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.

155 properties available

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 - $845^.00 / per night

If you dream of waking up to expansive water views and island breezes, and walking out your front door right onto the streets of Old Town Key West in the center of it all - PROMENADE TO PARADISE is everything you are looking for. With a spacious layout, relaxed island-style furnishings, a semi-private gated pool, and three private balconies all you

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.

Promenade to Paradise

Condo

$415^.00 - $1,497^.00 / per night

For many, the artistic island culture of Key West is an intricate piece of its magic. THE ARTISTS' MUSE is an ode to that notion. This home, with its rich history of artists living in residence or visiting as guests, has been recently redesigned to celebrate art, culture, and the upscale island life. A spacious main living and dining area, a brand

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)

The Artists' Muse

Private Home

$300^.00 - $990^.00 / per night

Perched above the sights and sounds of Duval Street, sits TOP OF OLD TOWN, a recently renovated 2-bedroom private home, located within a secluded community in the heart of Old Town. This hidden gem offers a spacious interior, multiple outdoor spaces, and access to the community pool. Combined with Last Key Realty’s Five Star Guest Services & Co

Top of Old Town

Condo

$350^.00 - $1,676^.00 / per night

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

$3,500^.00 - $6,106^.00 / per night

Get ready to reel in Last Key Realty’s newest vacation home! THE WICKED TUNA is a classic Key West home located in one of the most desirable areas of Old Town. This tastefully restored home features a historic appearance and charm, while offering all the modern conveniences one could desire. Located just down the street from the historic seaport, y

Monthly Rental

The Wicked Tuna

Private Home

$225^.00 - $682^.00 / per night

2 bedrooms

2 baths

4 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

New Property

Monthly Rental

Sunflower Melodies

Private Home

$222^.00 - $765^.00 / per night

3 bedrooms

2 baths

6 guests

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

2026 Changes

Elegant Escape

Private Home

$850^.00 - $2,995^.00 / per night

When the ‘Welcome to Key West’ sign hits your eye, like a big pizza pie, THAT’S AMORE! If you’ve ever visited Key West, you know how easy it is to fall in love with the charm of this little island. It’s even easier to fall in love when staying in a lavishly decorated and furnished, fully stocked, historic home in the heart of Old Town, and THAT’S A

Monthly Rental

That's Amore!

Private Home

$333^.00 - $1,125^.00 / per night

It doesn't get any 'sweeter' than vacationing with a large group of your closest friends and family in America's Paradise. As a combination of two side-by-side private homes, SWEET AMERICANA not only offers plenty of comfortable accommodations for the whole crew but is an extremely rare find in the center of Old Town Key West. Located at the end of

Sweet Americana

Compound

$1,300^.00 - $5,825^.00 / per night

ISLAND BLISS is a classic Old Town Key West home, complete with delicate gingerbread accents, a classic Southern front porch with rocking chairs, and lush, tropical foliage tastefully surrounding the property. This beautiful, historic two-story home has been lovingly cared for and restored with a mix of modern touches and traditional Key West influ

Monthly Rental

Island Bliss

Private Home

$225^.00 - $760^.00 / per night

3 bedrooms

2 baths

8 guests

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 - $475^.00 / per night

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