch Key, known for their quiet residential character and natural surroundings.

Is it better to stay in the Lower Keys or Key West?

The choice depends on your desired pace. Key West is a compact island city known for its social scene and historic sites. The Lower Keys offer a secluded alternative with more space and a focus on water-based activities like fishing and kayaking, while remaining close enough to Key West for day trips.

Do Lower Keys vacation rentals include private boat docks?

Many properties in our inventory feature private deep-water docks or canal access. These homes allow you to keep your vessel on-site and provide quick access to both the Atlantic Ocean and the Gulf of Mexico for fishing or snorkeling at Looe Key.

What are the best beaches near the Lower Keys?

The most famous beach in this region is found at Bahia Honda State Park. It offers some of the best sand and clearest swimming waters in the entire island chain, providing a traditional beach experience amidst the region's mangroves and rocky edges.

Do I need a car when staying in the Lower Keys?

Yes. Unlike Key West, where you can easily get around on a bicycle, the Lower Keys are spread out. You will need a vehicle to access grocery stores, local restaurants, and the various state parks located along the Overseas Highway.

What is the best time of year to visit?

High season runs from December through April, offering the most comfortable weather. The shoulder months of May and June often provide a balance of warm temperatures and fewer crowds.