Key West Waterfront Rentals

Immerse yourself in the tranquil beauty of Key West with waterfront vacation rentals from Last Key Realty. Our carefully selected properties provide a serene waterfront retreat, allowing you to experience the peaceful ambiance of the Keys right at your doorstep.

At Last Key Realty, we specialize in offering waterfront rentals that encapsulate the unique charm and natural beauty of Key West. Each rental is designed to provide a comfortable and memorable stay, with the calming waters as your backdrop.

Our commitment goes beyond just providing a rental space; it's about ensuring a seamless and enjoyable experience as you explore the serene waters and vibrant culture of Key West. Reach out to Last Key Realty for your waterfront vacation rental needs in Key West. Your tranquil waterfront escape awaits!


Properties Available 28 properties available
SUNDRENCHED REFLECTIONS is very close to Old Town, with access to all the attractions that Key West has to offer. Yet, you'll be in your own world with a large sundrenched balcony overlooking Florida Bay and the Gulf of Mexico beyond. THE PRIVATE GATED COMMUNITY... Sunset Marina is a gated community located on Stock Island, right off the entrance t
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)
Sundrenched Reflections
Condo
$175.00 - $487.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (10)
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
$175.00 - $551.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (4)
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
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)
Baypoint Oasis
Private Home Pet Friendly
$255.00 - $949.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (6)
OCEANFRONT OASIS is a boater’s paradise featuring incredible views, modern decor, and dockage that can handle a mini yacht. This five-bedroom home provides the ultimate escape for those needing a break from their fast-paced everyday life. Imagine yourself relaxing in the pool, soaking up some sun as you gaze across the endless ocean. When it’s tim
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)
Oceanfront Oasis
Private Home Pet Friendly
$400.00 - $1,228.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 12 guests
Looking to land at the perfect vacation rental to explore Key West and the Lower Keys? Then look no further than THE LARK’S LANDING. Found on the top floor of Sunrise Suites, THE LARK’S LANDING features all new furniture and TVs, a private balcony, Two Bedroom Suites, a comfortable living room, and a full kitchen. With a location near the entrance
The Lark's Landing
Condo
$210.00 - $798.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (48)
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
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Turtle Cove Views
Cottage Pet Friendly
$222.00 - $712.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (151)
The vacation opportunity of a lifetime awaits at CASSIE’S PARADISE. A secluded oceanfront experience, this breathtaking home sits on over half an acre and is less than 20 miles from Key West. The 4,300 sq ft interior affords your group plenty of room to spread out. The real showstopper of this home is the backyard - complete with 120 feet of privat
Cassie's Paradise
Estate Pet Friendly
$3,500.00 - $6,553.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (6)
SHANG-RI-LA is a term for a utopia designed for life-long learning, happiness and fulfillment. There is no better place to find your happiness and fulfillment than a waterfront oasis on a little island at the farthest Southern tip of the US. This water view condo has been meticulously furnished with a modern coastal feel, with a front row seat to y
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Shang-Ri-La
Condo
$220.00 - $1,404.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (329)
GULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of GULFSIDE VISTAS, and two spacious balconies as well.Compliance with Truman Annex Community Rules & Regulations is expected of all
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2026 Changes 2026 Changes
2026 Changes
Starting January 1, 2026 every home in Truman Annex (including this one) will become a monthly-only rental. This is due to a new City Ordinance, so it will need to be rented for a minimum of 29 nights. Call 305-292-6266 for further information.
Gulfside Vistas
Condo
$430.00 - $1,550.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (264)
For a month in Key West it is ideal to harness the comforts of new construction similar to the luxuries of your own home, but keeping the true spirit of Old Town Key West and the magical surprises around every corner. This brand newly constructed home, located a stone's throw from the Southernmost Point, also backs up to the famous Butterfly Museum
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)
Dance of the Butterflies
Private Home Pet Friendly
$237.00 - $755.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (6)
SUNSET POINT has everything you could want in a vacation home: it is close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world at SUNSET POINT with a very large balcony overlooking the Florida Bay and the Gulf of Mexico beyond.THE PRIVATE GATED COMMUNITY...Sunset Marina is a gated communit
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)
Sunset Point
Condo
$137.00 - $487.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (23)
COSTA VIDA is a freshly built, elevated Florida Keys home that embraces life on the coast and provides an ideal setting for those looking to enjoy an easygoing vacation. Located less than 25 miles from Key West, this beautiful waterfront property is situated oceanside on a deep-water canal, which makes getting out on the water a breeze. When you’re
Hot HOT 53
New Property New Property
New Property
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)
Costa Vida
Private Home Pet Friendly
$216.00 - $945.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (3)

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