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 154 properties available
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 Rating 5 (255)
According to the classic song, the best remedy for a belly ache is to "put de lime in de coconut and drink 'em bot' up." Last Key Realty now has the best remedy for finding comfortable accommodations for a large group vacationing in Key West: Reserve THE LIME & THE COCONUT and let us handle de rest! THE LIME & THE COCONUT is a compound of t
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The Lime & The Coconut
Compound Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half-Bathroom 2 half-baths
Guests 16 guests
Rating Rating Rating Rating 4.9 (88)
FOLLOW THE SUN is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own 28-foot balcony. You'll be able to enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling glass doors. FOLLOW THE SUN is located in an upscale private community within walking or biking distance to all of your f
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Follow the Sun
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (257)
Key West has a unique way of appealing to anyone and everyone that visits the island, and it's easy to see why: the laid-back way of life, the historic charm and walkability of Old Town, and the overall 'good vibes' that the island has to offer those needing an escape from the day to day hustle and bustle of the real world. These same appealing cha
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Good Vibrations
Private Home Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating 4.9 (202)
This freshly renovated condo is located at 1800 Atlantic Blvd on the beach, just steps from the ocean and sand in your toes. You'll be able to enjoy quiet afternoons at CONCH IN THE TREETOPS with those balmy Key West breezes wafting through the floor-to-ceiling glass doors, while sitting on your private balcony surrounded by the palm tree tops. CON
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Conch in the Treetops
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (382)
A trip to Key West is like a breath of fresh air! The sounds of rustling palm trees, the scent of fragrant flowers and the smell of salt air are the rejuvenation that only the tropics can provide. This home is a breath of Key West fresh air, or BRISA FRESCA, a timeless, beach-inspired home that seems to be straight out of the pages of Coastal Livin
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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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Brisa Fresca
Private Home
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (278)
OCEANFRONT OASIS is a boater’s paradise featuring incredible views, modern decor, and dockage that can handle a mini yacht. This five-bedroom home provides the ultimate escape for those needing a break from their fast-paced everyday life. Imagine yourself relaxing in the pool, soaking up some sun as you gaze across the endless ocean. When it’s tim
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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)
Oceanfront Oasis
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Oceanfront Oasis
Private Home Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (1)
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)
Sundrenched Reflections
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Sundrenched Reflections
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (10)
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 (278)
Welcome to VILLA PARADISO, an elegant single-story home meticulously furnished in the classic British Colonial style. The moment you walk in the front door, you’ll feel the embrace of its Old World comfort as you pass through the bright and airy living room into the updated kitchen, and out back to your private backyard oasis. No expense was spared
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Villa Paradiso
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating Rating Rating Rating 4.5 (4)
Dreaming of a large group getaway in Old Town Key West, but struggling to find a single home that offers both luxury and enough space for everyone? The solution is THE EGRET & THE SANDPIPER — two side-by-side, luxury townhomes offering a combined total of 6 bedrooms and 6 bathrooms, multiple living areas, two private saltwater pools, and a prim
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The Egret & The Sandpiper
Compound Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half-Bathroom 2 half-baths
Guests 14 guests
The sound of steel drums, the warm breeze off the water, the palm trees rustling in the sky… the essence of the Caribbean awaits in Key West for your next private vacation. This classic island townhome is located within Truman Annex, Key West's most exclusive gated community. From the Tommy Bahama furnishings and island inspired décor to the tropic
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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)
Caribbean Charm
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Caribbean Charm
Townhome
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (83)

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