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.


Properties Available 145 properties available
MODERN MAJESTY is a stunning, freshly renovated three-bedroom condo that checks every box for the perfect vacation rental. This large unit is laid out over one floor, meaning you don’t have to worry about stairs. The three bedrooms are luxuriously appointed suites, each with their own en-suite bathroom. The kitchen is as functional as it is beautif
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)
Modern Majesty
Condo
$295.00 - $1,034.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (1)
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 - $1,285.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (45)
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
Caribbean Charm
Townhome
$350.00 - $1,274.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (34)
In the Historic Seaport area of Old Town, there is a house that will behold your eye. At first glance you'll see that HEAVENLY ZEN is beautifully maintained with carefully tended landscaping; however, nothing will prepare you for what is inside. As you walk in, you will feel an immediate sense of peace and relaxation. All of the spaces in this meti
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)
Heavenly Zen
Private Home Pet Friendly
$375.00 - $1,309.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
A highlight of any Key West vacation is exploring the island and discovering for yourself Old Town's most treasured restaurants and attractions. The newest discovery awaiting you is a precious ‘gem’ of a home tucked away in a quiet enclave within Truman Annex, Key West’s most exclusive gated community. SALTWATER SAPPHIRE is a newly renovated two-st
Saltwater Sapphire
Private Home
$475.00 - $1,662.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (29)
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 - $2,065.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (22)
If you’ve recently heard the Siren’s call beckoning you to Key West, it might be because you were drawn by the SIREN’S SERENADE luxurious interior, lush private backyard, and dream-like location. The moment you enter the gate, you’ll meet the Siren posed in her tropical garden. You’ll come around the lavish and very private pool area to enter this
Siren's Serenade
Private Home
$999.00 - $4,107.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (3)
Dreaming of a large group getaway in Old Town Key West, but struggling to find comfortable accommodations for your whole gang? The dream becomes a reality with THE IBIS & THE CRANE: two side-by-side townhomes with six bedrooms, six bathrooms, and a prime Old Town location perfect for enjoying all that Key West has to offer. The perks of reservi
The Ibis & The Crane
Compound Pet Friendly
$800.00 - $6,282.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 16 guests
Rating 5 (46)
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 Pet Friendly
$1,350.00 - $8,098.00 / per night
Bedrooms 9 bedrooms
Bathrooms 9 baths
Guests 22 guests
Rating 5 (4)
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
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Fabulously Fresh New Property!!
Cassie's Paradise
Estate Pet Friendly
$3,800.00 - $8,741.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
HARBORSIDE HARMONY is the epitome of luxurious waterfront living! With scenic views of the Gulf from the living area and private balcony, coupled with a spacious layout and island-style furnishings, this gorgeous condo is the ideal place to call home during your Key West vacation. Best of all, HARBORSIDE HARMONY is located in the exclusive gated co
Harborside Harmony
Condo
$400.00 - $1,694.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (2)
This colorful two story Old Town cottage is just right for a delightful stay in the Conch Republic. VILLA CUBANA is located right in Old Town, one block away from Duval Street and smack dab in the center of the fun. You couldn't be any closer to the nightlife and attractions of downtown, yet you are tucked away in a quiet gated community you would
Villa Cubana
Townhome
$300.00 - $1,670.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (78)

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