Key West House Rentals

Discover the charm of Key West with Last Key Realty, your premier choice for Key West house rentals. Whether you're seeking a cozy bungalow for a romantic getaway or a spacious estate for a family vacation, our portfolio of properties captures the unique essence of the "Conch Republic."

At Last Key Realty, we are more than just a vacation rental broker; we are enthusiasts of all Key West offers. Our properties are thoughtfully designed and furnished to ensure you feel the comfort of home with a touch of local flair. From the historic streets of Old Town to the serene shores of 1800 Atlantic, our vacation house rentals are ideally situated in Key West's most desirable locations.

Why not take a moment to browse our complete selection of properties? Our Key West Vacation Rentals page features our entire inventory, making it easy for you to view all available options. Whether you're looking for a property near the bustling streets of Duval or a quiet retreat by Sunset Marina, you'll find that each of our homes is thoughtfully positioned to enhance your experience in Key West. Start planning your dream vacation by exploring the range of homes available through Last Key Realty today.

89 properties available

The moment you arrive at CASA AMARILLA and see the dual rocking chairs beckoning you to the front porch, you’ll feel the weight of the world start to lift from your shoulders as your vacation truly begins. Upon entering this adorable cottage, you’ll see the quaint interior is the perfect place to unwind, offering cozy bedrooms, a fully stocked kitc

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Casa Amarilla

Private Home

$451^.00 - $3,298^.00 / per night

This ultimate Key West dream home is nestled in the highly desirable residential Old Town neighborhood of Solares Hill, just a quick walk from Duval Street and the Historic Seaport areas. No expense has been spared in upgrading and furnishing VILLA OLIVIETTA; the most up-to-date appliances and technology can be found in each room. The comfortable a

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)

Villa Olivietta

Private Home

$299^.00 - $1,003^.00 / per night

For the ultimate stay in America's Paradise, what could be more perfect for your whole group than AMERICANA TROPICALE? This festive and patriotic home will promise a one-of-a-kind island experience. AMERICANA TROPICALE has 4 spacious bedrooms each complete with its own en-suite bathroom for privacy, a private saltwater pool, a fully equipped kitch

Americana Tropicale

Private Home

$625^.00 - $4,109^.00 / per night

AZURE DAYDREAM, a beautifully renovated waterfront home located 25 miles north of Key West, epitomizes Florida Keys living at its finest. From spending your days on the boat exploring the Lower Keys, to hosting the ultimate family game night in the game room, there’s no shortage of fun to be had at AZURE DAYDREAM. This 4-bedroom home was recently u

New Property

Fabulously Fresh New Property!!

Monthly Rental

Azure Daydream

Private Home

$199^.00 - $1,101^.00 / per night

4 bedrooms

3 baths

8 guests

Hidden amongst the thick of Old Town Key West, within Truman Annex, Key West's most exclusive gated community, lives a 'gem' of a home that will surely capture your heart's desire from the moment you lay eyes on it. JASMINE JEWEL is a two-story private home that not only transcends island living at its finest but also offers an ideal location for e

Jasmine Jewel

Private Home

$600^.00 - $2,695^.00 / per night

CASA AVILA combines a rich history with a desirable Old Town location. Located two blocks from both the waterfront and Duval Street, this beautiful home is considered one of Old Town's original Grande Dames and proudly displays a historical preservation star. CASA AVILA was Key West's first prominent art gallery and one of the original homes in Old

New Property

Fabulously Fresh New Property!!

Monthly Rental

Casa Avila

Private Home

$275^.00 - $915^.00 / per night

3 bedrooms

3 baths

8 guests

Imagine your whole group staying in one home, with everyone having their own private bedroom suite. At CASA SUITE CASA, all four bedrooms are laid out as suites; each with an en-suite bathroom and flat screen TV. And that's just the beginning! A large private pool surrounded by tropical gardens, an expansive living area, and an ideal location close

Monthly Rental

Casa Suite Casa

Private Home

$275^.00 - $1,000^.00 / per night

SOUTHERNMOST HOSPITALITY VII is a luxurious private estate that occupies an entire corner of Old Town's famous Duval Street, just a block from the Southernmost Point. Don't let the address fool you... this upscale home has plenty of privacy in the spacious back yard with a tall fence surrounding the large private pool. Privacy also comes in the for

Southernmost Hospitality VII

Compound

$900^.00 - $7,115^.00 / per night

BAHAMIAN BAMBOO has been painstakingly decorated and furnished in a sophisticated yet distinctive Bahamian style. Your lifestyle in this home will be very Bahamian as well, with large French doors that open up to provide seamless tropical indoor/outdoor living. The pool is just steps away from the living room sectional or the outdoor dining area. Y

Bahamian Bamboo

Private Home

$725^.00 - $3,172^.00 / per night

Get the gang together for the ultimate Key West Beach Vacation in a one-of-a-kind giant of an island beach house, BELLE OF THE BEACH. Fully renovated to exceed the highest level of quality and comfort as a large family vacation home, this private estate occupies an entire corner lot, just a block from Smathers Beach. This stilted home allows for a

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Belle of the Beach

Private Home

$850^.00 - $5,261^.00 / per night

Get the gang together for the ultimate Key West Beach Vacation in a one-of-a-kind giant of an island beach house, BEAUTY OF THE BEACH. Fully renovated to exceed the highest level of quality and comfort as a large family vacation home, this private estate occupies an entire corner lot, just a block from Smathers Beach. This stilted home allows for a

Monthly Rental

Beauty of the Beach

Private Home

$333^.00 - $1,050^.00 / per night

6 bedrooms

6 baths

12 guests

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 - $7,684^.00 / per night

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