Book Direct & Save

At Last Key Realty, located in Key West, we work directly with homeowners to ensure that you receive the best possible rental rate on your vacation rental property! Search our wide inventory of Key West Home Rentals, Condo Rentals, Rentals With Pools, Luxury Rentals, and more!

WHAT ARE THE BENEFITS?

When you book directly through a Vacation Rental Management Company like Seaside Vacations, you not only get the best rate possible, but you also receive local assistance before and during your vacation! Cut out the middle man and book directly at the source. There are a lot of vacation rentals located in Key West, FL, and we can guarantee all of the vacation rentals in our program are well managed and properly maintained. With a variety of amenities to select from, you are sure to find something for every member of your vacation crew.

NO ADDITIONAL FEES

Online Travel Agencies (OTA's) like VRBO, Tripadvisor, Airbnb and Expedia now charge you a service fee to book on their sites. Fees up to 20% are added to the cost of your reservation when you book through a third-party site.

LOCAL SERVICE & EXPERTISE

To book at the lowest possible rate and get local knowledge and expertise, reserve online today or call us at 305.292.6266. Our staff is here to provide you with the highest level of customer service. We look forward to having you stay with us soon!

144 properties available

The vacation opportunity of a lifetime awaits at GRAND KEY OASIS. This breathtaking one-of-a-kind property is the epitome of luxurious island living, featuring two separate homes connected by a covered pavilion that overlooks the exceptional backyard and resort-style private pool. The interior design of this compound will leave you marveling at the

Grand Key Oasis

Compound

$1,111^.00 - $6,040^.00 / per night

When you think of Key West, you think of spending relaxing days with your toes in the sand under the palm trees, and fun-filled nights walking through the Streets of Old Town on your way to catch the sunset at Mallory Square. Experience these kinds of days (and nights) at SOUTHERNMOST PALMS, a beautifully renovated townhome, located at The Foundry

Southernmost Palms

Townhome

$399^.00 - $1,573^.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

New Property

Fabulously Fresh New Property!!

Cassie's Paradise

Estate

$3,800^.00 - $8,755^.00 / per night

4 bedrooms

3 baths

10 guests

Don't miss an exceptional opportunity to spend your Key West stay on the grounds of an incredible estate property in the most ideal Old Town location you could imagine. DARLING OF DUVAL is a two-story guest cottage that offers many of the essentials and comforts of a luxury hotel plus the added benefits of an in-home washer & dryer, a private p

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Darling of Duval

Cottage

$425^.00 - $2,400^.00 / per night

Located in Truman Annex, a gated community with some of the most impressive homes in Key West, this exceptional home stands out from all the rest. NOONA'S MANSION is nestled in a quiet cul-de-sac facing the ocean on a beautifully landscaped piece of property. This impressive home features six spacious bedrooms, a fully equipped kitchen, a stunning

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Noona's Mansion

Private Home

$1,500^.00 - $7,676^.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 - $7,626^.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

$333^.00 - $1,128^.00 / per night

You don’t often find new construction in Old Town, the historic district of Key West known for classic conch homes and walkable streets, but recently a spectacular new home was built smack dab in the middle of it all. CASITA OLIVIETTA is a newly built breathtaking home that allows you to enjoy the luxury of brand-new construction in the prime locat

Monthly Rental

Casita Olivietta

Private Home

$199^.00 - $805^.00 / per night

3 bedrooms

4 baths

8 guests

LA PETITE PENTHOUSE is a jewel-like second-story condo in the Shipyard at the Truman Annex, a gated community located in the very heart of Old Town Key West. You'll be just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have all of the peace and quiet that comes with a gated community.THE LIVING A

La Petite Penthouse

Condo

$269^.00 - $1,333^.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 - $1,680^.00 / per night

In Key West, every day is a celebration of what makes Summer such a beloved season - warm weather, no agendas, and spending quality time with family and friends. "Summer Solstice" provides the perfect setting for a large group looking to enjoy exactly that. As a combination of two side-by-side private homes located in the heart of Old Town, "Summer

Summer Solstice

Compound

$1,350^.00 - $8,009^.00 / per night

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

$625^.00 - $3,938^.00 / per night

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