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
Hidden amongst the thick of Old Town Key West, within Truman Annex, Key West's most exclusive gated community, lives a 'gem' of a home that will surely capture your heart's desire from the moment you lay eyes on it. JASMINE JEWEL is a two-story private home that not only transcends island living at its finest but also offers an ideal location for e
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Jasmine Jewel
Private Home
$600.00 - $2,627.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (36)
AZURE DAYDREAM, a beautifully renovated waterfront home located 25 miles north of Key West, epitomizes Florida Keys living at its finest. From spending your days on the boat exploring the Lower Keys, to hosting the ultimate family game night in the game room, there’s no shortage of fun to be had at AZURE DAYDREAM. This 4-bedroom home was recently u
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New Property New Property
New Property
Fabulously Fresh New Property!!
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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)
Azure Daydream
Private Home Pet Friendly
$199.00 - $1,101.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
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 - $1,001.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (105)
This renovated Old Town estate is designed for the real downtown experience in the Conch Republic, but in a large home-base all your own. SWEET HOME ANGELITA is located right in Old Town, half a block away from Duval Street and smack dab in the center of the entertainment district. You couldn't be any closer to the late-night scene and attractions
Sweet Home Angelita
Private Home Pet Friendly
$560.00 - $3,922.00 / per night
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 5 (52)
OLD TOWN OASIS is back! After three years out of the rental program, this luxurious condo has returned, with all the same elegance enjoyed by many guests since 2004, and with many improvements.You’ll be staying right near the ocean in Old Town but with all the quiet and solitude of an exclusive gated community. The Green Parrot (oldest blues bar in
Old Town Oasis
Condo
$325.00 - $1,337.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (23)
Travelers from around the world would agree spending a month in Key West is truly a magical experience, especially when you find two classic conch homes made into one. This cozy compound perfectly captures the magic of the island, with its beautiful Dade County Pine walls, tropical decor, and the plunge pool waiting just outside. MARGARET’S MAGIC
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)
Margaret's Magic Compound
Compound Pet Friendly
$318.00 - $1,156.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
For a truly over-the-top Key West stay with your entire group, whether that be the whole family or your closest friends, STAR OF THE SEAPORT has the location, amenities, layout, and extra guest service to help host the island trip you envision. STAR OF THE SEAPORT is a luxurious private estate that occupies an expansive space on an iconic street in
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Star of the Seaport
Private Home Pet Friendly
$1,200.00 - $5,371.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (84)
Seals & Crofts said it best: ‘Diamond Girl, you sure do shine.’ Formerly known as Seventh Heaven, DIAMOND GIRL is a stunning two-story private home that epitomizes island living, with its’ distinct exterior eyebrow design, ample indoor and outdoor living space, and comfortable accommodations. Once here you’ll quickly realize this peaceful oasis
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Diamond Girl
Private Home
$850.00 - $3,767.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (5)
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 Pet Friendly
$800.00 - $4,834.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (7)
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 - $1,882.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (24)
Traveling to Key West with a group deserves the ultimate vacation rental home: plenty of space to stretch out and enjoy time together, separate rooms and bathrooms to enjoy privacy, a private saltwater pool and of course, outdoor lounge area off street parking for scooters, and bicycles. THE SMILING IBIS checks all of these boxes, and more. Located
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The Smiling Ibis
Townhome Pet Friendly
$400.00 - $2,875.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (145)

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