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

You have many choices when choosing where to stay in Key West, but the most unique way to get an authentic Key West experience is by spending your vacation in a classic conch cottage smack dab in the heart of Old Town. You know what they say - “In a world full of apples, be a pineapple.” Whether you’re on a writer’s retreat or simply need an escap

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 Poetic Pineapple

Private Home

$150^.00 - $550^.00 / per night

There’s no doubt you’ve heard of Duval Street; phenomenal restaurants, eclectic shops and legendary nightlife. This immaculate condo is just a half block away, giving you access to everything Duval Street has to offer while still allowing you to get a restful night’s sleep. SOUL OF DUVAL truly captures the essence of what makes Key West so special,

Soul of Duval

Condo

$240^.00 - $1,214^.00 / per night

THE DUKE & THE DUCHESS is a compound fit for a Queen, her King, and their whole court! These newly built, professionally designed side-by-side homes have everything you could desire for a large group vacation - a prime location, coveted amenities, and plenty of space. Your stay at the THE DUKE & THE DUCHESS also includes Last Key Realty's F

The Duke & The Duchess

Compound

$1,200^.00 - $5,635^.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 - $6,118^.00 / per night

Finding a compound like THE THREE MERMAIDS in Key West is as rare as finding actual mermaids! From the pristine, modern decor, to the fun, nostalgic appliances and the ample amount of space in an ideal Old Town location, this compound is truly a one-of-a-kind. Featuring 3 stunning, freshly-built homes on one lot, with a beautiful swimming pool betw

Monthly Rental

The Three Mermaids

Compound

$500^.00 - $1,293^.00 / per night

SWEPT AWAY is a meticulously renovated and decorated one-story private home with a refreshing mix of that classic conch home feel we all adore and a new coastal style. This conch cottage has an open living plan and a lovely backyard garden area with a private pool, ideal for relaxing in your oasis just blocks from the famous sites of Old Town Key W

Monthly Rental

Swept Away

Private Home

$172^.00 - $575^.00 / per night

The sound of steel drums, the warm breeze off the water, the palm trees rustling in the sky… the essence of the Caribbean awaits in Key West for your next private vacation. This classic island townhome is located within Truman Annex, Key West's most exclusive gated community. From the Tommy Bahama furnishings and island inspired décor to the tropic

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.

Caribbean Charm

Townhome

$350^.00 - $1,064^.00 / per night

Located across the street from Blue Heaven, above the delicious La Creperie French Cafe, sits THE PIRATE’S PENTHOUSE. This hidden gem is ideally located in the heart of Bahama Village and within walking distance to everything Duval has to offer. THE PIRATE’S PENTHOUSE has touches of maritime decor sprinkled throughout this spacious condo, complet

The Pirate's Penthouse

Condo

$333^.00 - $1,683^.00 / per night

If your idea of a vacation includes pampering yourself and indulging in the finer things in life, then a stay at the DUCHESS OF CATHERINE will be your cup of tea. This newly built, professionally designed home is fit for a King and offers plenty of space for all the members of your court. Located on Catherine Street, just steps from Duval Street, y

HOT 30

Duchess of Catherine

Private Home

$850^.00 - $3,884^.00 / per night

SPIRIT OF KEY WEST was originally built in 1893 and features that authentic Key West charm found in other historic properties such as Hemingway’s House, Asa Tift’s manor and Truman’s Little White House. The vaulted ceilings and Dade County Pine walls harken back to a time when the cigar industry was booming and Key West featured more millionaires p

Monthly Rental

Spirit of Key West

Private Home

$385^.00 - $1,140^.00 / per night

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 31

The Royal Compound

Compound

$1,350^.00 - $5,951^.00 / per night

SOUTHERNMOST HOSPITALITY V 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 form

Southernmost Hospitality V

Private Home

$800^.00 - $4,772^.00 / per night

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