Key West Luxury Rentals

Welcome to Elegance in Key West: Choose Your Luxury Rental and Book Today!

Experience the pinnacle of opulence with Key West luxury rentals that feature unmatched amenities such as private pools, hot tubs, captivating views, and gourmet kitchens. Every stay with us grants you access to a complimentary concierge, ensuring your Key West vacation is a seamless blend of comfort and indulgence.

Group travels become unforgettable with our Key West Compound Rentals, offering two or more adjoining properties. If you're journeying with a furry companion, our pet-friendly Key West luxury house rentals are a perfect match.


Properties Available 154 properties available
A stay at the DUKE OF CATHERINE is fit for a Queen to bring her King! From the crisp, clean decor to the large hot tub and the spacious master bedroom, the DUKE OF CATHERINE has everything his Majesty could desire. This freshly built, professionally designed home is the perfect size for a weekend rendezvous or an extended stay with the royal family
Hot HOT 38
Duke of Catherine
Private Home Pet Friendly
$375.00 - $1,780.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (40)
Get the gang together for the ultimate Key West Beach Vacation in a one-of-a-kind giant of an island beach house, BELLE OF THE BEACH. Fully renovated to exceed the highest level of quality and comfort as a large family vacation home, this private estate occupies an entire corner lot, just a block from Smathers Beach. This stilted home allows for a
Hot HOT 35
Belle of the Beach
Private Home Pet Friendly
$1,100.00 - $4,382.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half-Bathroom 1 half-baths
Guests 16 guests
Rating 5 (121)
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
Hot HOT 54
The Lime & The Coconut
Compound Pet Friendly
$1,000.00 - $5,080.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half-Bathroom 2 half-baths
Guests 16 guests
Rating 5 (81)
A highlight of any Key West vacation is exploring the island and discovering for yourself Old Town's most treasured restaurants and attractions. The newest discovery awaiting you is a precious ‘gem’ of a home tucked away in a quiet enclave within Truman Annex, Key West’s most exclusive gated community. SALTWATER SAPPHIRE is a newly renovated two-st
Hot HOT 25
Saltwater Sapphire
Private Home
$475.00 - $1,604.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 2 half-baths
Guests 6 guests
Rating 5 (62)
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
Hot HOT 30
Brisa Fresca
Private Home
$860.00 - $2,446.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (269)
CASA AVILA combines a rich history with a desirable Old Town location. Located two blocks from both the waterfront and Duval Street, this beautiful home is considered one of Old Town's original Grande Dames and proudly displays a historical preservation star. CASA AVILA was Key West's first prominent art gallery and one of the original homes in Old
Hot HOT 34
Casa Avila
Private Home
$300.00 - $915.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
NATURE'S EDGE is a well maintained condo that is located at 1800 Atlantic Blvd on the beach, just steps from the ocean and sand in your toes. You'll enjoy peace and quiet on your balcony, with the Key West Nature Preserve just outside your door. NATURE'S EDGE is located in an upscale private community within walking or biking distance to all of you
Hot HOT 34
Nature's Edge
Condo
$200.00 - $1,200.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (173)
Traveling with a large group requires a special home. To maximize comfort, large common areas are offered both indoor and outdoor. Private bedroom accommodations with en-suite bathrooms and TVs are a must. And don't forget about the location! This home is easily accessible to the favorites of Old Town for when the group (finally) reaches a decision
Hot HOT 42
La Grande Reunion
Private Home Pet Friendly
$400.00 - $1,315.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating 5 (28)
Get out of the turtle pond and make a splash in the ocean with your month stay at TORTUGA SUITE at the Seaport Inn! Within in quick walk to great sunsets, food, drinks, and attractions, you can still move at a “tortuga’s” pace and see it all! You can relax with ease as you will have access to Last Key Realty’s Five-Star Guest Services and Complimen
Hot HOT 34
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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)
Tortuga Suite
Condo
$225.00 - $547.00 / per night
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Imagine a traditional conch home in the Solares Hill section of Old Town. MAISON TROPICALE is stunningly restored then decorated in a post-modern style with vivid colors and sophisticated decor. Every room is adorned with colorful art and has been furnished with unique show pieces. This brilliant decor is set against a backdrop of original Dade Cou
Hot HOT 40
Maison Tropicale
Private Home Pet Friendly
$250.00 - $825.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (18)
Dreaming of a large group getaway in Old Town Key West, but struggling to find comfortable accommodations for your whole gang? The dream becomes a reality with THE IBIS & THE CRANE: two side-by-side townhomes with six bedrooms, six bathrooms, and a prime Old Town location perfect for enjoying all that Key West has to offer. The perks of reservi
Hot HOT 30
The Ibis & The Crane
Compound Pet Friendly
$800.00 - $5,058.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half-Bathroom 2 half-baths
Guests 16 guests
Rating 5 (119)
Walking along Duval Street dreaming of the ideal Key West vacation destination, scanning the rooftops for possibilities, at first you’ll miss this hidden gem completely…but once you discover MAYA’S SECRET TREASURE, you will know you have found the ultimate home base to enjoy Key West. Perched above Duval Street, this beautifully modern condo offers
Hot HOT 37
Maya's Secret Treasure
Condo Pet Friendly
$599.00 - $3,306.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (146)

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