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 156 properties available
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 Pet Friendly
$625.00 - $3,039.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (316)
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
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 - $682.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
THE COZY STARFISH is a newly furnished and decorated first floor condo located in the Truman Annex, a private gated community situated in the heart of the island. Despite being only steps away from all that Old Town Key West has to offer, THE COZY STARFISH is a peaceful retreat within a private gated community that offers access to a large, shared
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 Cozy Starfish
Condo
$260.00 - $930.00 / per night
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating Rating Rating Rating Rating 5 (9)
As Neptune was known as the Roman God of the Sea, NEPTUNE'S PENTHOUSE is known as the crown jewel of the 1800 Atlantic complex overlooking the Sea. This Penthouse Condominium has a lavish wrap-around balcony that overlooks the Atlantic Ocean and Community Pool below. You'll be able to enjoy the refreshing Key West breezes from atop your own private
Construction Notice Construction Notice
Construction Notice
There will be concrete restoration of every balcony in this complex through Summer 2026. This construction WILL impact your stay. Call us at 305-292-6266 prior to making a reservation.
Neptune's Penthouse
Condo
$333.00 - $1,602.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (258)
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)
Throughout Key West you'll find subtle touches of coconuts; from the towering coconut palms nestled throughout the streets of Old Town to folks sipping from fresh coconuts while soaking up the sun, and now, you can add THE TOASTED COCONUT to that list. THE TOASTED COCONUT is a rare gem in the heart of Old Town Key West that captures the essence of
Hot HOT 41
The Toasted Coconut
Private Home Pet Friendly
$500.00 - $2,422.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (146)
If you’re looking for the perfect place to spend your month in Key West, look no further than KOKOMO & TORTUGA at Seaport Inn! KOKOMO & TORTUGA is the combination of two ground level units at the historic Seaport Inn that are right across the hall from each other. This is the perfect arrangement for a pair of couples or a family looking to
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)
Kokomo & Tortuga
Condo
$250.00 - $765.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Formerly known as Playland in Paradise, the ultimate Keys vacation awaits you at BAYPOINT OASIS! This spacious waterfront property is perfect for large groups, featuring an open floor plan, six bedrooms, including three master suites, and expansive outdoor space. BAYPOINT OASIS offers every amenity you could ask for in a vacation home… and then som
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)
Baypoint Oasis
Private Home Pet Friendly
$255.00 - $913.00 / per night
Bedrooms 6 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (6)
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
Looking to make a big ‘splash’ for your next tropical vacation? MERMAID MAGIC is your answer! This newly built elevated 2 bedroom home offers incredible views and easy access to the beautiful waters of the Florida Keys. In addition, you’ll have access to the wonderful on-site amenities offered at Venture Out Resort: a heated 80-foot pool with large
Mermaid Magic
Private Home
$300.00 - $925.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (114)
THE GILDED PINEAPPLE is a classic Key West home located on one of the most desirable streets in Old Town. This completely renovated, historic home gets its’ name from the elegant, oversized golden door knocker shaped like a pineapple that graces the front door – one of the many subtle touches that adds to the charm. THE GILDED PINEAPPLE features 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)
The Gilded Pineapple
Private Home Pet Friendly
$400.00 - $1,110.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests

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