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 155 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 - $2,945.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (87)
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 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 Three Mermaids
Compound Pet Friendly
$500.00 - $1,287.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 12 guests
Look for the coral pink “Sugarpoppy” door on this quintessential conch cottage and you’ll know you’ve found a special vacation home. This cozy little gem is located on a quiet one-way street just a block off of Duval. In addition to the superb location, this one-story home also offers top-notch amenities. With a dreamy front porch, a private heate
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)
Sugarpoppy Cottage
Private Home Pet Friendly
$200.00 - $715.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (9)
DOCKSIDE DAYDREAMS is a tastefully decorated villa located in the Coconut Mallory Resort & Marina with two large community pools with plenty of chaises. There are also boat slips available on-site for rent if you want to bring your boat.THE LIVING AREA...This modern home has just undergone a complete renovation to a very high standard. No expen
Dockside Daydreams
Townhome
$200.00 - $796.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (184)
Among the many hidden treasures of Old Town Key West, lives a charming loft-style condo that will melt your heart from the moment you enter. SOUTHARD PEARL is a 2 bedroom second floor condo located in Southard Square, an intimate community located in the heart of the island - a few blocks from Mallory Square, Duval Street and all the attractions Ke
New Property New Property
New Property
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)
Southard Pearl
Condo Pet Friendly
$138.00 - $539.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
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
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.
Grand Key Oasis
Compound
$850.00 - $3,366.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (10)
SEA CAPTAIN'S HAVEN is an immaculately furnished villa at the Porter Court Complex in Truman Annex, Key West's most desirable gated community, right in the middle of Old Town. At SEA CAPTAIN'S HAVEN, you'll be close to all of Key West's best restaurants and attractions, including Mallory Square and Fort Zachary Taylor State Park.THE LIVING AREA...S
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.
Sea Captain's Haven
Townhome
$315.00 - $1,168.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (117)
Sometimes in life a 'stroke of good fortune' leads you to discover something so delightful at a moment when you're not even looking for it. When strolling through the streets of Old Town Key West, you may be fortunate enough to stumble upon a home with the perfect combination of quintessential charm and the conveniences of modern amenities. CASA SE
Hot HOT 29
Casa Serendipity
Private Home Pet Friendly
$444.00 - $2,395.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (221)
SALTWATER HARMONY is a cozy and beautifully furnished first-floor condo in the Shipyard at the Truman Annex, an exclusive gated community located in the heart of Old Town Key West. You'll be just steps from Mallory Square, Duval Street and all of Key West's major attractions, and yet you'll have all of the peace and quiet that comes with a gated co
Hot HOT 138
Saltwater Harmony
Condo
$275.00 - $919.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating Rating Rating Rating Rating 5 (170)
When the ‘Welcome to Key West’ sign hits your eye, like a big pizza pie, THAT’S AMORE! If you’ve ever visited Key West, you know how easy it is to fall in love with the charm of this little island. It’s even easier to fall in love when staying in a lavishly decorated and furnished, fully stocked, historic home in the heart of Old Town, and THAT’S A
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)
That's Amore!
Private Home
$333.00 - $1,125.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 6 guests
VILLA BAHAMA is located at The Foundry in the Truman Annex, Key West's most exclusive gated community. You'll be just around the block from Mallory Square, Duval Street and all the attractions Key West has to offer, yet you'll benefit from the peace and quiet that the Truman Annex is known for. Smoking is not permitted in any Last Key Realty home.
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.
Villa Bahama
Townhome
$350.00 - $1,069.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (221)
Life in the Florida Keys is all about spending time outdoors, indulging in the things you love with the ones you love; and BLUE HORIZON is the perfect vacation home to experience Keys living for yourself. Whether your ideal day is floating around the large pool with a cold drink in hand, cruising the waters of the Lower Keys in your boat, or gather
Hot HOT 30
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)
Blue Horizon
Private Home Pet Friendly
$295.00 - $992.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (1)

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