Key West Vacation Rentals

Are you looking for Key West rentals that are both luxurious and convenient? Look no further than Last Key Realty! Our properties are strategically located across Key West's most coveted areas, including the historic charm of Old Town, the serene beaches at 1800 Atlantic, the exclusive Truman Annex, and the picturesque Sunset Marina. Plus, we offer rentals near Duval Street, the lively heart of Key West.

Our rentals here in Key West cater to your needs, whether you're planning a quick getaway or an extended stay. Available for nightly, weekly, or monthly stays, our properties offer a range of premium amenities. From fully equipped kitchens for culinary enthusiasts to private pools and outdoor dining spaces for those who love to entertain, we have everything you need to make your stay comfortable.

And for those who can't bear to leave their furry friends behind, our pet-friendly options ensure that no family member misses out on the fun in Key West!

Would you prefer a condo setting? Our vacation condos feature luxurious amenities, including communal pools, spas, and tennis courts.

When planning your stay in Key West, remember that regulations require a transient rental license for short-term stays. As these permits are limited, short-term rental rates may be higher than monthly rentals.

To find the perfect fit for your stay, simply use our user-friendly search bar. Input your travel dates, and our system will show you the most suitable options, including flexible rate options, to ensure you find your ideal Key West rental. At Last Key Realty, we're dedicated to making your stay in Key West genuinely memorable. Don't hesitate to contact our property managers for any help or if you have questions about your booking.


Properties Available 154 properties available
OCTOPUS'S GARDEN has been whimsically decorated with furnishings that reflect the laid-back, quirky island life style of Key West. Located in the gated community of Coral Hammock, you will be just down the street from the famous Hogfish Bar & Grill, Roostica Pizzeria, Hurricane Hole Marina & Restaurant and Chico's Cantina. The Key West Golf
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Octopus's Garden
Private Home
$250.00 - $1,112.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (389)
When your vacation is set around your experiences on the water, where you choose to spend your time on land should be convenient and comfortable. Whether it be a day at the sandbar… reeling in a big catch… kayaking through the mangroves - COASTLINE COMFORT is the perfect place to retire after an epic day on the water around Key West. Located in th
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Coastline Comfort
Condo
$200.00 - $873.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (163)
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 - $488.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (10)
Located on Solares Hill in the heart of Old Town, HAVANA HOUSE captures the simple elegance of Key West's Conch homes of the fifties, when it was still possible to sail to Havana.THE LIVING AREA...The living room of HAVANA HOUSE has a vaulted ceiling, with walls of Dade County Pine. There is a large flat screen TV and comfortable seating for everyo
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)
Havana House
Private Home Pet Friendly
$225.00 - $815.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (51)
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
$250.00 - $757.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (6)
Imagine a home with floor-to-ceiling panoramic views of the Atlantic Ocean from every room. WINDSWEPT PALMS has been thoughtfully decorated and furnished. The modern, upscale furniture is complemented with splashes of color throughout the home. The balcony wraps 270 degrees around the condo, with seating for everyone in your group. WINDSWEPT PALMS
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Windswept Palms
Condo
$445.00 - $2,431.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (206)
A home designed to impress the most discerning travelers, LAYOVER IN PARADISE is an oasis of comfort sure to meet the expectations of those accustomed to first class treatment. LAYOVER IN PARADISE is a newly constructed private home in the Casa Marina neighborhood that offers three spacious private suites, each with a large en-suite bathroom - and
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)
Layover In Paradise
Private Home Pet Friendly
$333.00 - $895.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (6)
This freshly renovated condo is located at 1800 Atlantic Blvd on the beach, just steps from the Atlantic Ocean and sand in your toes. Enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling sliding glass doors, or while sitting on your private balcony surrounded by the palm tree tops. DRIFTWOOD DREAMS is locate
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)
Driftwood Dreams
Condo
$150.00 - $430.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (10)
With a sense of gracious royalty, QUEEN OF LOUISA will treat you to an unforgettable stay in Key West. Her ideal location, modern interior, private pool and thoughtful touches throughout will ensure you and your group have everything you could want in a vacation rental. QUEEN OF LOUISA offers cozy bedrooms, a fully stocked kitchen and a fantastic o
Queen of Louisa
Private Home Pet Friendly
$625.00 - $3,161.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 5 (86)
GREEN TURTLE COTTAGE will help you come out of your shell and slow down to a turtle’s pace. This 2 bedroom, 2.5 bathroom home is located in the highly sought after Truman Annex neighborhood, putting it within walking distance to Old Town's most treasured restaurants and attractions. GREEN TURTLE COTTAGE is a relaxed home that features coastal, beac
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Green Turtle Cottage
Private Home
$415.00 - $1,410.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
SUNFLOWER MELODIES captures the feeling of a childhood summer, like your bare feet on freshly cut grass, the summer sun gently kissing your skin or the sweet, subtle scent of a field of wildflowers in bloom. A month in Key West is defined by a simpler way of life, with low stress, high fun, and heaps of relaxation - which SUNFLOWER MELODIES provide
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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)
Sunflower Melodies
Private Home Pet Friendly
$222.00 - $765.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests

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