Find Your Ideal Key West Vacation Home

Your Island Getaway Awaits

At Last Key Realty, we love Key West. We are your top choice for finding houses to rent in Key West. Need a small place for a romantic trip? Or a big house for your family? We have options that will suit all of your needs while perfectly capturing the spirit and joy of Key West.

Our houses are comfy and have a local style. You'll find our rentals in the best areas of Key West, from the historic streets of Old Town to the homes and condos on 1800 Atlantic.

Want to see all of our vacation rentals on the island? Check out our Key West Vacation Rentals page. Want a pet-friendly place near Duval Street? Or a beachfront house with an ocean view near the Truman Annex? We have the perfect rental for your Key West trip.


Properties Available 94 properties available
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 - $3,010.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (87)
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 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)
Island Bliss
Private Home Pet Friendly
$225.00 - $760.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Key West is known for all things lime: Key Lime Pies, Margaritas, and now, THE ZESTY LIME, a rare gem in the heart of Old Town Key West that captures the essence of classic Key West in a completely renovated modern design. THE ZESTY LIME includes all of the coveted amenities of a vacation home: a spacious living area, an ideal bedroom and bathroom
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The Zesty Lime
Private Home Pet Friendly
$500.00 - $2,606.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (158)
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 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)
The Wicked Tuna
Private Home Pet Friendly
$225.00 - $699.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Located in the Truman Annex, a gated community with some of the most impressive homes in Key West, this meticulously furnished estate occupies an entire block, making it the largest single property in the Annex. Formerly referred to as "Plantation Tropicale," with three dwellings, two kitchens (one indoor, one outdoor), a very large pool and enoug
Hot HOT 28
2026 Changes 2026 Changes
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.
The Royal Compound
Compound Pet Friendly
$1,500.00 - $5,944.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (60)
Hunting for the perfect Key West vacation home can feel like a daunting task. However, once you discover TRUMAN’S TROVE, you’ll know that you’ve struck gold! This two-story private home has been beautifully furnished and designed to the highest standard. In addition, TRUMAN’S TROVE offers an ideal location within Truman Annex, Key West’s most exclu
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2026 Changes 2026 Changes
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.
Truman's Trove
Private Home
$475.00 - $1,531.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (5)
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 Pet Friendly
$345.00 - $1,264.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (33)
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 Pet Friendly
$675.00 - $4,052.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (222)
Escape the “changing tides” of your day-to-day routine by spending a month in the Keys. MARINER’S HIDDEN HAVEN provides an ideal island setting for re-centering your compass by way of your own private waterfront retreat. Picture mornings sipping coffee on the dock, lazy days by the pool, and beautiful sunsets on your boat. The home’s open layout an
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)
Mariner's Hidden Haven
Private Home Pet Friendly
$175.00 - $551.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (4)
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 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)
The Artists' Muse
Private Home
$350.00 - $990.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (13)
DOS CASITAS is the perfect property for a group of friends or a family that wants to experience Key West together in comfortable neighboring accommodations. DOS CASITAS is a cleverly named combo of two side-by-side private homes with a total of five bedrooms, five bathrooms, and an unbeatable location - half a block off Duval Street on Catherine St
New Property New Property
New Property
Dos Casitas
Compound Pet Friendly
$800.00 - $4,866.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 14 guests
CASA VICTORIA, located in the heart of Old Town just two blocks from Duval Street, is a large 5 bedroom home built with the charm and quirkiness of early 20th century Key West. Dating back to the Cigar Manufacturers' era, CASA VICTORIA exudes the classic Old Town style that makes Key West such a unique vacation experience. This authentic Conch Hous
Hot HOT 39
Casa Victoria
Private Home Pet Friendly
$995.00 - $5,007.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (371)

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