Key West Vacation Rentals: Explore Paradise


Properties Available 144 properties available
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
Hot HOT 27
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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)
Swept Away
Private Home Pet Friendly
$200.00 - $636.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (8)
This freshly renovated condo is located at 1800 Atlantic Blvd on the beach, just steps from the Atlantic Ocean and sand in your toes. Enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling sliding glass doors, or while sitting on your private balcony surrounded by the palm tree tops. DRIFTWOOD DREAMS is locate
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)
Driftwood Dreams
Condo
$144.00 - $445.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (4)
Life in the Florida Keys is all about spending time outdoors, indulging in the things you love with the ones you love; and BLUE HORIZON is the perfect vacation home to experience Keys living for yourself. Whether your ideal day is floating around the large pool with a cold drink in hand, cruising the waters of the Lower Keys in your boat, or gather
Hot HOT 33
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)
Blue Horizon
Private Home Pet Friendly
$295.00 - $1,395.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
OASIS ON OLIVIA is the perfect setting for a large group looking to experience a month in Key West in style. As a combination of two side-by-side private homes located in the heart of Old Town, OASIS ON OLIVIA offers a prime location and plenty of comfortable accommodations for everyone, as well as numerous luxuries, including two private heated po
Oasis on Olivia
Compound Pet Friendly
Bedrooms 9 bedrooms
Bathrooms 9 baths
Guests 20 guests
Coordinating the entire gang for a dream Key West wedding, reunion, or simply a vacation of a lifetime is hard enough... let Last Key Realty make the accommodations easy for you. ALL TOGETHER NOW is an entire block of private homes just steps from Duval Street, all yours to enjoy and with everything needed for a large group getaway: a total of thir
All Together Now
Compound Pet Friendly
$2,185.00 - $11,339.00 / per night
Bedrooms 13 bedrooms
Bathrooms 13 baths
Guests 32 guests
Rating 5 (5)
You have many choices when choosing where to stay in Key West, but the most unique way to get an authentic Key West experience is by spending your vacation in a classic conch cottage smack dab in the heart of Old Town. You know what they say - “In a world full of apples, be a pineapple.” Whether you’re on a writer’s retreat or simply need an escap
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 Poetic Pineapple
Private Home Pet Friendly
$165.00 - $557.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (2)
Located on Solares Hill in the heart of Old Town, HAVANA HOUSE captures the simple elegance of Key West's Conch homes of the fifties, when it was still possible to sail to Havana.THE LIVING AREA...The living room of HAVANA HOUSE has a vaulted ceiling, with walls of Dade County Pine. There is a large flat screen TV and comfortable seating for everyo
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)
Havana House
Private Home Pet Friendly
$210.00 - $915.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 (18)
If you’ve recently heard the Siren’s call beckoning you to Key West, it might be because you were drawn by the SIREN’S SERENADE luxurious interior, lush private backyard, and dream-like location. The moment you enter the gate, you’ll meet the Siren posed in her tropical garden. You’ll come around the lavish and very private pool area to enter this
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Siren's Serenade
Private Home
$999.00 - $4,975.00 / per night
Bedrooms 5 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (3)
ATLANTIC REFLECTIONS is a newly renovated water view condo that has been meticulously furnished with a modern tropical feel, with spectacular views of the neighboring nature preserve and the ocean beyond, with no end in sight. You'll be able to enjoy those famous Key West sunsets from the living room, and sunrise shadows from your bedroom balconies
Atlantic Reflections
Condo
$300.00 - $1,837.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (111)
With a sense of gracious royalty, QUEEN OF LOUISA will treat you to an unforgettable stay in Key West. Her ideal location, modern interior, private pool and thoughtful touches throughout will ensure you and your group have everything you could want in a vacation rental. QUEEN OF LOUISA offers cozy bedrooms, a fully stocked kitchen and a fantastic o
Queen of Louisa
Private Home Pet Friendly
$625.00 - $3,938.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 12 guests
Rating 5 (40)
Finally, a large vacation home where every member of the family will be happy. From the vaulted living room with three couches and a giant 60-inch TV, to the kitchen large enough for a whole team of chefs to prepare dinner, CASA OLIVIANA has it all.THE LIVING AREA...The aforementioned living room is truly big enough for the whole family. The only d
Hot HOT 26
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)
Casa Oliviana
Private Home Pet Friendly
$395.00 - $1,508.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (14)
Finding high-end accommodations for a large group vacation can be a challenge... let Last Key Realty make it easy for you with this one-of-a-kind compound. A ROYAL AFFAIR is the combination of three homes that offer everything a large group could desire in a Key West vacation home - a total of eleven bedrooms, twelve full bathrooms, three open livi
A Royal Affair
Compound Pet Friendly
$1,800.00 - $8,776.00 / per night
Bedrooms 11 bedrooms
Bathrooms 12 baths
Guests 34 guests

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