Key West Vacation Rentals

Discover the best Key West vacation rentals with Last Key Realty. Whether you're looking for a private home with a pool, a cozy condo near Duval Street, or a beachfront villa, we have options for every group and budget. Browse our complete inventory and experience Key West like a local.

Our Key West vacation rentals are hand-selected for comfort, convenience, and style. Guests enjoy private pools, spacious outdoor areas, fully equipped kitchens, and easy access to the island's top attractions. Whether you're planning a romantic getaway, a family reunion, or a group trip with friends, you'll find a perfect fit in our collection of homes and condos throughout Old Town, the Casa Marina district, and other sought-after neighborhoods.

Browse Vacation Rentals by Type

Private pool and patio area at a Key West vacation rental. The pool is surrounded by a wooden deck with lounge chairs and a table with chairs. Tropical plants and palm trees provide shade and privacy.

Private Homes 

Find your perfect home-away-from-home in Key West! Choose from cozy cottages, spacious family homes, and luxurious estates with private pools and stunning views.

Balcony with a table and chairs overlooking tropical foliage at a Key West vacation rental.

Condo Rentals 

Experience Key West living in a stylish condo! Enjoy modern amenities, breathtaking waterfront views, and easy access to the island's best attractions.

Two kayaks on a dock at a waterfront Key West vacation rental. Palm trees and boats are visible in the background.

Waterfront Rentals 

Indulge in the ultimate Key West escape with a luxurious waterfront rental. Wake up to stunning sunrises and enjoy unparalleled access to the crystal-clear waters.

Private pool and patio area at a Key West vacation rental. The pool is surrounded by a wooden deck with lounge chairs and a table with chairs. Tropical plants and palm trees provide shade and privacy.

Pet Friendly Rentals 

Bring your furry friend along and find the perfect pet-friendly getaway in Key West! Choose from charming cottages, spacious family homes, and upscale estates with room to relax and enjoy, plus features like fenced yards, private pools, and nearby pet-friendly parks and beaches.

Balcony with a table and chairs overlooking tropical foliage at a Key West vacation rental.

Beachfront Rentals 

Wake up to ocean breezes in a beachfront Key West rental! Enjoy stunning waterfront views, direct beach access, and all the modern comforts you need for a relaxing island escape — just minutes from top attractions, dining, and nightlife.

Two kayaks on a dock at a waterfront Key West vacation rental. Palm trees and boats are visible in the background.

Lower Keys Rentals 

Unplug and unwind with a Lower Keys vacation rental. From tranquil waterfront homes to secluded island retreats, enjoy peaceful mornings, vibrant wildlife, and easy access to snorkeling, kayaking, and the unspoiled beauty of the Lower Florida Keys.

Properties Available 155 properties available
Nestled in the heart of Old Town, HEMINGWAY’S HAVEN is just the spot for anyone dreaming of what Key West was like during its golden days when Ernest, Sloppy Joe, and Harry T roamed the island. This welcoming, two-story private home has been lovingly renovated and decorated, showcasing a delightful mix of classic conch style with a modern, fresh tw
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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)
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Hemingway's Haven
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (1)
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
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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)
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That's Amore!
Private Home
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 6 guests
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
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Casa Serendipity
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (179)
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
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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)
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The Gilded Pineapple
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Want to be in Key West, have access to all the fun, but not be in the middle of the crowd at the end of the day? Then step away from the hustle and bustle and come roost at… THE OSPREY’S NEST. Boasting views from your private balcony on the top floor of Sunrise Suites, 2-Bedrooms, 2-Bathrooms, and a full kitchen; THE OSPREY’s NEST has all the neces
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The Osprey's Nest
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (64)
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
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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
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Heavenly Zen
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (32)
SUNSET POINT has everything you could want in a vacation home: it is close to Old Town, so you'll be able to enjoy everything that Key West has to offer. Yet, you'll be in your own world at SUNSET POINT with a very large balcony overlooking the Florida Bay and the Gulf of Mexico beyond.THE PRIVATE GATED COMMUNITY...Sunset Marina is a gated communit
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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)
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Sunset Point
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (8)
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,
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Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating Rating Rating Rating 4.9 (133)
If you dream of waking up to expansive water views and island breezes, and walking out your front door right onto the streets of Old Town Key West in the center of it all - PROMENADE TO PARADISE is everything you are looking for. With a spacious layout, relaxed island-style furnishings, a semi-private gated pool, and three private balconies all you
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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)
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Promenade to Paradise
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (76)
Hunting for the perfect Key West vacation home can feel like a daunting task. However, once you discover TRUMAN’S TROVE, you’ll know that you’ve struck gold! This two-story private home has been beautifully furnished and designed to the highest standard. In addition, TRUMAN’S TROVE offers an ideal location within Truman Annex, Key West’s most exclu
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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)
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Truman's Trove
Private Home
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating 4.8 (9)
The moment you arrive at CASA AMARILLA and see the dual rocking chairs beckoning you to the front porch, you’ll feel the weight of the world start to lift from your shoulders as your vacation truly begins. Upon entering this adorable cottage, you’ll see the quaint interior is the perfect place to unwind, offering cozy bedrooms, a fully stocked kitc
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Casa Amarilla
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (166)
SOUTHERNMOST HOSPITALITY VII 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 for
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Southernmost Hospitality VII
Compound Pet Friendly
Bedrooms 7 bedrooms
Bathrooms 7 baths
Half-Bathroom 1 half-baths
Guests 16 guests
Rating Rating Rating Rating 4.9 (120)

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