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.

156 properties available

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

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

All year long you dream of a getaway to capture that feeling of Key West's ENDLESS SUMMER - carefree days spent tooling around Old Town on bicycles or wandering the island streets in flip flops with the sun warming your shoulders. No plans, nowhere to be, no deadlines - only a to-do list of making memories with your family and friends and possibly

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Endless Summer

Private Home

$675^.00 - $4,052^.00 / per night

If you’re looking for the perfect place to spend your month in Key West, look no further than KOKOMO & TORTUGA at Seaport Inn! KOKOMO & TORTUGA is the combination of two ground level units at the historic Seaport Inn that are right across the hall from each other. This is the perfect arrangement for a pair of couples or a family looking to

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)

Kokomo & Tortuga

Condo

$333^.00 - $765^.00 / per night

A trip to Key West is like a breath of fresh air! The sounds of rustling palm trees, the scent of fragrant flowers and the smell of salt air are the rejuvenation that only the tropics can provide. This home is a breath of Key West fresh air, or BRISA FRESCA, a timeless, beach-inspired home that seems to be straight out of the pages of Coastal Livin

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2026 Changes

Brisa Fresca

Private Home

$860^.00 - $2,218^.00 / per night

Finally, a large vacation home where every member of the family will be happy. From the vaulted living room with three couches and a giant 60-inch TV, to the kitchen large enough for a whole team of chefs to prepare dinner, CASA OLIVIANA has it all.THE LIVING AREA...The aforementioned living room is truly big enough for the whole family. The only d

Casa Oliviana

Private Home

$345^.00 - $1,264^.00 / per night

If the allure of the Caribbean is calling you but you don’t want to pull out your passport, a month at the ANTIGUA SUITE at the Seaport Inn does just the trick! This suite is perched on the second floor of the Seaport Inn and just a short walk to all Old Town has to offer. Paired with Last Key Realty’s Five-Star Guest Services and Complimentary Con

Monthly Rental

Antigua Suite

Condo

$138^.00 - $486^.00 / per night

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

Coastline Comfort

Condo

$200^.00 - $865^.00 / per night

There’s no better way to escape the hustle and bustle of reality than by sneaking off to Key West for a taste of the island life. ELEGANT ESCAPE offers first-class accommodations in a beautiful tropical setting. From the open layout and soaring ceilings of the main house to the enticing private pool and unique guest cottage, ELEGANT ESCAPE has ever

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2026 Changes

Elegant Escape

Private Home

$850^.00 - $2,992^.00 / per night

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

Look for the coral pink “Sugarpoppy” door on this quintessential conch cottage and you’ll know you’ve found a special vacation home. This cozy little gem is located on a quiet one-way street just a block off of Duval. In addition to the superb location, this one-story home also offers top-notch amenities. With a dreamy front porch, a private heate

Monthly Rental

Sugarpoppy Cottage

Private Home

$200^.00 - $715^.00 / per night

COLORS OF THE KEYS is a bright and vibrant townhome that embodies Key West’s colorful & tropical spirit. Located within Truman Annex, Key West's most exclusive gated community, this home is within walking distance of all that Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to a prime location, COLORS OF THE

2026 Changes

Colors of the Keys

Townhome

$350^.00 - $1,220^.00 / per night

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

2026 Changes

Green Turtle Cottage

Private Home

$415^.00 - $1,411^.00 / per night

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