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
Experience the blend of historic charm and modern conveniences at TASTE OF HAVANA. This 2-bedroom, 2-bathroom cottage located ON world-famous Duval Street offers a front-row seat to the vibrant energy of Key West while providing a private pool and off-street parking for those who appreciate the finer things that come with island living. From the pr
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Taste of Havana
Private Home Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating Rating Rating Rating Rating 5 (4)
Located in Truman Annex, a gated community with some of the most impressive homes in Key West, this exceptional home stands out from all the rest. NOONA'S MANSION is nestled in a quiet cul-de-sac facing the ocean on a beautifully landscaped piece of property. This impressive home features six spacious bedrooms, a fully equipped kitchen, a stunning
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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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Noona's Mansion
Private Home
Bedrooms 6 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (128)
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
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POOL CLOSED - AUGUST 2026
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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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Saltwater Harmony
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating Rating Rating Rating 4.9 (98)
SWEPT AWAY is a meticulously renovated and decorated one-story private home with a refreshing mix of that classic conch home feel we all adore and a new coastal style. This conch cottage has an open living plan and a lovely backyard garden area with a private pool, ideal for relaxing in your oasis just blocks from the famous sites of Old Town Key W
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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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Swept Away
Private Home Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating Rating Rating Rating Rating 5 (9)
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 outdoor lounge area, and off street parking for scooters, and of course, bicycles. THE CONTENTED CRANE checks all of these boxes, and more.
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The Contented Crane
Townhome Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating 4.9 (152)
SUNDRENCHED REFLECTIONS is very close to Old Town, with access to all the attractions that Key West has to offer. Yet, you'll be in your own world with a large sundrenched balcony overlooking Florida Bay and the Gulf of Mexico beyond. THE PRIVATE GATED COMMUNITY... Sunset Marina is a gated community located on Stock Island, right off the entrance t
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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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Sundrenched Reflections
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (5)
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
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Neptune's Penthouse
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (159)
GULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of GULFSIDE VISTAS, and two spacious balconies as well.Compliance with Truman Annex Community Rules & Regulations is expected of all
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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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Gulfside Vistas
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (126)
This ultimate Key West dream home is nestled in the highly desirable residential Old Town neighborhood of Solares Hill, just a quick walk from Duval Street and the Historic Seaport areas. No expense has been spared in upgrading and furnishing VILLA OLIVIETTA; the most up-to-date appliances and technology can be found in each room. The comfortable a
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Villa Olivietta
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (3)
This precious 2 bedroom cottage with its coral front door will charm you from the moment you walk in the front gate. The front porch is private, for some quiet time reading a book. Inside, you'll see that PUERTA CORALINA reflects the simpler side of tropical living but with some useful updates.THE LIVING AREA...The living room of PUERTA CORALINA is
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Puerta Coralina
Private Home Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (292)
A stay in Key West calls for a light and airy oasis, with breathtaking water views and an easy beach location to fully enjoy the ultimate of island life in America. RIVIERA AMERICANA is located in an upscale private community within walking or biking distance to all of your favorite Key West spots, including beaches, restaurants, shopping, and the
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Riviera Americana
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating Rating Rating Rating 4.9 (172)
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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Soul of Duval
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating Rating Rating Rating 4.9 (133)

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